Winter Park Christmas Events

Twelve Sips of Christmas — Holiday Cocktail Making Class

The Alfond Inn at Rollins College 15 Dec 2026

A Magical Brunch with Santa at The Alfond Inn

The Alfond Inn at Rollins College 13 Dec 2026

Florida Blue's Winter Wonderland - FREE Toy Giveaway

Florida Blue Center - Orlando 4 Dec 2026

Candlelight: Christmas Classics

Orlando Museum of Art 18 Dec 2026

Chanukah on the Park

Winter Park Central Park 5 Dec 2026

Candlelight - Christmas Classics at The Azalea Lodge at Mead Gardens

The Azalea Lodge at Mead Gardens 17 Dec 2026

Holiday Eggnog & Ugly Sweaters

The Alfond Inn at Rollins College 19 Dec 2026

Adam Hawley | December 12 | Blue Bamboo

460 E. New England Ave., Winter Park, FL, United States, Florida 32789 12 Dec 2026

Candlelight: Christmas Classics

Azalea Lodge at Mead Garden 17 Dec 2026

Wreaths & Wine — Holiday Wreath-Making Workshop

The Alfond Inn at Rollins College 17 Dec 2026

Groove Sleighers Christmas Show | November 28 | Blue Bamboo

460 E. New England Ave., Winter Park, FL, United States, Florida 32789 28 Nov 2026

Vivacity Presents: A Vintage Christmas | December 5 | Blue Bamboo

Blue Bamboo Center For The Arts 5 Dec 2026

Gingerbread at The Alfond Inn

The Alfond Inn at Rollins College 20 Dec 2026

Holiday Pie Making Class with Executive Chef Antwan Ellis

The Alfond Inn at Rollins College 21 Dec 2026

A Very Merry Wine Tasting

The Alfond Inn at Rollins College 22 Dec 2026

Orlando Jazz Orchestra Holiday Show | December 6 | Blue Bamboo

Blue Bamboo Center For The Arts 6 Dec 2026

Meet The Grinch @ Foxtail Coffee (Winter Park) FREE EVENT!

1282 N Orange Ave, Winter Park, FL 32789 24 Dec 2026

Merry Mornings & Coffee: A Tasting Experience with Artifx Cafe Coffee

The Alfond Inn at Rollins College 18 Dec 2026

Rifle Paper Co. Holiday Sidewalk Sale

558 W New England Ave. No. 150 Winter Park, FL 32789 2 Nov 2026

Season's Blendings: A Holiday Aromatherapy Workshop with Terra Vitae

Winter Park Yoga 14 Nov 2026

Holiday Boat Parade Paddle & Toy Drive

Dinky Dock Park 12 Dec 2026

Meet The Grinch @ Foxtail Coffee (Howell Branch) FREE EVENT!

2451 Howell Market Ln #1105, Winter Park, FL 32792 28 Nov 2026

A Christmas Carol the Musical

Trinity Prep Auditorium 18 Dec 2026

Free Movie for Seniors: Hershey

Aloma Cinema Grill 7 Dec 2026

Candlelight: Christmas Carols on Strings

Orlando Museum of Art 18 Dec 2026

Wonderland Gift Shoppes

5525 Tangerine Ave 20 Nov 2026

Free Stage Production: A Christmas Survival Guide

The Winter Park Playhouse 9 Dec 2026

Girl The PARK Day!🎄| FREE EVENT!

Blue Jacket Park 29 Nov 2026

Romance Book Club: The Nightmare Before Kissmas Book Bedazzling

Writer's Block Bookstore 9 Dec 2026

2026 San Pedro Center Christmas Celebration!

95 Bishop Grady Lane, Winter Park, FL, United States, Florida 32792 16 Dec 2026

Auditions: Another Politically Incorrect Christmas

6900 Aloma Avenue , Winter Park, FL, United States, Florida 32792 8 Nov 2026

LYS Glow Golf Scramble / Christmas Party

Winter Park Golf Course 17 Dec 2026

Winter Park Romance & Roses Hunt

251 S Park Ave 6 Sep 2026

6th Annual Kid$ Bi$ Children Business Fair

150 N New York Ave, Winter Park, FL 32789-3116, United States 19 Dec 2026

Candlelight: Christmas Classics

Mead Botanical Garden 17 Dec 2026

Pretty Pity (HOMETOWN HOLIDAY SHOW), No One Road, Moonstone, Almost Mine, and Zozingbo

Conduit 11 Dec 2026

Silent Night

Center for Health & Wellbeing 10 Dec 2026

Yuletide Jane Austen Ball

The Woman's Club of Winter Park 11 Dec 2026

The Buzzcatz Holly Jolly Christmas

Blue Bamboo Center For The Arts 11 Dec 2026