5 Things to Do in Winter Garden, Florida

The city of Orlando doesn’t need an introduction. The Theme Park Capital of the World draws in visitors from all over the world. But did you know that less than 30 minutes away from the hustle and bustle of Walt Disney World lies the quaint town of Winter Garden, FL, a charming community set on the shores of Lake Apopka? 

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Winter Garden is home to a number of great restaurants, shops and boasts an exciting arts scene, and lots of historical and natural charm. Its proximity to theme parks makes it a destination worth visiting for both residents and travellers.

For us, the appeal of Winter Garden was the West Orange Trail, one of the top bike trails in Florida. But there is so much more to Winter Garden than that – from the historic Downtown Winter Garden area, the Garden Theatre, and the city’s museums to markets, restaurants and shops. 

If you are wondering if you should visit the city of Winter Garden on your next trip to the Orlando area, let’s dive into it! Here are our recommendations for things to do in Winter Garden, Florida!

How to Get to Winter Garden

By Car 

From Orlando

Orlando is the closest major city to Winter Garden. It’s 30 minutes west of Downtown Orlando, with the drive taking 20 minutes via FL-408 W and covering 26.07km (16.2mi). It’s also 30 minutes north of theme parks like Walt Disney World (12.87 km or 8 mi) and Universal Orlando Resort (24 km or 15 mi). 

From Winter Park

It’s a 30-minute drive via FL-408W, covering 35.24 km (21.9 mi).

From The Villages

It’s a 50-minute drive via Florida’s Turnpike, covering 71.78 km (44.6 mi).

From Tampa

It’s a 1hr 20min drive on the I-4E, covering 133.58 km (83 mi).

From Gainesville

It’s a 1hr 35min drive via I-75S and Florida’s Turnpike, covering 158.68 km (98.6 mi).

From Jacksonville

It’s a 2hr 16min dive via I-95 S, covering 247 km (153.5 mi)

From Fort Myers

It’s a 3-hour drive via Highway 17 N, covering 265.22 km (164.8mi)

From Miami

It’s a 3hr 30-min drive via Florida’s Turnpike, covering 388 km (241.4mi).

By Plane

The closest international airports to Winter Garden are in Orlando, and there are two of them:

Orlando International Airport (MCO)

Orlando International Airport offers the most flights to multiple destinations than any other airport in Florida. It’s 31km (19.3mi) away from Winter Garden, and the drive takes about 30 minutes.

Orlando Sanford International Airport (SFB)

This airport is the smaller of the two and is about 45 minutes away from Winter Garden, or about 41km (25.5mi).

If you’re flying in from Canada, like we did, there are daily flights from Toronto, Montreal, Vancouver, Ottawa and Calgary. 

Airplane passing by

Best Time to Visit Winter Garden 

The temperature in Winter Garden ranges from 10°C (51°F) to 32°C (90°F) and rarely falls below 3°C (38°F) or above 34°C (94°F). It’s hot and rainy from May until October. This coincides with the Atlantic hurricane season which peaks between mid-August and mid-October. The best weather is from November until March, when it’s mild and cool. 

Florida is one of the top destinations for domestic travel in the mainland USA, and Orlando’s theme parks make it a must-visit for families and teenagers. Peak season for tourists falls during school holidays, such as spring break in March and April and summer from June to September.

The best time to visit is from November until March. The weather is moderate, and there are fewer showers throughout these months, ideal for outdoor adventures. Plus, students will be in school by then, so you’ll see fewer crowds compared to other times of the year.

That said, Winter Garden hosts events year-round, so chances are there’s something to check out in town whenever you go. 

Winter Garden, Florida
Winter Garden, Florida

Things to Do in Winter Garden, FL

1. Explore West Orange Trail

Operating from sunrise until sunset, the West Orange Trail is a 22-mile network that starts at Killarney Station, cuts through the downtown area, and ends along Rock Springs Road in Apopka. It is a beautiful trail, paved and wide with lots of tree coverage, perfect for a day out, even on a hot summer day. The trail is also part of the multi-use Florida Coast to Coast Trail, which spans the Gulf of Mexico to the Atlantic Ocean. 

We chose to explore the trail on bikes from West Orange Trail Bikes & Blades, located right on the trail. Rates start at USD $15/hour. It was the perfect spot to park our car, hop on a bike and head into town on 2 wheels. 

Exploring downtown on bikes was easy as the trail runs right into Plant St at the heart of the city. It was easy to lock up our bikes while we checked out markets, had lunch and explored the town. It was the perfect day out!

West Orange Trail, Winter Garden
West Orange Trail, Winter Garden
things to do in winter garden fl
Oksana, while biking through the West Orange Trail
things to do in winter garden fl
Max riding a bike on the West Orange Trail

READ NEXT: 13 Best Bike Trails in Florida (Our Recommendations)

2. Visit the Winter Garden Heritage Museum 

The Winter Garden Heritage Museum is stop worth making in town! The museum has an extensive collection of historical artifacts dating back to the pioneer days. It also has rotating exhibits on the rich history of West Orange County. The caboose outside, along with the 1950s fire truck, and vintage tractors are a big hit with the kids… and kids at heart!

Admission is free. The Heritage Museum is open Thursdays through Saturdays from 11 a.m. to 3 p.m.

If you have time, check out the nearby Central Florida Railroad Museum with extensive stories from Florida’s railroad pioneers. There is lots of railroad memorabilia inside and the staff are kind and full of enthusiasm for all things railroad. Another must for kids or curious adults. 

