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20 Best Winter Garden Restaurants | Winter Garden, FL

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Winter Garden’s charming and well-preserved historic downtown area is a must-visit. The streets are lined with quaint shops, boutiques, and antique stores housed in beautifully restored buildings. Strolling through the streets, visitors can admire the architecture and immerse themselves in the town’s rich history.

Founded in the late 19th century as a small agricultural community, the area was initially inhabited by Native American tribes, including the Timucua and Seminole peoples. The town as we know it today, however, began to take shape with the arrival of some of the original snowbirds in the late 1800s who established citrus farms.

While citrus had arrived with European explorers as early as the 16th century, it wasn’t until the mid-1870s that commercially growing citrus developed with William Chase and Joseph Tilden purchasing large tracts of land for citrus cultivation and the citrus industry boomed. 

These early pioneers played a vital role in shaping Winter Garden’s growth. The town thrived on the success of its citrus industry, becoming a major producer of oranges and grapefruits. With the arrival of the railroad in the late 19th century, Winter Garden gained easier access to markets, leading to further development and economic prosperity.

Over the next century, Winter Garden continued to evolve. In the early 20th century, the town experienced a boom in population as more settlers, including both farmers and workers, flocked to the area seeking opportunities in the citrus industry.

The town incorporated in 1908, marking an important milestone in its history. When you’re in town, visit the interactive fountain and splashpad in Centennial Plaza and give the kids time to cool off.  

Like many Florida towns, Winter Garden faced challenges in the mid-20th century due to freezes that devastated the citrus industry. The town adapted by diversifying its economy and embracing new opportunities. The establishment of Disney World in nearby Orlando in 1971 brought increased tourism to the region, providing a new avenue for growth and development.

Winter Garden, FL,

In recent years, Winter Garden has experienced significant revitalization and has become a popular destination for residents and visitors alike. The historic downtown area has undergone a transformation, with the preservation and restoration of its charming buildings. Today, Winter Garden’s downtown is a vibrant hub, featuring a wide range of shops, restaurants, and cultural attractions.

The town has also focused on promoting a sense of community and preserving its rich history. Events such as the Winter Garden Farmers Market and the Winter Garden Music Fest bring locals together, while the Winter Garden Heritage Foundation works to preserve and showcase the town’s historical legacy.

Winter Garden’s development over the past century is a testament to the resilience and adaptability of its residents. From its humble beginnings as a citrus farming community, it has transformed into a thriving town that balances its agricultural roots with a vibrant downtown and a diverse economy.

Winter Garden, Florida is now quite the foodie destination. This charming town has a variety of restaurants that offer everything from French pastries to farm-to-table cuisine. Here are twenty of the best restaurants in downtown Winter Garden that you won’t want to miss!

The 20 Best Winter Garden Restaurants 

Thai Blossom Restaurant

99 W. Plant Street // (407) 905-9917

Thai Blossom is a legend in Winter Garden, and I was thrilled to discover that they now offer lunch hours. Located on the same block as Scoops Ice Cream and The Chef’s Table at the Edgewater, the restaurant welcomes you with a spacious and inviting interior.

As I entered, I noticed the brown steam pipe-like apparatus overhead, perfectly matching the color scheme and adding a unique touch to the ambiance. The seating options include comfortable booths and four-top tables arranged in the center of the room, allowing for a relaxed and enjoyable dining experience.

Upon being seated, the friendly staff presented me with two menus—one with lunch specials and the other encompassing their entire selection. Asked for my drink order, I opted for water, and to my pleasant surprise, it was crystal clear and delicious. This small but significant detail showcased the restaurant’s attention to quality and ensured a refreshing start to my meal.

You see, while Florida’s tap water is potable, I don’t find it particularly palatable so the restaurants that serve delicious tasting water do so purposefully. For future visits, I made a mental note to try their specialty Thai Iced tea, described as “Thailand’s famous blend of slow-cooked bold teas combined with steamy milk.”

Fried wontons

With a plethora of appetizer choices, I chose the fried wontons from the lunch menu. Arriving on a plate, I was delighted to find eight thinly rolled sheets of delicious pastry enveloping savory ground chicken. The accompanying sweet and sour dipping sauce provided a perfectly balanced flavor combination that exceeded my expectations.

Additionally, as a thoughtful touch, the restaurant served a complimentary bowl of Tofu soup and a refreshing green salad with shredded carrots. The salad dressing, a sweet and light sauce, turned out to be a familiar favorite—Thai peanut dressing—which added a delightful twist to the salad.

Now, onto the main course—a challenging decision with the enticing options of chef specials, soups, and lunch specials. Thai Blossom offers a wide variety of authentic Thai dishes, ranging from teriyaki and pad thai to onion sauté and Thai basil. The menu allows you to customize your dish by choosing the preferred level of spice, from mild to Thai Hot.

Ultimately, I selected the garlic delight from the lunch specials, served traditionally with steamed vegetables such as mushrooms, broccoli, onion, carrots, and water chestnuts. The attentive staff accommodated my request to substitute celery for mushrooms and broccoli, ensuring a personalized and enjoyable dining experience. The seamless service was notable, with the servers promptly attending to any needs as they passed by.

For those with a heartier appetite, Thai Blossom’s Chef Specials offer an array of tantalizing options, including New Zealand steamed mussels, garlic mussel delight, mussels in green curry, param steamed chicken, salmon filet curry, and tofu lover’s delight.

I spoke with one gentleman reminiscing about his regular Friday night visits with his late wife, where they would indulge in the roasted duck curry and share a Florida Orange Sunshine Cake for dessert. It was heartwarming to hear how Thai Blossom holds cherished memories for its patrons. And that they have live music every Friday night.

roasted duck curry

With the extensive selection of dishes, Thai Blossom offers a variety of curry options, fried rice variations, seafood specials, and protein choices like chicken, vegetable, tofu, beef, pork, shrimp, or squid. The restaurant also features a well-curated selection of beer, red wine, and white wine to complement the dining experience.

To complete the culinary journey, Thai Blossom presents a tempting dessert menu. The options include the blossom banana delight, coconut delight (a half order of the banana delight served with coconut ice cream), the sunshine cake, an amazing chocolate cake, coconut ice cream with sticky rice or served alone, and lychee on ice. These delectable treats provide a sweet conclusion to a memorable meal.

