Winter Garden is the kind of town where you park once and stay all day. Historic downtown is all brick buildings on Plant and Main streets, with the paved West Orange Trail running right down the middle. Grab a coffee, walk the trail, and see where the day takes you.
Photo: Freeholdman12 via Wikimedia Commons, CC BY 4.0
Best things to do in Winter Garden
Saturday at the Winter Garden Farmers Market. This is the big one. It runs every Saturday, all year, from 8 AM to 1 PM at the Downtown Pavilion, 104 S. Lakeview Ave. More than 100 vendors set up, and live music starts at 9 AM. Leashed dogs are welcome, and parking is free in the garage at 160 S. Boyd St.
A show at the Garden Theatre. This 1935 theater at 160 W. Plant St. has a Spanish courtyard look and a dark blue ceiling full of stars. It hosts plays, concerts and classic movie nights.
A walk or bike ride on the West Orange Trail. Start downtown or at Killarney Station, 17914 State Road 438. The trail is open sunrise to sunset.
Free museums downtown. The Winter Garden Heritage Museum at 1 N. Main St. and the Central Florida Railroad Museum at 101 S. Boyd St. are both free and great for a rainy afternoon.
Where to eat in Winter Garden
Downtown is packed with places to eat. Plant Street Market is a food hall in the middle of it all, with 20 local vendors under one roof, open seven days a week.
On a budget? Daniel's Cheesesteak House on East Plant Street and Perrotti's NY Deli are two of our go-to cheap eats. For Italian, Cariera's Fresh Italian on Dillard Street has an "Under $20" menu. See more in our Cheap Eats guide.
Seasonal events in Winter Garden
The holidays are when Winter Garden really shows off. Light Up Winter Garden is Friday, Dec. 4, from 6 to 9 PM at City Hall, 300 W. Plant St., and it is free. The next morning brings the Winter Garden Christmas Parade at 10 AM. On select nights in December, City Hall turns into A Merry Winter Garden Light Show set to music.
Santa also visits the farmers market on Dec. 12 and Dec. 19. Find every date in our free Holiday Guide.
More from West Orange Bite
Free guides: This Weekend, Farmers Markets, Free Things to Do, Best Brunch, Holiday Guide, Cheap Eats, Hidden Gems.
Towns: Windermere, Ocoee, Horizon West.
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