Winter Park Holiday Events
Holiday events Happening Next in Winter Park, FL
Free Movie for Seniors: Downton Abbey: Grand Finale
Aloma Cinema Grill
16 Sep 2025
ENTERTAINMENT
FREE
Free Movie for Seniors: Downton Abbey: Grand Finale
Aloma Cinema Grill
18 Sep 2025
ENTERTAINMENT
FREE
Women’s Social Club Dip Into Fall Signature Experience (Winter Park)
Peterbrooke Chocolatier of Winter Park
13 Sep 2025
FOOD-DRINKS
USD 69
Sip & Shop - Fall Finds and Local Vibes
1300 S Denning Dr
28 Sep 2025
SHOPPING
USD 15
Community Shred Event (and Toy & Food Drive)
Nelson Financial Planning
4 Dec 2025
TOY-DRIVES
FREE
52nd Annual Autumn Art Festival
Central Park In Winter Park, Florida
11 Oct 2025
FESTIVALS
USBC Orlando Regional presents Baby DJ Holiday Toy Drive
Aloma Bowling Center
6 Dec 2025
TOY-DRIVES
Vegan Thanksgivng Potluck- Winter Park
Shady Park
22 Nov 2025
FOOD-DRINKS
Shofar Service on Park Ave!
The University Club of Winter Park
23 Sep 2025
HOLIDAY
The Best Christmas Pageant Ever
Shaeffer Hall at St. John Church
12 Dec 2025
KIDS
Holiday Classic Mini Session (SOLD OUT)
Hannibal Square
8 Nov 2025
HOLIDAY
A Christmas Romance Tour with Marcus Anderson & Rebecca Jade
460 E. New England Ave., Winter Park, FL, United States, Florida 32789
19 Dec 2025
MUSIC
Fairy Hair Fun at the Commons CO-OP Local Market ~ Winter Park
Center for Health & Wellbeing
5 Nov 2025
HOLIDAY
Roberto Coin Trunk Show
152 South Park Avenue, Winter Park, FL, United States, Florida 32789
4 Dec 2025
HOLIDAY
Yule Be Sorry You Asked
Shaeffer Hall at St. John Church
13 Dec 2025
ART
A Classic Christmas
Knowles Memorial Chapel
13 Dec 2025
ENTERTAINMENT
Season’s Greetings from the Garden
Mead Botanical Garden, Winter Park
14 Dec 2025
MUSIC
5th Annual Kid$ Bi$ Children's Business Fair Orlando, Florida
150 N New York Ave Winter Park, FL 32789, USA
13 Dec 2025
FESTIVALS
Parking Revocation
Conduit
13 Nov 2025
CONTESTS
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Winter Park Events
Winter Park Holiday Events