Beyond the outstanding menu, what truly sets Thai Blossom apart is the atmosphere it cultivates. The happy hum of people engaged in conversations, the clinking of silverware on plates, and the contented sighs of diners all contribute to a rich and satisfying dining experience. It’s no wonder that once you’ve experienced Thai Blossom, you’ll find yourself longing to return, just as my friends and many locals had predicted.

Thai Blossom in Winter Garden encapsulates the essence of authentic Thai cuisine, providing a haven where delightful flavors, warm hospitality, and cherished memories come together in perfect harmony.

Come once and, like all my friends had told me who visit Thai Blossom Café in Winter Garden, you’ll want to return often.

The Chef’s Table at the Edgewater 

99 W Plant Street // (407) 230- 4837 

Divided into two multi-award-winning venues for two separate experiences, you will want to return multiple times to enjoy both The Chef’s Table and The Tasting Room. 

The Chef’s Table at the Edgewater, a fine dining restaurant located inside the historic Edgewater Hotel, The offers a seven-course tasting menu or three course dinner that changes daily based on the chef’s inspiration and the availability of ingredients. Diners sit at a communal table in the kitchen and watch as the chefs prepare each course, offering insights into the cooking techniques and flavor combinations.

The menu features classic dishes with modern twists, like crispy octopus with chorizo aioli and bacon-wrapped quail with cornbread stuffing. The decor is upscale and sophisticated, with dark wood paneling, velvet curtains, and sparkling chandeliers.

 pan-seared scallops

Favorite daughter enjoys my pan-seared scallops and I feast on the char-grilled filet with a parsnip puree in a sweet potato nest. For her entrée, she continues with the fish of the day, served with fresh morel mushrooms and asparagus risotto on an apple fennel salad. 


As usual, the desserts remain a source of delight with choice of a daily sorbet option, triple chocolate bread pudding, pistachio crème brulee, and chocolate dome cake with a dark chocolate bark and goat cheese frosting (I’d never heard of this before!).

The Tasting Room

99 W Plant Street // (407) 230- 4837 

The Tasting Room, an upscale wine bar and restaurant is a must-visit for oenophiles, with an extensive wine list featuring bottles from around the world. Offering a more casual dining experience than its upscale sister restaurant, the menu is focused on expertly crafted and beautifully presented small plates and shareable dishes, making it the perfect place for a leisurely evening of wine and conversation.

The menu features dishes like seared scallops, rock shrimp-chorizo ravioli, shell crab soup, braised pork chef tacos, duck fat fries, and artisanal cheese boards. If you plan to stay and chat (and you should!) consider the mini beef wellington trio which requires an additional 30 minutes to prepare. 

duck fat fries

Turn to dessert and enjoy the chocolate berry trifle or a strawberry and cream empanada. The chocolate berry trifle is one I’ll enjoy on return visits.

Chef’s Table at the Edgewater is run by Chef Kevin and Laurie Tarter, who also own The Tasting Room. The Tarters are committed to using fresh, locally sourced ingredients in their dishes, and they have built a reputation for creative, high-quality cuisine. The Tasting Room is a perfect example of their dedication to excellence, with a menu that changes frequently to showcase the best seasonal ingredients.

Rosallie Le French Café since 1983

141 W. Plant Street // (407) 347-5507

Rosallie Le French Café a charming, family-owned restaurant, a staple of the Winter Garden community for 40 years, brings a touch of Paris to Winter Garden with its authentic French pastries, delicious food, warm hospitality, and charming ambiance.

This cozy café with exposed brick interior and bistro chairs is renowned for its exquisite selection of freshly baked croissants, quiches, tarts, and macarons. Pair your favorite pastry with a perfectly brewed cup of coffee or a fragrant pot of loose-leaf tea for a delightful breakfast or afternoon treat.

The bakery also offers a range of cakes, tarts, and other desserts, all made in-house. Don’t be surprised when you return to the display counter for a treat for your ride home or whoever awaits you there.

charcuterie board

If you enjoy charcuterie boards, you’ll love The Country Plate. They’re happy to help you pair it with your favorite cab as you enjoy Italian Prosciutto, French Saucisson, Paris Ham, French Brie Cheese, French Comte, Homemade French Bread, and one of their famous tartes. 

Turn from the cashier to your left and find the serving counter with all your coffee accoutrements and peer back to the long tables that seat larger parties (be sure to make reservations if your family goes for brunch). The fresh flowers throughout the restaurant add depth and texture to the exposed brick. 

The café’s warm and inviting atmosphere makes it a perfect spot to relax and savor the flavors of France in the heart of Florida. Where happiness is homemade.

Market to Table

146 W Plant St // (407) 395-9871 

Market to Table, a farm-to-table restaurant located in the Roper Garden Building near the stage door of the Winter Garden Theatre, focuses on modern American cuisine with classic influences. Chef Ryan Freelove sources ingredients from local farms and artisanal producers to create a seasonal menu that showcases the best of Florida’s bounty. 

As you might expect, the menu changes frequently based on what’s in season, but you can always expect dishes that are creative, flavorful, and beautifully presented. 

Closed for lunch, reservations are suggested for the 3-course Prix Fixe Theatre Menu. Book no later than 6:00pm for a 7:30pm show.

Open Tuesday through Saturday nights, enjoy crafted cocktails with your dinner. Appetizers include shrimp cocktail, parmesan fries, truffle gnocchi, bone marrow, short rib ravioli, Spanish octopus, oysters, Prince Edward Island mussels, tempura battered fried squash blossom, and a mozzarella burrata.

I learned early to focus on one flavor profile or you can choose to have quite the gastronomic “party” with all that’s on offer.

Tempura battered fried squash blossom

While you’ll want to seriously consider the daily special, the proteins offered for the entrée helped me narrow my choice on appetizer. With a Big Board charcuterie, Lake Meadow Farm Chicken, red snapper, ricotta gnudi, braised short rib, seafood tower (favorite daughter’s choice), my eyes flew to the filet mignon with the potato puree.

The dessert menu reveals “The Cloud” the house made cotton candy I’ve seen in several Florida restaurants (but not in other states I’ve visited), sorbet tasting (four flavors), chocolate velvet cake, and carrot cake. 

