Winter Park Holiday Events

The Art of Thanksgiving: Holiday Dining at The Alfond Inn

The Alfond Inn at Rollins College 26 Nov 2026

Thanksgiving To-Go: Take-Home Holiday Dinners from The Alfond Inn

The Alfond Inn at Rollins College 25 Nov 2026

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

Candlelight: Christmas Classics

Orlando Museum of Art 18 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

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

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

Boards & Bottles: Build Your Own Charcuterie Board & Wine Tasting

The Alfond Inn at Rollins College 16 Dec 2026

A Christmas Carol the Musical

Trinity Prep Auditorium 18 Dec 2026

Girl The PARK Day!🎄| FREE EVENT!

Blue Jacket Park 29 Nov 2026

The Trio Returns To Imperial On Park!

The Imperial On Park 5 Dec 2026

Orlando Philharmonic Orchestra Presents: Holiday Pops in Winter Park

Central Park in Winter Park 251 South Park Avenue Winter Park , FL 32789 6 Dec 2026

A Winter Seduction feat. Julian Vaughn & Marcus Anderson with Special Guest Lori Williams

Blue Bamboo Center For The Arts 19 Dec 2026

Thanksgiving Gratitude Flow

Winter Park Yoga 26 Nov 2026

Kelly/Scott Jazztet: Artfully Christmas | December 27 | Blue Bamboo

Blue Bamboo Center For The Arts 27 Dec 2026

Winter Park Romance & Roses Hunt

251 S Park Ave 6 Sep 2026

ReachConf 2026 featuring CGDC Collab

1815 FL-436 5 Nov 2026

Silent Night

Center for Health & Wellbeing 10 Dec 2026

Evan Taylor, Adrian Crutchfield & Holiday Delights

Blue Bamboo Center For The Arts 20 Dec 2026

Landau Eugine Murphy JR | December 5 | Blue Bamboo

Blue Bamboo Center For The Arts 5 Dec 2026

10th Annual Holiday Bridge Tournament (Canasta & Mahjong, too!)

Interlachen Country Club (2245 Interlachen Court, Winter Park, FL 32792) 4 Dec 2026