Candlelight: Mozart vs. Beethoven Fri, 09 Oct at 06:00 pm Orlando Museum of Art USD 36 TO 91 ENTERTAINMENT
Candlelight: Tribute to Pink Fri, 09 Oct at 08:30 pm Orlando Museum of Art USD 36 TO 59 CANDLELIGHT-CONCERTS
Candlelight: The Best of Joe Hisaishi Sat, 17 Oct at 06:30 pm Azalea Lodge at Mead Garden USD 67 TO 97 ENTERTAINMENT
The Jury Experience – The Deadly Boat Ride Sat, 10 Oct at 04:30 pm Orlando Museum of Art USD 44 TO 77 ART
Candlelight: Queen vs. ABBA | Orlando Fri, 16 Oct Azalea Lodge at Mead Botanical Garden CANDLELIGHT-CONCERTS
Candlelight: Tribute to Queen Fri, 06 Nov at 08:30 pm Orlando Museum of Art USD 33 TO 85 CANDLELIGHT-CONCERTS
Cigano Swing | October 23 | Blue Bamboo Fri, 23 Oct at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 MUSIC
Candlelight: Tribute to Taylor Swift Thu, 19 Nov at 06:30 pm Orlando Museum of Art USD 36 TO 71 CANDLELIGHT-CONCERTS
Candlelight: Vivaldi's Four Seasons Thu, 19 Nov at 08:45 pm Orlando Museum of Art USD 51 TO 83 CANDLELIGHT-CONCERTS
Boards & Bottles: Build Your Own Charcuterie Board & Wine Tasting Wed, 04 Nov at 07:00 pm The Alfond Inn at Rollins College USD 133 FOOD-DRINKS
48 Hour Film Project Orlando Best of Screening & Awards Sat, 17 Oct at 06:00 pm Aloma Cinema Grill USD 16 FITNESS
Backyard Biodiversity Day Native Plant Sale Sat, 24 Oct at 09:00 am Mead Botanical Garden FREE FITNESS
Winter Park Wine and Dine (Holiday Party) Wed, 02 Dec at 05:30 pm Winter Park Farmers' Market Venue USD 61 TO 362 FITNESS
The Art of Thanksgiving: Holiday Dining at The Alfond Inn Thu, 26 Nov at 10:30 am The Alfond Inn at Rollins College USD 0 TO 161 THANKSGIVING
Callisto Sextet with Jeremy Fratti | October 9 | Blue Bamboo Fri, 09 Oct at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 MUSIC
Annual Longwood Luau Sat, 07 Nov at 04:00 pm 3592 Aloma Ave Suite 2, Winter Park, FL, United States, Florida 32792 ART
Walter Parks & The Unlawful Assembly | October 16 | Blue Bamboo Fri, 16 Oct at 08:00 pm Blue Bamboo Center For The Arts MUSIC
Candlelight: Christmas Classics Fri, 18 Dec at 06:00 pm Orlando Museum of Art USD 38 TO 80 CANDLELIGHT-CONCERTS
Maitland Symphony Orchestra with Washington Garcia | October 25 | Blue Bamboo Sun, 25 Oct at 03:00 pm Blue Bamboo Center For The Arts MUSIC
Pink-a-Tude Reloaded Soiree’ de Gala of Hope | Breast Cancer Awareness Gala Sat, 24 Oct at 05:00 pm Winter Park Community Center USD 0 TO 642 NONPROFIT
Stand Up Winter Park: James Yon & Absar Siddiqui | October 10 | Blue Bamboo Sat, 10 Oct at 08:00 pm Blue Bamboo Center For The Arts COMEDY
Ricky & The Buzzcatz: A Holly Jolly Christmas | December 11 | Blue Bamboo Fri, 11 Dec at 08:00 pm Blue Bamboo Center For The Arts HOLIDAY
Assel Jean-Pierre | November 7 | Blue Bamboo Sat, 07 Nov at 08:00 pm Blue Bamboo Center For The Arts MUSIC
2026 PRSA Orlando Chapter Awards Gala & Annual Meeting Thu, 05 Nov at 06:00 pm Rice Family Pavilion USD 80 TO 105 MEETUPS
Free Concert: Neil Diamond Tribute Show Mon, 02 Nov at 03:00 pm Winter Park Community Center FREE CONCERTS