When you choose the 3-course Prix Fixe Theatre Menu accompanied by a wonderful night at the Winter Garden Theatre (they have a bar ON STAGE you can enjoy before and after the show AND during intermission!), you’re all set for an amazing experience.

The Whole Enchilada

129 W Plant Street // (407) 347-9699

Enter The Whole Enchilada to discover a lively Mexican eatery that radiates friendliness and invites you to indulge in the vibrant flavors of Mexico in an atmosphere that instantly puts you at ease. Walk to the middle of the restaurant, to the left, to place your order from an inviting panel of options.

The cheerful décor creates an ambiance that feels like a friendly gathering of amigos. The open space with scatterings of booths and tables, infuses the space with a cozy, down-to-earth vibe.

The seating arrangements at The Whole Enchilada are designed to accommodate various preferences and group sizes. The mix of seating options creates an atmosphere that is convivial and relaxed, encouraging lively conversations and shared moments of enjoyment.

zesty tacos

The menu at The Whole Enchilada showcases the vibrant and bold flavors synonymous with Mexican cuisine. From zesty tacos and hearty burritos to their signature enchiladas, every dish is crafted with care and passion. Each bite is a tantalizing combination of spices, fresh ingredients, and homemade salsas that will transport your taste buds to the heart of Mexico.

So, whether you’re seeking a flavorful lunch or a festive dinner with friends, The Whole Enchilada offers a welcoming atmosphere that is both inviting and comfortable. Step inside, take a seat, and allow yourself to be enveloped in the lively ambiance and the irresistible aromas that fill the air. Prepare to embark on a culinary journey that celebrates the vibrant spirit of Mexican cuisine.

Crooked Can Brewing Company 

426 W Plant St #120 // (407) 395-9520

Crooked Can Brewing Company, an Orlando brewery and taproom in the Plant Street Market invites you to embark on a sensory journey through the artistry of craft beer. As you step in, prepare to be captivated by the symphony of aromas, flavors, and textures that await. Your senses will be engaged by the tantalizing scents wafting through the air. The harmonious blend of malt, hops, and yeast creates an olfactory masterpiece, stirring your anticipation for the exquisite brews that lie ahead. 

The Crooked Can brew masters are adept at blending old world techniques with cutting edge brewing practices. It’s the perfect place to take my nephew, an engineer in Seattle who has become quite the craft brew connoisseur. He can describe the fermentation process as well, I think, as our ancestor who was a cooper. He enjoys the fully body of what he describes as a “crisp” beer. Listening to my nephew and daughter speak about it allows me to enjoy the experience (I’m allergic to alcohol, so have this all on secondhand authority). 

They pointed out to me the option to use this facility for private events. The full menu catering, beverages, and entertainment options available (DJ? Dueling pianos?) in this lovely region with free parking and Wi-Fi make it a great option for groups up to 300.

The sight of gleaming brewing equipment creates a mesmerizing ambiance. It’s a testament to the craftsmanship that goes into each batch of beer produced on-site. The indoor and outdoor seating options offer a choice between cozy corners indoors or a refreshing breeze on the patio, allowing you to immerse yourself in the vibrant atmosphere of the brewery.

Crooked Can Brewing Company is more than just a place to savor exceptional beers; it’s a hub of entertainment and camaraderie. Live music fills the air, adding a rhythm to your experience and enhancing the lively ambiance. The brewery’s calendar brims with exciting events that bring together beer enthusiasts, fostering a sense of community and celebration.

Juicy burger

But let’s not forget the culinary delights that accompany the beers. The food options at the Plant Street Market with 20 vendors featuring natural, organic food with pizza, sushi, burgers, wings, or vegan complements the brews with a selection of pub favorites designed to satisfy every craving. Sink your teeth into juicy burgers, savor the succulent sandwiches, or indulge in the delectable flatbreads that burst with flavor. Each dish is thoughtfully prepared, featuring local ingredients that highlight the region’s culinary prowess.

As you sip on a pint of meticulously crafted beer, the flavors dance upon your palate, each sip revealing intricate layers of taste. From hop-forward IPAs to rich stouts and crisp lagers, the rotating selection of brews ensures there’s something to delight every beer connoisseur. The skilled brewers at Crooked Can are artisans, infusing their creations with passion and expertise, resulting in an exceptional drinking experience.

So, whether you’re a beer enthusiast, a food lover, or simply seeking a vibrant and inviting atmosphere, Crooked Can Brewing Company beckons you to join their spirited community. Immerse yourself in the symphony of flavors, revel in the camaraderie of fellow beer enthusiasts, and let your senses guide you on a remarkable journey through the world of craft beer.

The Attic Door

28 W Plant St (opens 4p) // (407) 750-7063

The Attic Door, a gastropub and wine bar offers evening entertainment with live music and a menu that features creative twists on pub classics, like green eggs n ham deviled egg (avocado and parmesan!), chicken que flatbread, sliders (meatball, pulled pork), or a blueberry smash burger (who knew blueberry jam would taste great on a burger? But it does!) 

Perfect for us with a big appetite, the blueberry smash burger for me with the flourless chocolate cake with whipped cream and berries for my “appetizer,” and for favorite daughter? The strawberry shortcake crème brulee, sizzling garlic shrimp (served with potatoes), and the bruschetta. When we come with a larger group, I think we’ll try the tasting tower. With three tiers of small bite appetizers, it’s a favorite amongst the crowd.


The wine list is extensive, with options from around the world, and they offer a range of craft beers. The outdoor patio is a great spot to enjoy a glass of wine or a craft beer as you watch the tourists and locals cruise along Winter Garden’s bustling historic district.

Opened in 2015, The Attic Door quickly became a popular spot for locals and visitors alike. Even with changes in management and ownership, the venue remains a local’s favorite as the owners continue to pride themselves on using high-quality ingredients, combined in new and interesting ways, in a laid-back atmosphere, 

The surprise to me? The afternoon tea experience. Offered about once a month, it sells out fast so watch the website and make reservations early. Featuring finger sandwiches, scones with clotted cream, desserts, and a pot of premium loose tea, expect to pay under $50 per person unless you add other alcoholic beverages. They offer special menus for children and have gluten free and vegetarian options available. Sorry, no vegan. They can provide the entire tea party to go, scheduled for 12:30p pick up with a current price of $160 to serve four. I can hardly wait to visit when it’s available.