Not into history but enjoy art? Pop into the SOBO Art Gallery or Studio by the Winter Garden Art Association for a glimpse of local art. 

Heritage Museum, Winter Garden
Heritage Museum, Winter Garden

3. Winter Garden Farmers Market

Located in the Downtown Pavilion, the famous Winter Garden Farmers Market opens every Saturday morning from 8am to 1pm.

You’ll find over 100 local vendors and small businesses selling everything from local produce to handmade products, delicious meals, fresh flowers, and more. There’s even free live music as you stroll through the market, courtesy of local musicians.

THe market is one of the best we’ve visited in Florida (and beyond). There are lots of unique and interesting handicrafts, great food stalls and entertainment. If you find yourself in Orlando area on a Saturday, trust us, this market is worth the detour to Winter Garden!

Farmer's Market, Winter Garden
Farmer’s Market, Winter Garden
Farmer's Market, Winter Garden
Farmer’s Market, Winter Garden

4. Explore the Market at Plant Street, Winter Garden

Plant Street Market is another local community market in downtown Winter Garden. There are about 20 vendors in one big building offering natural, organic foods and handmade goods. There are lots of spots to grab a bite, a drink, or a cuppa. 

At the end of the market is the award-winning Crooked Can Brewing Company, known for its craft beer. 

Plant Street Market, Winter Garden
Plant Street Market, Winter Garden

5. Shop and Dine at the Winter Garden Village 

The historic Downtown Winter Garden has the city’s own premiere shopping district. You can find many shopping and dining options at the Winter Garden Village at Fowlers Grove.

Other Things to Do Nearby 

Hike the Tibet-Butler Preserve

This preserve with over 3.6 miles of easy hiking trails is green oasis in Orlando area. It’s only 20 mins from Winter Garden and is worth a visit if you are looking for another spot to stretch your legs on a trail that’s suitable for the whole family. 

The preserve loops through a longleaf pine forest and scrub, a bayhead swamp, and a cypress-linked lakeshore. 

Max at Tibet-Butler Preserve, things to do in winter garden fl
Max at Tibet-Butler Preserve
Tibet-Butler Preserve, Winter Garden
At the Tibet-Butler Preserve, Winter Garden
Tibet-Butler Preserve, Winter Garden
Oksana at Tibet-Butler Preserve, Winter Garden

Where to Eat: Best Restaurants in Winter Garden, FL

Market to Table

Head here for Modern American cuisine with a unique seasonal menu. We had a delicious meal that included scallops, short ribs, prosciutto-wrapped burrata, and bone marrow. Save room for the “cloud” desert.

Oksana in Market to Table Restaurant, where to eat in Winter Garden
Oksana in Market to Table Restaurant
Market to Table Restaurant
Market to Table Restaurant

Plant St. Market

Plant Street Market offers a wide variety of food, from BBQ, mac and cheese, sushi, ceviche, and deli items from the Butcher Shop. It’s a great place to come when you just can’t agree on where to go – there are options here for everyone! The local brewery, Crooked Can Brewing Company, is also a must-try for beer enthusiasts.

Plant Street Market, Winter Garden
Plant Street Market, Winter Garden

Urban on Plant Kitchen & Bar

This is another well-rated restaurant inspired by American and world cuisine and cocktails, and it is made with fresh and locally sourced ingredients. Best-sellers include fresh fish tacos, bacon and egg flatbread, and bone-in pork chop. Vegetarian and gluten-free options are also available.

Where to Stay in Winter Garden, FL

Edgewater Hotel

Edgewater Hotel has been in operation for over 90 years. It is a local landmark and an authentic historic hotel. Guests can experience the original 1927 ambience and historic architecture but with modern comfort.

The rooms are air-conditioned and come with private bathrooms, memory foam bedding, and flat-screen TVs. Plus, they have 3 on-site restaurants. While we didn’t stay there, we popped in during our time in Winter Garden. This spot feels like an institution, and raving reviews confirm that it’s a great choice for anyone looking to stay in the heart of Winter Garden. 

Edgewater Hotel, where to stay in Winter Garden
Edgewater Hotel, Winter Garden
Edgewater Hotel, Winter Garden
Edgewater Hotel, Winter Garden

ette Hotel

During our visit to the area, we stayed at the new ette Hotel. Though located in Kissimmee and not in Winter Garden, this stylish 5-star hotel with 126 rooms and suites is worth a mention. 

The hotel is beautiful and elegantly furnished. The rooms are spacious and tastefully furnished and offer all the modern amenities you’d expect in a hotel of this calibre. 

The hotel has a full-service spa for facials and wellness treatments, an outdoor swimming pool, a fitness centre, a luxury goods store, a book room, a laundry museum (the first of its kind!), plus a herb garden courtyard.

The on-site restaurant, Salt & Cellar by Akira Back offers a taste of Akira’s exquisite cuisine with Asian inspired dishes and cocktails that are out of this world! The restaurant also serves afternoon high tea with little sandwiches, madeleines, and scones which we really enjoyed!

USA Florida Orlando Ette hotel 6704920
Our room at the Ette Hotel

The Bottom Line

Winter Garden is a hidden gem in the Orlando area and a destination worth visiting in Florida. From cycling the West Orange Trail, learning more about local history at Downtown Winter Garden, and enjoying the many dining options, visitors of all ages will find a different kind of adventure in this small town.


Disclaimer: Our visit to Winter Garden was provided courtesy of Visit Orlando and Visit Florida. But as always, all opinions expressed in this article are our own, no matter who is footing the bill. 

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