Fall Festivals in Winter Park

Check out happening fall festivals events all around Winter Park, FL

Women’s Social Club Dip Into Fall Signature Experience (Winter Park)

Sat, 13 Sep at 11:00 am Peterbrooke Chocolatier of Winter Park USD 69

Sip & Shop - Fall Finds and Local Vibes

Sun, 28 Sep at 11:00 am 1300 S Denning Dr USD 15

52nd Annual Autumn Art Festival

Sat, 11 Oct at 09:00 am Central Park In Winter Park, Florida

Free for Seniors: Swing Into September Dance

Wed, 10 Sep at 03:00 pm Winter Park Community Center Free

Chalk a Masterpiece - Fall Into Art 2025

Sat, 01 Nov at 09:00 am Central Park In Winter Park, Florida