The Winter Garden Pizza Company

42 W Plant Street // (407) 942-7282

Enter through the outdoor seating to the wafting smells of garlic knots baking and pizzas flying out the door with wide open, double storefront space with the second building for seating, it’s easy to see why so many people love coming back time after thyme. 

This casual pizzeria offers handmade, hand-tossed pies with generous toppings (everything you’d expect) and a bonus of a Plant Powered Pizza with three vegan toppings. The dough is made fresh daily, and the ingredients are sourced from local farms whenever possible. 

The decor is simple and unfussy, with an open kitchen and communal tables. Winter Garden Pizza is a local favorite when it comes to delicious pizzas in Winter Garden. But it’s so much more. They offer wonderful Italian dishes including baked ziti and chicken marsala, a classic spaghetti and fettucine alfredo. Feel like lasagna? They have it. Eggplant parmesan? My mother’s favorite, and they have it.

 Eggplant parmesan

You know our love for desserts … they offer cannoli and zeppolini. The latter are so tempting, Nonna Grace’s recipe for doughnuts tossed in cinnamon or powdered sugar, but it is possible to get a gluten free dough for the pizzas (just remember the cross contamination). 

In addition to fountain soda, they provide a selection of white and red wines, sangria, beer, and the house favorite: Sangue Di Guida. From Decordi, Italy, they tell us this translates to the “Blood of Judas” which is “sinfully delicious and contains crushed strawberry and cherries with a light effervescence.”

Winter Garden Pizza delivers flavorful combinations that keep customers coming back for more. With a casual and family-friendly atmosphere, it’s an excellent spot to indulge in a satisfying pizza feast.

The Hangry Bison

250 W Plant St // +14073479099

This delightful eatery takes pride in its commitment to locally sourced ingredients, ensuring a fresh and flavorful dining experience that will leave you craving for more.

As you step inside The Hangry Bison, you’ll be greeted by a rustic and cozy ambiance, adorned with open ceiling beams that exude a warm and welcoming atmosphere. The focal point of the space is the semicircular bar nestled in the front left corner, where skilled bartenders concoct tantalizing libations to complement your meal. But it’s the hostess you’ll meet first, always friendly, and helpful, especially for newbies looking for new experiences.

When it comes to the menu, The Hangry Bison truly shines with its delectable offerings. Their bison burgers take center stage, part of a build your own platform where other proteins could be chosen. Boasting juicy patties made from succulent, locally raised bison meat, each bite is a harmonious blend of rich flavors and satisfying textures that will have you savoring every mouthful.

But it’s not just the main dishes that steal the show at The Hangry Bison. Their appetizers are equally enticing, offering the perfect prelude to your meal. Indulge in the calamari & banana peppers, a delightful combination of crispy calamari paired with a subtle hint of heat from the peppers.

For a comforting treat, the pretzels & beer cheese are a match made in heaven, offering a satisfying blend of soft pretzels and creamy, savory cheese. And if you’re in need of comfort food, be sure to sample the Wisconsin cheese curds, crispy golden nuggets of cheesy goodness that are as addictive as they are delicious. They smell heavenly.

Bison burger

When it comes to their signature creations, “The House Hanghelds” steal the spotlight with their imaginative names and mouthwatering flavors. Sink your teeth into “The Doddzilla,” a towering masterpiece of a burger that combines bold flavors and hearty ingredients. Or opt for “The Trashley,” a tantalizing medley of flavors that will leave you craving more. And let’s not forget “The Hangry Red Head,” a fiery combination of spices and heat that is not for the faint of heart.

For those seeking a truly exceptional dining experience, The Hangry Bison offers featured meals that will leave you in awe. Sink your teeth into the Bison Striploin, a tender and flavorful cut of meat that highlights the unique qualities of bison. Or tantalize your taste buds with the Pineapple Bourbon Glazed Tuna, a harmonious blend of sweet and savory flavors that will transport you to culinary bliss.

In addition to their outstanding menu, The Hangry Bison also boasts a selection of libations that perfectly complement the flavors of their dishes. From craft beers to handcrafted cocktails, you’ll find the perfect beverage to enhance your dining experience.

So, whether you’re a carnivorous connoisseur seeking the perfect burger or an adventurous foodie eager to explore unique flavor combinations, The Hangry Bison in Winter Garden is a culinary haven that will satisfy your cravings and leave you delightfully satiated. Prepare to embark on a gastronomic journey where locally sourced ingredients, impeccable craftsmanship, and a cozy atmosphere converge to create a memorable dining experience.

Pammie’s Sammies (closed Sundays)

121 South Boyd Street // (407) 730-3212

This bright sandwich shop offers a selection of delicious sandwiches made with high-quality, thoughtfully sourced ingredients built to be “earth friendly and tastefully adventurous.” The menu features items such as chicken salad, roast beef, and smoked turkey, old family recipes from Pam’s childhood as well as new takes. 

The decor is warm, light, and inviting, with a casual and friendly atmosphere. If you call after hour, it’s Pam whose message you’ll hear – she’s set a great friendly tone for the visit. You can tell the entire team works from their heart and truly loves the dishes they serve. 

For me, the no-brainer choice is the BLT with the lettuce wrap. It amazes me how different this “simple” dish can taste. I appreciated that they provided large lettuce leaves that allowed me to eat without making too much of a mess. Eating with fork and knife just isn’t as fun. Paired with a side of sweet potato fries, I couldn’t even manage the dessert – which includes a gluten free cookie and “normal” cookies.

loaded tots

Next time, I want to try the loaded tots and maybe one of their salads. Their artful presentation makes it almost a shame to eat them. No wonder it’s one of the best Winter Garden restaurants.

Pilars Martini

146 West Plant Street Suite 120 // (407) 369-8900

Pilars Martini, a sophisticated lounge and a Winter Garden restaurants favorite amongst the Garden Theatre crowd, offers bar food ordered at the bar that’s tasty and can absolutely be your evening meal. Known for its handcrafted cocktails and extensive martini menu, this upscale establishment also offers a delectable selection of tapas and small plates or plates for the table.

