Live music on the plaza every Friday night, a free festival at the farmers market on Nov. 7 and a handmade market by local makers 50 and older on Nov. 14.
Quick Facts
- Fridays on the Plaza: Every Friday, 7–9 p.m., Centennial Plaza Gazebo
- Health & Harvest Festival: Saturday, Nov. 7, 8 a.m.–1 p.m., Winter Garden Farmers Market
- Craft Affair: Saturday, Nov. 14, 10 a.m.–2 p.m., Jessie Brock Community Center
- Cost: Free to attend all three
Fridays on the Plaza
The City of Winter Garden puts on a free concert at the Centennial Plaza Gazebo in Historic Downtown every Friday from 7 to 9 p.m. The November lineup:
- Nov. 6: Sammy Valez (rock)
- Nov. 13: MalCan’tHearYou (indie rock)
- Nov. 20: Dale New (classic rock)
- Nov. 27: Lucky to Be (acoustic)
On Dec. 4, the plaza hands the night over to Light Up Winter Garden.
Health & Harvest Festival, Nov. 7
The Saturday farmers market gets a fall upgrade on Nov. 7. Healthy West Orange hosts a free Health & Harvest Festival there with the city from 8 a.m. to 1 p.m., with games, giveaways, fitness classes, cooking lessons and health screenings.
The Winter Garden Farmers Market itself sets up every Saturday from 8 a.m. to 1 p.m. at the Downtown Pavilion, with more than 100 vendors. Leashed dogs and cats are welcome, and the three-level parking garage at 160 S. Boyd St. is free.
Craft Affair, Nov. 14
The city’s Craft Affair fills the Jessie Brock Community Center from 10 a.m. to 2 p.m. on Nov. 14. Everything for sale is handmade by members of Winter Garden’s Active 50+ community, from seasonal décor and jewelry to artwork and gifts, just in time for holiday shopping. Admission is free.
Still exploring West Orange? The city’s new botanical garden and wellness park at Tucker Ranch is open, and our Nov. 5–8 weekend guide covers the rest of the county.
Why We’re Hyped
That’s every Friday night in November plus two Saturdays, all free and all in Winter Garden. The Friday concerts and the harvest festival are both in Historic Downtown, so either one pairs easily with dinner on Plant Street.
The Details
- Fridays on the Plaza: Fridays, 7–9 p.m. (Dec. 4 is Light Up Winter Garden instead) · Centennial Plaza Gazebo, Historic Downtown Winter Garden · Free · Schedule
- Health & Harvest Festival: Saturday, Nov. 7, 8 a.m.–1 p.m. · Downtown Pavilion, 104 S. Lakeview Ave., Winter Garden, FL 34787 · Free · Event page
- Craft Affair: Saturday, Nov. 14, 10 a.m.–2 p.m. · Jessie Brock Community Center, 310 N. Dillard St., Winter Garden, FL 34787 · Free · Event page
- Farmers market parking: Free garage at 160 S. Boyd St.
- City of Winter Garden: 407-656-4111 · City events calendar
