A Magical Brunch with Santa at The Alfond Inn Sun, 13 Dec at 10:00 am The Alfond Inn at Rollins College USD 0 TO 76 HOLIDAY
Florida Blue's Winter Wonderland - FREE Toy Giveaway Fri, 04 Dec at 05:00 pm Florida Blue Center - Orlando FREE CHRISTMAS
Candlelight - Christmas Classics at The Azalea Lodge at Mead Gardens Thu, 17 Dec at 08:45 pm The Azalea Lodge at Mead Gardens CANDLELIGHT-CONCERTS
Twelve Sips of Christmas — Holiday Cocktail Making Class Tue, 15 Dec at 05:30 pm The Alfond Inn at Rollins College USD 64 HOLIDAY
Holiday Eggnog & Ugly Sweaters Sat, 19 Dec at 03:30 pm The Alfond Inn at Rollins College USD 32 FITNESS
Candlelight: Christmas Classics Fri, 18 Dec at 06:00 pm Orlando Museum of Art USD 44 TO 90 CANDLELIGHT-CONCERTS
Wreaths & Wine — Holiday Wreath-Making Workshop Thu, 17 Dec at 05:30 pm The Alfond Inn at Rollins College USD 87 HOLIDAY
Holiday Pie Making Class with Executive Chef Antwan Ellis Mon, 21 Dec at 05:30 pm The Alfond Inn at Rollins College USD 224 HOLIDAY
Adam Hawley | December 12 | Blue Bamboo Sat, 12 Dec at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 MUSIC
Candlelight: Christmas Classics Thu, 17 Dec at 06:30 pm Azalea Lodge at Mead Garden USD 46 TO 112 CANDLELIGHT-CONCERTS
Gingerbread at The Alfond Inn Sun, 20 Dec at 03:00 pm The Alfond Inn at Rollins College USD 47 FITNESS
Groove Sleighers Christmas Show | November 28 | Blue Bamboo Sat, 28 Nov at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 CHRISTMAS
Rifle Paper Co. Holiday Sidewalk Sale Mon, 02 Nov at 10:00 am 558 W New England Ave. No. 150 Winter Park, FL 32789
Vivacity Presents: A Vintage Christmas | December 5 | Blue Bamboo Sat, 05 Dec at 03:00 pm Blue Bamboo Center For The Arts MUSIC
Merry Mornings & Coffee: A Tasting Experience with Artifx Cafe Coffee Fri, 18 Dec at 09:00 am The Alfond Inn at Rollins College USD 29 FITNESS
Orlando Jazz Orchestra Holiday Show | December 6 | Blue Bamboo Sun, 06 Dec at 03:00 pm Blue Bamboo Center For The Arts MUSIC
Season's Blendings: A Holiday Aromatherapy Workshop with Terra Vitae Sat, 14 Nov at 12:00 pm Winter Park Yoga USD 48 HOLIDAY
Candlelight: Christmas Carols on Strings Fri, 18 Dec at 08:30 pm Orlando Museum of Art USD 42 TO 83 CANDLELIGHT-CONCERTS
Romance Book Club: The Nightmare Before Kissmas Book Bedazzling Wed, 09 Dec at 06:15 pm Writer's Block Bookstore USD 8 TO 30 FITNESS
2026 San Pedro Center Christmas Celebration! Wed, 16 Dec at 06:00 pm 95 Bishop Grady Lane, Winter Park, FL, United States, Florida 32792 MUSIC
Auditions: Another Politically Incorrect Christmas Sun, 08 Nov at 05:30 pm 6900 Aloma Avenue , Winter Park, FL, United States, Florida 32792 ART
6th Annual Kid$ Bi$ Children Business Fair Sat, 19 Dec at 10:00 am 150 N New York Ave, Winter Park, FL 32789-3116, United States BUSINESS
Pretty Pity (HOMETOWN HOLIDAY SHOW), No One Road, Moonstone, Almost Mine, and Zozingbo Fri, 11 Dec at 07:00 pm Conduit USD 20 MUSIC