Choose appetizers from parmesan fries, mozzarella burrata, fried calamari, seared scallops, shrimp cocktail, Spanish Octopus, Prince Edward Island Mussels, market burger, and chicken wings. Or order Cape Coe Oysters WiAnno by the dozen or half dozen.

The market or Caesar salad are always a great choice, but my loyalty remains with the iceberg wedge with tomatoes, applewood smoked bacon and ranch (blue cheese also available – and yes, blue, not bleu).

The menu is like Market to Table which makes me think Chef Ryan Freelove must be involved (it is!), but I’m grateful for the availability of these great dishes with live music. 

filet mignon with mash

It was tough to choose between the filet mignon and the fresh catch of the day, but the potato puree won out over the Israeli cous cous this day and the filet “won.’ Beautifully proportioned and cooked to my specifications, I look forward to having it again. 

The cozy and intimate ambiance, coupled with the impeccable service, creates an ideal setting for a memorable dining experience. It’s a 30s art deco décor surrounded, as you might expect with the Theatre association, surrounded by the arts. They’re well versed in catering to the pre-show and after theater parties – whether concert plays (like the recent Rock of Ages) or reunion tours and events.

Live music Thursday (open mic night) thru Sunday won’t interfere with your conversation, though you may be tempted to sit and listen. If you love jazz, be sure to make their Sunday Jazz Jam from 5 to 8 pm. They feature a remarkable variety of wonderful entertainers to extend your theatre going experience or enjoy a la carte.

The history of the name intrigued me. They say it originated in Spanish class at Lakeview High School, a nod to a youthful alter ego. If you have a playful alter ego, check it into Pilar’s and let us know how extraordinary your visit became!

Sweetland Cake & Tea

255 Tremaine Street // (407) 347-0060

Just one street off the main thoroughfare, Plant Street, on a Wednesday, Sweetland Cake & Tea is empty as I enter with an immediate smile. It’s like walking into a puffy pink pillow with your favorite scent and a feast for the eyes. From the sugar work displayed as wedding cakes in the display window to the cheeky lemon mousse in the display case (it’s a yellow lemon shaped mousse cake sitting on a brown base), it exemplifies everything sweet and happy.

It was the clapboard sign announcing “Brown Sugar Bubble Tea” that entices customers from the town’s fountain to Sweetland. The shop is empty when I visit on Wednesday after lunch, but bustling on the weekend, especially Saturdays when it’s so prominently on display with the Farmer’s Market across the street … 

An extensive menu of milk teas (favorite daughter chose the Brown Sugar Bubble Tea and the bubbles were still intact when I delivered it to her an hour later), fruit teas, freshly brewed teas, fruit smoothies, and blended teas, there’s a feast in liquid, solid, and semi-solid states. 

The young lady who helped me truly understood the inventory as I awaited my daughter’s response to text after sending photo after photo of the delicious treats in the display case. Would she like the lemon mousse? The walnut chocolate mousse decorated as a pink heart with a little walnut in the upper right hand corner? Or one of the decadent macarons (or 6 – buy 5 and you get one free).

For $2.50 each, that’s quite the bargain. Especially if you know all that is required to make macarons. It’s quite the complex process and you can see easily on display how all of these are baked with great love. 


If you’re still looking for options, their cookies and brownies are easily portable for you to continue your exploration of Winter Garden restaurants. But for any event, occasion, or just tonight’s dessert, take a good look at their Mousse Cakes, Chiffon Cakes, Mille Crepe Cakes, or New York style cheesecake. Ask what’s currently available because they frequently sell out – they are just that good. I think I’d have to start rationing my calories just to be able to enjoy all their sweets if I lived any closer. 

They advertise that they provide cakes for every occasion so I’m definitely going to keep them in the old rolodex. Their dedication is so complete, their goal to be more than delicious, to actually bring happiness and joy, they’ll even consult with you about the best options for your special event.

As Sweetland Cake & Tea says, “Let’s face it. A little bit of sugar makes everything better.” 

Apologies to the young lady who helped me. She is so lovely, and I’ve forgotten her name. She brought joy and happiness to my day!

Winter Garden Farmers Market

104 South Lakeview Avenue // +14076564155

Region renowned, Winter Garden hosts a vibrant Farmers Market every Saturday morning in the downtown area across from Sweetland Cake & Tea. Visitors can peruse the stalls filled with fresh produce, artisanal products, baked goods, and handmade crafts. I love walking amidst the stalls and choosing not only produce to take home for the week, but unusual combinations of items for a meal.

gluten free bagels

I might try a gluten free bagel from one vendor while my daughter enjoys the honey candies offered by another. The proteins are a little more thought provoking, so we frequent the vendors that have ready-made meals for that. The produce is easy, especially with fruit in season. You can make a meal of that alone and be supremely happy. Of course, the local smoothie operator is very popular. 

It’s an excellent opportunity to support local businesses, taste local flavors, and find unique souvenirs to take home. And keep in mind they’re taking sustainability seriously. No plastic bags, cups, straws, or utensils are available – biodegradable options are available. If you forget to bring a reusable bag, check at the Hospitality Tent for a complimentary recycle bag or purchase biodegradable bags from one of the vendors. Definitely one of the best Winter Garden restaurants.

The Downtown Deli

18 North Boyd Street // (407) 347-3873

I like their saying, “A BIT OF BETTER BUTTER MAKES A BETTER BATTER” and their breads are a great example of this.

Nestled in the heart of Winter Garden, on a side road that leads to the Centennial Fountain, this is one of the Winter Garden restaurants offering a charming and cozy setting that invites you to indulge in a delightful culinary experience perfect for the café, the outdoor seating, or a picnic in the park. As I stepped inside, the aroma of freshly brewed coffee from Piccolo Fine Coffees greeted me, creating a warm and inviting atmosphere. The deli showcases a diverse menu that caters to various tastes and preferences.

One standout item on the menu is the BBQ Jackfruit, a unique and flavorful vegan option that is sure to please even the most discerning palates. For those looking for a plant-based twist on a classic sandwich, the TLT (tempeh bacon, lettuce, tomato) provides a satisfying combination of smoky and fresh flavors. If you’re in the mood for a taste of France, the Croque Monsieur, with its layers of ham, cheese, and béchamel sauce, delivers a delightful indulgence.