Candlelight: Tribute to Dolly Parton Sun, 27 Dec at 08:30 pm Orlando Museum of Art USD 42 TO 84 ENTERTAINMENT
Ultimate Santana Tribute Band | November 14 | Blue Bamboo Sat, 14 Nov at 08:00 pm Blue Bamboo Center For The Arts MUSIC
Allan Vache Swingtet | November 1 | Blue Bamboo Sun, 01 Nov at 03:00 pm Blue Bamboo Center For The Arts MUSIC
Candlelight: Christmas Classics Thu, 17 Dec at 06:30 pm Azalea Lodge at Mead Garden USD 46 TO 102 CANDLELIGHT-CONCERTS
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
Winter Park Murder Mystery: Solve the case! Sun, 01 Nov at 12:00 am Peacock Fountain USD 10 TRIPS-ADVENTURES
Stage to Screen | November 6 | Blue Bamboo Fri, 06 Nov at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 CONCERTS
Michael Andrew & Ray Gelato | November 20 | Blue Bamboo Fri, 20 Nov at 08:00 pm Blue Bamboo Center For The Arts MUSIC
Candlelight: Tributo a Juan Luis Guerra Sat, 26 Dec at 08:30 pm Orlando Museum of Art USD 42 TO 84 ENTERTAINMENT
Candlelight: Featuring Vivaldi’s Four Seasons Fri, 08 Jan at 06:15 pm Azalea Lodge at Mead Garden USD 47 TO 82 ENTERTAINMENT
FREE Horror Trivia (Halloween Horror Nights Edition) Tue, 20 Oct at 07:00 pm Conduit FREE MISCELLANEOUS
25th Annual Unity Heritage Festival Sun, 17 Jan at 01:00 pm Winter Park Community Center FREE FESTIVALS
THE WALTEN FILES: Fan-Made Live-Action Series | Episode 1: "Pilot" Sat, 17 Oct at 06:00 pm Aloma Cinema Grill USD 5 TO 100 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
Free Movie for Seniors: Lucy Shimmers and the Prince of Peace Mon, 19 Oct at 12:00 pm Aloma Cinema Grill FREE FITNESS
The Porch in Winter Park, Florida - Doc Probes - Beach & Buffett Thu, 12 Nov at 05:30 pm The Porch Winter Park PARTIES
Vivacity Presents: A Vintage Christmas | December 5 | Blue Bamboo Sat, 05 Dec at 03:00 pm Blue Bamboo Center For The Arts MUSIC
Palm Beach Society Orchestra | November 29 | Blue Bamboo Sun, 29 Nov at 03:00 pm Blue Bamboo Center For The Arts ENTERTAINMENT
The Jazz Room: A Journey to the Heart of New Orleans Sun, 13 Dec at 04:00 pm Orlando Museum of Art USD 46 TO 68 MUSIC
Swing Swing with Steve Roman and his orchestra a tribute to Sammy Davis Jr Fri, 16 Oct at 07:00 pm Aloma Cinema & Grill USD 27 MUSIC
Orlando Jazz Orchestra Holiday Show | December 6 | Blue Bamboo Sun, 06 Dec at 03:00 pm Blue Bamboo Center For The Arts MUSIC
Candlelight: Tribute to Adele Sat, 28 Nov at 06:00 pm Orlando Museum of Art USD 36 TO 87 CANDLELIGHT-CONCERTS
Patrick Lamb | December 18 | Blue Bamboo Fri, 18 Dec at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 ENTERTAINMENT
Candlelight: 90s Hip-Hop on Strings Sat, 28 Nov at 08:30 pm Orlando Museum of Art USD 36 TO 59 CANDLELIGHT-CONCERTS
Candlelight: Christmas Carols on Strings Fri, 18 Dec at 08:30 pm Orlando Museum of Art USD 38 TO 80 ENTERTAINMENT
The Lowdown - Tenor/Bass Choral Festival 2026 Fri, 30 Oct at 10:00 am John M. Tiedtke Concert Hall USD 27 FITNESS