Winter Park Holiday Events

Holiday events Happening Next in Winter Park, FL

Community Shred Event (and Toy & Food Drive)

 Nelson Financial Planning 4 Dec 2025
TOY-DRIVES FREE

The Best Christmas Pageant Ever

 Shaeffer Hall at St. John Church 12 Dec 2025
CHRISTMAS

Holiday Classic Mini Session (SOLD OUT)

 Hannibal Square 8 Nov 2025
HOLIDAY

Pre Black Friday Flash Sale

 2828 Casa Aloma Way suite 300 7 Nov 2025
BLACK-FRIDAY FREE

Mix & Mingle: A Jewelry Social

 Penthouse 450 13 Nov 2025
HOLIDAY FREE

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

Fiddler’s Welcomes Back Willy & The Pour Boys

 Fiddler's Green Irish Pub & Eatery 30 Nov 2025
WORKSHOPS

Yule Be Sorry You Asked

 Shaeffer Hall at St. John Church 13 Dec 2025
ART

GROWvember Fall Plant Sale

 Mead Botanical Garden 7 Nov 2025
KIDS FREE

Vegan Thanksgivng Potluck- Winter Park

 Shady Park 22 Nov 2025
FOOD-DRINKS

Christmas Minis

 Lake Baldwin Park 8 Nov 2025
CHRISTMAS

Tinker Time

 721 W New England Ave 16 Nov 2025
MEETUPS FREE

USBC Orlando Regional presents Baby DJ Holiday Toy Drive

 Aloma Bowling Center 6 Dec 2025
TOY-DRIVES

Christmas on The Avenue (ONE SPOT)

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

Christmas on The Avenue (SOLD OUT)

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

EXHIBITION TOUR | Portrait of a Movement: A New Approach to the Bloomsbury Group

 Rollins Museum of Art 14 Nov 2025
ART

CFBAA Holiday Party 2025!

 Ravenous Pig 10 Dec 2025
HOLIDAY

Holiday Boat Parade Paddle & Toy Drive

 Dinky Dock Park 13 Dec 2025
UGLY-CHRISTMAS-SWEATER-DAY USD 34 TO 61

Holiday Showcase & Mini-Match Winter Park Ballroom with Adj. Larry Dean

 6904 Aloma Ave, Winter Park, FL 32792-7003, United States 6 Dec 2025
HOLIDAY

Thanksgiving Harvest Celebration Brunch Buffet at The Alfond Inn

 The Alfond Inn at Rollins College 27 Nov 2025
BRUNCH USD 0 TO 159

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
CHRISTMAS

Kwiat | Fred Leighton Holiday Trunk Show

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

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

 Center for Health & Wellbeing 5 Nov 2025
HOLIDAY

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