Winter Park Holiday Events

52nd Annual Autumn Art Festival

Central Park In Winter Park, Florida 11 Oct 2025

Community Shred Event (and Toy & Food Drive)

Nelson Financial Planning 4 Dec 2025

GROWvember Fall Plant Sale

Mead Botanical Garden 7 Nov 2025

The Best Christmas Pageant Ever

Shaeffer Hall at St. John Church 12 Dec 2025

USBC Orlando Regional presents Baby DJ Holiday Toy Drive

Aloma Bowling Center 6 Dec 2025

A Christmas Romance Tour with Marcus Anderson & Rebecca Jade

460 E. New England Ave., Winter Park, FL, United States, Florida 32789 19 Dec 2025

Annie Jr. Registration Information

6900 Aloma Avenue , Winter Park, FL, United States, Florida 32792 4 Oct 2025

Yule Be Sorry You Asked

Shaeffer Hall at St. John Church 13 Dec 2025

Vegan Thanksgivng Potluck- Winter Park

Shady Park 22 Nov 2025

Christmas on The Avenue (SOLD OUT)

402 Welborne Ave, Winter Park, FL 32789-4216, United States 23 Nov 2025

Holiday Classic Mini Session (SOLD OUT)

Hannibal Square 8 Nov 2025

Christmas on The Avenue (SOLD OUT)

402 Welborne Ave, Winter Park, FL 32789-4216, United States 22 Nov 2025

Fairy Hair Fun at the Commons CO-OP Local Market ~ Winter Park

Center for Health & Wellbeing 5 Nov 2025

A Classic Christmas

Knowles Memorial Chapel 13 Dec 2025

Christmas on The Avenue (SOLD OUT)

402 Welborne Ave, Winter Park, FL 32789-4216, United States 30 Nov 2025

Kwiat | Fred Leighton Holiday Trunk Show

152 South Park Avenue, Winter Park, FL, United States, Florida 32789 12 Dec 2025

Season’s Greetings from the Garden

Mead Botanical Garden, Winter Park 14 Dec 2025

Roberto Coin Trunk Show

152 South Park Avenue, Winter Park, FL, United States, Florida 32789 4 Dec 2025

5th Annual Kid$ Bi$ Children's Business Fair Orlando, Florida

150 N New York Ave Winter Park, FL 32789, USA 13 Dec 2025

Parking Revocation

Conduit 13 Nov 2025