Winter Park Christmas Events

Community Shred Event (and Toy & Food Drive)

Nelson Financial Planning 4 Dec 2025

Happy Hour Tour at The Alfond Inn / November

The Alfond Inn at Rollins College 5 Nov 2025

"At the Square" Mini Sessions

Winter Park Florida 12 Oct 2025

The Best Christmas Pageant Ever

Shaeffer Hall at St. John Church 12 Dec 2025

Greyhaven

Conduit 21 Nov 2025

Emo Night Karaoke

Conduit 6 Nov 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

Happy Hour Tour at The Alfond Inn / December

The Alfond Inn at Rollins College 3 Dec 2025

Fast Fashion - The Depeche Mode Experience & Burn - The Cure Experience

Aloma Cinema Grill 4 Oct 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

Ulcerate

Conduit 5 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

A Classic Christmas

Knowles Memorial Chapel 13 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

Royal Graves

Conduit 3 Dec 2025