Reuben Sandwich

The menu at The Downtown Deli also boasts a selection of beloved deli classics. The Reuben, a sandwich stacked with corned beef, sauerkraut, Swiss cheese, and Russian dressing, is a perennial favorite. The Pastrami, with its succulent slices of flavorful meat, is another option that tempts the taste buds. The Pulled Pork sandwich, featuring tender and tangy shredded pork, is a crowd-pleaser.

For those craving a touch of heat, the Buffalo Chicken sandwich offers a tantalizing combination of spicy chicken and cool, creamy dressing. And if you’re seeking a hearty option, the Roast Beef sandwich, with its tender slices of beef, is sure to satisfy.

To complement the sandwiches, The Downtown Deli offers a selection of daily soups, including Gazpacho and Tomato Basil. These homemade creations provide a comforting and nourishing accompaniment to your meal. On my visit, I couldn’t resist trying their house-made chicken salad with cranberries and a hint of onion, served with fresh lettuce on a flaky croissant. The combination of flavors and textures was simply divine—a true taste of culinary bliss. It’s rustic signs and friendly staff all add to the experience. Definitely one of the best Winter Garden restaurants.

NY Bagel Deli & Pizza

126 West Plant Street // (407) 993-6160

The Winter Garden NY Bagel Deli & Pizza (the owner has a branch in Celebration) is a haven for those seeking authentic New York-style bagels, deli fare, and delectable pizzas. As I entered, the sight of the extensive display cases filled with pastries, baked goods, and bagels was a testament to the bakery’s commitment to quality and tradition. Here’s why it’s one of the best Winter Garden restaurants.

While the array of choices was tempting, it was the lunch special that caught my attention when mentioned by the staff—a perfect combination of affordability and flavor. The “two slices and a drink” offer, priced at around $8 with tax, presented an enticing opportunity to sample their renowned pizzas.

Whether you prefer a thin crust or the Sicilian style, the pizza maker at NY Bagel Deli & Pizza skillfully crafts each pie to perfection. The cheese pizza I opted for was a mouthwatering blend of melted cheese and flavorful tomato sauce, while sipping on a refreshing Mountain Dew from their selection of Pepsi products.

cheese pizza

Aside from their delectable pizzas, NY Bagel Deli & Pizza offers a variety of other treats. From bagels of different flavors and textures to a wide range of deli classics, there’s something to satisfy every craving. The aroma of freshly baked goods wafts through the air, tempting patrons to explore the assortment of pastries and baked treats on display.

NY Bagel Deli & Pizza caters to both breakfast and lunch preferences, ensuring a delightful start to your day or a satisfying midday meal. Whether you’re in the mood for a traditional New York-style bagel with cream cheese or a hearty deli sandwich bursting with flavorful ingredients, this establishment has you covered. It’s definitely one of the best Winter Garden restaurants.

Mangoni Italian Market Pizza

251 Tremaine Street

Walking through the doors of Mangoni Italian Market Pizza, you’ll be struck by the inviting ambiance that seamlessly blends elegance and comfort. No wonder it’s one of the best Winter Garden restaurants. And I finally grasp “Atelier Dining.” The interior exudes a cozy charm, with warm lighting, tasteful decor, and a welcoming atmosphere. Despite its cafeteria-style ordering system, the restaurant manages to create a refined setting where guests can enjoy their meals. Staff explain, Jonathan Pluvinet, Italian parentage but born in the South of France, created a European dining experience here in Winter Garden to infuse that food culture into our American lifestyle.

They describe their philosophy as “Product, Service, Atmosphere,” and can fulfill it with the first stop … the gelato food cart on the corner. While it wasn’t open mid-day Wednesday, I’d bet that it does a booming business each Saturday when the Farmer’s Market across the street brings crowds. 

At Mangoni Italian Market Pizza, the ordering process is part of the fun. As you enter through the front door, you’ll be greeted by a tantalizing display of toppings and ingredients, allowing you to create a pizza tailored to your preferences. This interactive experience adds an element of excitement to your meal, as you handpick the ingredients that will ultimately compose your perfect pizza.

Witness how fresh and natural the ingredients are, compiled while you watch, walk along the display cases to choose.  Once you’ve selected your desired toppings, you can choose to dine indoors or outdoors. 

Seating areas vary from high top bar stools to low slung couches with sufficient tables for your plates and glasses. It’s practical for socialization while being utterly functional, allowing you to enjoy wonderful food in a relaxed atmosphere.

When it comes to their pizzas, Mangoni Italian Market Pizza goes above and beyond to ensure an exceptional culinary experience. They pride themselves on crafting their own dough in-house, using pure Italian olive oil. The dough is carefully prepared and allowed to rise for a generous 24 hours, resulting in a light and airy crust with a perfect balance of texture and flavor.

The commitment to quality extends to their tomato sauce as well. Mangoni Italian Market Pizza takes great care in making their own tomato sauce from scratch, using the finest ingredients sourced from local farms and importing authentic Italian tomatoes. The sauce is free from additives or artificial flavors, allowing the natural sweetness and tanginess of the tomatoes to shine through in every bite.

Margherita pizza

One of the standout dishes is their classic Margherita pizza, which embodies the simplicity and traditional flavors of Italian cuisine. Topped with fresh basil, mozzarella cheese, and tomato sauce, this pizza is a testament to the beauty of minimalism.

If you’re looking for a burst of flavors, the Quattro Formaggi pizza is a must-try. This indulgent creation features a blend of four cheeses, typically including mozzarella, gorgonzola, Parmesan, and fontina. The combination of these rich and creamy cheeses creates a symphony of flavors that will leave you craving more.

For those with a penchant for meaty delights, the Mangoni Special pizza is a popular choice with a variety of savory meats, pepperoni, sausage, and bacon, and a medley of vegetables for a hearty pizza experience.

garlic knots

Aside from their signature pizzas, Mangoni Italian Market Pizza offers a selection of appetizers and sides to complement your meal. From fresh salads to savory garlic knots and indulgent desserts, there’s something for every palate.

