Winter Park Christmas Events

Community Shred Event (and Toy & Food Drive)

Nelson Financial Planning 4 Dec 2025

Candlelight: Christmas Carols on Strings - Orlando

1300 S Denning Dr, Winter Park, FL 11 Dec 2025

Christmas Swing Dance

6904 Aloma Ave, Winter Park, FL 32792-7003, United States 13 Dec 2025

The Best Christmas Pageant Ever

Shaeffer Hall at St. John Church 12 Dec 2025

Holiday Classic Mini Session (SOLD OUT)

Hannibal Square 8 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

Yule Be Sorry You Asked

Shaeffer Hall at St. John Church 13 Dec 2025

Happy Hour Tour at The Alfond Inn / November

The Alfond Inn at Rollins College 5 Nov 2025

Christmas Minis

Lake Baldwin Park 8 Nov 2025

Christmas on The Avenue (ONE SPOT)

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

Annual San Pedro Center Christmas Celebration!

95 Bishop Grady Lane, Winter Park, FL, United States, Florida 32792 17 Dec 2025

Christmas on The Avenue (SOLD OUT)

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

Auditions: A Politically Incorrect Christmas

6900 Aloma Avenue , Winter Park, FL, United States, Florida 32792 9 Nov 2025

Happy Hour Tour at The Alfond Inn / December

The Alfond Inn at Rollins College 3 Dec 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

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