Winter Park Holiday Events

Holiday events Happening Next in Winter Park, FL

Winter Parktoberfest - 2nd Annual Winter Park Oktoberfest

 Mead Botanical Garden 6 Sep 2025
MUSIC USD 18 TO 225

Community Shred Event (and Toy & Food Drive)

 Nelson Financial Planning 4 Dec 2025
TOY-DRIVES FREE

Family Weekend - God the Master Builder

 5410 Lake Howell Rd, Winter Park, FL, United States, Florida 32792 22 Aug 2025
WORKSHOPS

52nd Annual Autumn Art Festival

 Central Park In Winter Park, Florida 11 Oct 2025
FESTIVALS

Hot In Herre: 2000s Dance Party

 Conduit 19 Sep 2025
PARTIES

Holiday Classic Mini Session

 Hannibal Square 8 Nov 2025
HOLIDAY

A Classic Christmas

 Knowles Memorial Chapel 13 Dec 2025
ENTERTAINMENT

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

The Best Christmas Pageant Ever

 Shaeffer Hall at St. John Church 12 Dec 2025
KIDS

Yule Be Sorry You Asked

 Shaeffer Hall at St. John Church 13 Dec 2025
ART

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