Once you’ve made your selections from the enticing menu, the culinary team at Mangoni Italian Market Pizza will take your chosen pizza and expertly bake it in their imported Italian wood-fired pizza oven. The oven, fueled by locally sourced oak wood, imparts a distinct smoky flavor, and imparts a delightful char to the crust, elevating the taste and authenticity of the pizza.

But Mangoni Italian Market Pizza offers more than just pizzas. Their menu also includes a variety of tantalizing options to satisfy every palate. Indulge in charcuterie boards, featuring a selection of premium cured meats, artisan cheeses, and accompanying accouterments that create a delightful harmony of flavors. If you’re in the mood for something lighter, their fresh salads are a perfect choice, combining crisp greens, vibrant vegetables, and delicious dressings.

homemade cannoli

To complete your meal on a sweet note, Mangoni Italian Market Pizza offers a tempting selection of homemade cannoli and other desserts. Sink your teeth into these delectable treats, filled with creamy, sweet fillings that are sure to hit the spot and leave you with a satisfied smile.

Whether you’re seeking a taste of Italy, a personalized pizza experience, or simply a delightful meal in an elegant yet relaxed environment, Mangoni Italian Market Pizza is the place to be. With its rich history, inviting atmosphere, and mouthwatering dishes, it’s no wonder that locals and visitors alike flock to this culinary gem in Winter Garden.

Make note, Wednesday nights at Mangoni Italian Market Pizza hold a special treat for the ladies. It’s Ladies’ Night, a time when women can gather with friends and enjoy a delightful evening of good food, great company, and perhaps even some exclusive offers or discounts. 

At Mangoni Italian Market Pizza, the combination of their homemade dough, flavorful sauces, locally sourced ingredients, and dedication to authentic Italian cooking techniques creates a dining experience that is as genuine as it is delicious. With the added convenience of a gelato cart, Ladies’ Night, and an inviting atmosphere, this culinary destination amongst the Winter Garden restaurants is a must-visit for pizza enthusiasts and Italian cuisine lovers alike.

Urban on Plant Kitchen and Bar

132 West Plant Street // (407) 614-2765

Urban on Plant, a vibrant and contemporary find amongst the Winter Garden restaurants, exudes a country chic vibe as you step inside. The interior design features a harmonious blend of distressed wood paneling and artistic touches including decorated guitars, and an open kitchen creating a trendy yet comfortable ambiance.

The food at Urban on Plant Kitchen and Bar is equally impressive, with a menu that showcases a fusion of flavors and creative culinary techniques. The restaurant focuses on serving plant-based dishes, catering to those seeking vegetarian, vegan, and gluten-free options. However, even non-vegetarians will find an array of enticing choices that are sure to satisfy their taste buds.

Watermelon Arugula Salad

Start your dining experience with an appetizer like their crispy Brussels sprouts, which are perfectly roasted and seasoned. The menu offers a variety of creative salads bursting with freshness and unique combinations of ingredients. From the zesty Southwest Quinoa Salad to the refreshing Watermelon Arugula Salad, these vibrant dishes are a testament to the restaurant’s commitment to delivering both flavor and nutrition.

For the main course, Urban on Plant Kitchen and Bar offers a diverse selection of plant-based dishes that are both visually stunning and delicious. Their innovative approach to vegetarian and vegan cuisine ensures that every dish is crafted with care and attention to detail. Whether you choose their flavorful Portobello Mushroom Steak, hearty Black Bean Burger, or aromatic Thai Curry Bowl, each bite will be a delightful journey of flavors and textures.

Ready to splurge? Try the stuffed potato dip (their take on potato skins) or pretzel bites.

Want an upscale image of comfort food? Try the mushroom mac n’ cheese.

For healthy and tasty, go for the edamame. It’s always a top choice for me. 

A friend enjoys the Teriyaki Salmon Spring Rolls and Shakshuka. It’s enough for a meal. But the soups and salads call.


For me, the French Dip was the obvious choice, though the fresh fish tacos are on the list for my next visit. Hold the provolone and the French Dip met all the qualities of a great meal.

Complementing the delectable food, Urban on Plant Kitchen and Bar boasts a well-curated bar that offers a variety of handcrafted cocktails, refreshing mocktails, and a thoughtful selection of wines and craft beers. The bar team is skilled at creating unique and enticing drink options that perfectly complement the plant-based cuisine and enhance your overall dining experience.

What sets Urban on Plant Kitchen and Bar apart is their commitment to sustainability and locally sourced ingredients. They strive to work with local farmers and suppliers, ensuring that their ingredients are fresh, high-quality, and environmentally friendly. This dedication to sustainability adds an extra layer of value to the dining experience, allowing guests to indulge in flavorful meals while supporting ethical and eco-conscious practices.

Whether you’re a dedicated vegetarian, a health-conscious food lover, or simply someone looking to explore innovative and delicious plant-based cuisine, Urban on Plant Kitchen and Bar is the perfect destination. With its trendy atmosphere, inventive menu, and commitment to sustainability, this restaurant offers a dining experience that is both memorable and satisfying for all. Definitely one of the best Winter Garden restaurants.

Harrell’s Hot Dogs and Cold Cones

54 West Plant Street // (407) 554-2021

Harrell’s Hot Dogs and Cold Cones, serving up delicious hot dogs since 2020, offers street window and indoor seating. As you approach the humble eatery, you’ll immediately notice the inviting aroma of sizzling hot dogs wafting through the air, drawing you in with its irresistible scent if the outside window is too packed with customers.

Walk up or step inside, and you’ll find no-frills, black painted walls with a neon sign “Hot ity dog” that adds to the charm of the place. The atmosphere is lively, bustling with locals and visitors alike enjoying their favorite hot dog creations. The friendly and welcoming staff will greet you with a smile, ready to guide you through the menu and help you build your perfect hot dog.

Grilled hot dog with mustard and relish

One of the highlights of Harrell’s Hot Dogs is the option to build your own dog. This customizable experience allows you to create a hot dog masterpiece tailored to your exact preferences. From traditional toppings like ketchup, mustard, and relish to more adventurous choices like sauerkraut, jalapenos, and chili, the possibilities are endless. This freedom to mix and match toppings ensures that every bite is exactly how you like it.

On this day, the classic dog was chosen on a classic bun, with relish and scallions, with an additional charge for bacon. This take away order remained delicious according to favorite daughter even an hour later.

