Winter Park Festivals Events

Chanukah on the Park

Winter Park Central Park 5 Dec 2026

Hannibal Square Food & Music Fest

Hannibal Square 19 Nov 2026

Michael Andrew & Ray Gelato | November 20 | Blue Bamboo

Blue Bamboo Center For The Arts 20 Nov 2026

The Jury Experience – The Deadly Boat Ride

Orlando Museum of Art 20 Dec 2026

Healthy Harvest Fall Festival

Florida Blue Center - Orlando 14 Nov 2026

3rd Annual Fall Fest Networking Event

4Rivers Smokehouse 10 Nov 2026

Taste of Winter Park

Winter Park Farmers' Market Venue 20 Jan 2027

25th Annual Unity Heritage Festival

Winter Park Community Center 17 Jan 2027

Winter Park Art Festival

Park Avenue, Winter Park 12 Mar 2027

FCC 2026 Fall Festival

1720 Howell Branch Rd, Winter Park, FL, United States, Florida 32789 21 Nov 2026

A Winter Seduction feat. Julian Vaughn & Marcus Anderson with Special Guest Lori Williams

Blue Bamboo Center For The Arts 19 Dec 2026

Orlando Renaissance Faire

Southport Community Park 3505 E Landstreet Orlando FL, 32827 6 Dec 2026

Kelly/Scott Jazztet: Artfully Christmas | December 27 | Blue Bamboo

Blue Bamboo Center For The Arts 27 Dec 2026

Rollins College Piano Academy 2027

Rollins College 12 Feb 2027

The 68th Winter Park Sidewalk Art Festival

Park Avenue, Winter Park 19 Mar 2027

House Band @ The Winter Park Autumn Arts Festival

Central Park In Winter Park, Florida 15 Nov 2026

Season’s Greetings from the Garden

Mead Botanical Garden 20 Dec 2026