Winter Park Holiday Events
Holiday events Happening Next in Winter Park, FL
52nd Annual Autumn Art Festival
Central Park In Winter Park, Florida
11 Oct 2025
FESTIVALS
Community Shred Event (and Toy & Food Drive)
Nelson Financial Planning
4 Dec 2025
TOY-DRIVES
FREE
GROWvember Fall Plant Sale
Mead Botanical Garden
7 Nov 2025
KIDS
FREE
The Best Christmas Pageant Ever
Shaeffer Hall at St. John Church
12 Dec 2025
KIDS
USBC Orlando Regional presents Baby DJ Holiday Toy Drive
Aloma Bowling Center
6 Dec 2025
TOY-DRIVES
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
Annie Jr. Registration Information
6900 Aloma Avenue , Winter Park, FL, United States, Florida 32792
4 Oct 2025
ART
Yule Be Sorry You Asked
Shaeffer Hall at St. John Church
13 Dec 2025
ART
Vegan Thanksgivng Potluck- Winter Park
Shady Park
22 Nov 2025
FOOD-DRINKS
Christmas on The Avenue (SOLD OUT)
402 Welborne Ave, Winter Park, FL 32789-4216, United States
23 Nov 2025
HOLIDAY
Holiday Classic Mini Session (SOLD OUT)
Hannibal Square
8 Nov 2025
HOLIDAY
Christmas on The Avenue (SOLD OUT)
402 Welborne Ave, Winter Park, FL 32789-4216, United States
22 Nov 2025
HOLIDAY
Fairy Hair Fun at the Commons CO-OP Local Market ~ Winter Park
Center for Health & Wellbeing
5 Nov 2025
HOLIDAY
A Classic Christmas
Knowles Memorial Chapel
13 Dec 2025
ENTERTAINMENT
Christmas on The Avenue (SOLD OUT)
402 Welborne Ave, Winter Park, FL 32789-4216, United States
30 Nov 2025
HOLIDAY
Kwiat | Fred Leighton Holiday Trunk Show
152 South Park Avenue, Winter Park, FL, United States, Florida 32789
12 Dec 2025
HOLIDAY
Season’s Greetings from the Garden
Mead Botanical Garden, Winter Park
14 Dec 2025
MUSIC
Roberto Coin Trunk Show
152 South Park Avenue, Winter Park, FL, United States, Florida 32789
4 Dec 2025
HOLIDAY
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
TRIPS-ADVENTURES
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Winter Park Events
Winter Park Holiday Events