Three Birds Cafe

2 West Plant Street // (407) 614-1010

Three Birds Cafe is a delightful and inviting spot amongst the Winter Garden restaurants that attracts a vibrant crowd, including millennials looking for a bright, open space to work while enjoying delicious food. As you enter the cafe, you’ll immediately notice the airy atmosphere, creating a sense of spaciousness and comfort. The interior design features a modern aesthetic with exposed brick walls that add a touch of rustic charm.

The friendly and knowledgeable young women behind the counter assist you in navigating the menu and catering to any dietary preferences or restrictions you may have. Whether you’re vegan, gluten-free, or simply seeking healthy options, Three Birds Cafe has you covered. They take pride in offering a variety of dishes that cater to different dietary needs without compromising on flavor or quality.

One of the highlights of Three Birds Cafe is their all-day brunch menu which allows you to indulge in your favorite breakfast items at any time of the day. With vegan, gluten-free, and healthy options available, you can enjoy a scrumptious and satisfying meal that aligns with your dietary choices. From classic brunch fare like avocado toast and pancakes to more unique creations, there’s something to please every palate.

Grilled Cheese with Tomato bisque

If you’re in the mood for a comforting and elevated experience, the grilled cheese paired with their tomato bisque is a must-try. The combination of melted cheese and the rich, flavorful bisque takes this classic sandwich to new heights. Another popular choice is their chicken salad, which incorporates the delightful combination of pecans and cranberries. You even have the option to add grapes or apples for an extra burst of freshness.

Aside from their brunch offerings, Three Birds Cafe offers a variety of sandwiches to satisfy your lunchtime cravings. Whether you opt for the club turkey sandwich or the spicy chicken avocado, each bite is a delightful explosion of flavors and textures. To accompany your meal, you can indulge in their “That’s What Cheese Said” artisanal board, featuring a selection of cheeses that pairs perfectly with their beer, wine, or coffee. If you’re not in the mood for an alcoholic beverage, their specialty non-alcoholic options like sunrise juice and minted hibiscus tea are refreshing choices.

club turkey sandwich

Three Birds Cafe beckons you with its warm and inviting embrace. Step into a haven of tranquility where the sun bathes the space in a gentle glow, casting a vibrant aura upon the surroundings. The atmosphere is alive with the buzz of conversation and the clinking of cups, creating a symphony of connection and camaraderie.

While you revel in the culinary delights, the air is alive with the hum of productivity and connection. Three Birds Cafe is a gathering place for the community, a sanctuary for both solitude and camaraderie. With shared Wi-Fi and ample space, it becomes a haven for creatives and professionals alike, fostering an environment where ideas flourish and collaboration blooms.

As you sip on your artisanal coffee or specialty non-alcoholic beverage, time seems to slow down. Engage in conversation with friends, old and new, as you share stories and laughter. It’s a place where connections are forged, and memories are made. The vibrant energy of Three Birds Cafe sparks inspiration and rejuvenation, making it the perfect spot to refuel both body and mind.

So, whether you seek a moment of solitude to immerse yourself in your thoughts or a vibrant space to connect with kindred spirits, Three Birds Cafe welcomes you with open arms. Let the bright and airy ambiance, friendly service, and delectable menu transport you to a place of comfort and joy. Step into a world where delicious food, genuine connections, and inspired moments intertwine, leaving you with a lasting impression and a desire to return time and time again. Definitely one of the best Winter Garden restaurants.

Bonus #21 – A Staple Amongst The Winter Garden Restaurants

Scoops Ice Cream

99 West Plant Street // (407) 656-3369

Scoops Ice Cream is a beloved destination amongst the Winter Garden restaurants, situated between The Edgewater and Thai Blossom Restaurant. As you approach the shop, you’ll immediately notice the long line of eager customers that often stretches down the block. The anticipation builds as people patiently wait to indulge in the delectable treats that Scoops has to offer.

The atmosphere around the store window at Scoops is lively and vibrant, with an air of excitement in the crowd as they wait in the specially created black link serpentine path created in front. Friendly staff behind the counter are always ready with a smile, assisting customers in choosing from their enticing array of ice cream flavors.

Scoops Ice Cream prides itself on its wide selection of flavors, catering to every palate and preference. From classic choices like chocolate, vanilla, and strawberry to more unique and innovative creations, or old standby favorites like cherry vanilla, raspberry, and pistachio. There is something to satisfy every ice cream lover. 

pistachio ice cream

Whether you’re in the mood for a creamy indulgence, a fruity sorbet, or even a dairy-free option, Scoops has you covered. Whether you opt for a simple cone, waffle cone, or cup, or a decadent banana split piled high with toppings, every bite is a delightful taste sensation. 

Scoops Ice Cream has become a cherished spot in Winter Garden, attracting locals and visitors alike. It’s not just about the ice cream itself, but also the experience of being part of a community of ice cream enthusiasts. Standing in line, chatting with fellow customers, and sharing the excitement of choosing flavors and toppings creates a sense of camaraderie and anticipation.

So, when you find yourself in Winter Garden on a warm day or simply craving a sweet treat, join the line at Scoops Ice Cream. Indulge in their delicious ice cream creations, embrace the joyous atmosphere, and join the countless others who have fallen in love with the delightful flavors that Scoops has to offer.

Winter Garden, Florida, has no shortage of great restaurants, from classic French cuisine to plant-based eats and everything in between. Each of these Winter Garden restaurants offers a unique dining experience, with its own decor, menu, and atmosphere. Whether you’re looking for a cozy gastropub, a health-conscious eatery, or an elegant fine dining experience, Winter Garden has something to offer.

Winter Garden Restaurants Wrap Up

The best Winter Garden restaurants indeed epitomize Florida’s vibrant culinary culture. These eateries showcase an incredible variety, from local seafood delicacies to internationally inspired cuisine. Combining top-tier service, innovative menus, and a charming ambience, they contribute significantly to the region’s gastronomic reputation.

The commitment to quality and sustainability makes the best Winter Garden restaurants a must-visit for both locals and tourists. In conclusion, they make dining in Winter Garden an unforgettable experience, highlighting the city as a coveted destination for food enthusiasts.

Visiting other destinations in Florida? Check out our other guides:

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