Entertainment events in Winter Park

Check out happening entertainment events all around Winter Park, FL

AdventHealth Winter Park Road Race 10k and 2 Mile

 Sat, 28 Mar at 07:00 am Park Avenue Central Park

Taste of Winter Park

 Wed, 01 Apr at 06:30 pm Winter Park Farmers' Market Venue USD 55 to 384

1st Annual Holler Ford Racing Showcase

 Sat, 14 Mar at 05:00 pm 1875 South Orlando Avenue, Maitland, FL, United States, Florida 32751

2026 Winter Park Fashion Week Show

 Sat, 21 Feb at 06:00 pm Full Sail Live USD 150 to 1,069

Age of Enlightenment: Haydn, Mozart, Beethoven

 Sun, 22 Feb at 03:00 pm Knowles Memorial Chapel

Nick Dumas & Branchline | Feb 20 | Blue Bamboo

 Fri, 20 Feb at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

Jeff Rupert Quartet | Feb 28 | Blue Bamboo

 Sat, 28 Feb at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

Orlando Gay Chorus Presents: "Love Is...A Drag" Cabaret

 Sat, 21 Feb at 08:00 pm Blue Bamboo Center For The Arts

Allyson Briggs | Feb 22 | Blue Bamboo

 Sun, 22 Feb at 03:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

Concertos by Candlelight: Guilmant, Paganini, Rachmaninoff

 Fri, 20 Feb at 07:30 pm Knowles Memorial Chapel

Cassadee Pope

 Sat, 07 Mar Conduit

Concertos by Candlelight: Guilmant, Paganini, Rachmaninoff

 Sat, 21 Feb at 07:30 pm Knowles Memorial Chapel

BacahataYá Social

 Fri, 27 Feb at 07:00 pm The Trap

Fat Tuesday Mardi Gras Block Party at Tibby's in Winter Park

 Tue, 17 Feb at 05:00 pm Tibby's New Orleans Kitchen Free

St. John Passion | J.S. Bach

 Sun, 01 Mar at 03:00 pm Knowles Memorial Chapel

MamboYá Social - Rumba Edition

 Sun, 22 Feb at 05:00 pm The Trap

Silver Screen Classics

 Sat, 25 Apr at 07:30 pm Knowles Memorial Chapel

Silver Screen Classics

 Sun, 26 Apr at 03:00 pm Knowles Memorial Chapel

Sacred Service Duke Ellington with Samuel McKelton

 Fri, 10 Apr at 07:30 pm Knowles Memorial Chapel

Ultimate Santana Tribute LIVE at Aloma Cinema Grill in Winter Park, FL

 Sat, 28 Feb at 07:00 pm Aloma Cinema Grill USD 22 to 30

80s Dance Party Orlando!

 Fri, 20 Mar at 08:00 pm 6700 Aloma Ave, Winter Park, FL 32792, United States

BLUES BROTHERS MOVIE Tribute ANOTHER MISSION FROM GOD at Aloma Cinema Grill

 Sat, 28 Mar at 07:00 pm Aloma Cinema Grill USD 25 to 36

Palm Beach Society Orchestra plays The Blue Bamboo

 Sun, 01 Mar at 03:00 pm Blue Bamboo Center For The Arts

DIAMOND: A Neil Diamond Tribute LIVE at Aloma Cinema Grill in Winter Park!

 Sat, 18 Apr at 07:00 pm Aloma Cinema Grill USD 29 to 39

A White Rose Jazz & Gospel Affair

 Sun, 19 Apr at 12:00 pm The Alfond Inn USD 0 to 10,673

Dueling Piano Brunch at Tibby's Winter Park!

 Sun, 22 Feb at 11:00 am Tibby's New Orleans Kitchen (Winter Park, FL)

Nick Dumas & Branchline @ Blue Bamboo Center for the Arts!

 Fri, 20 Feb at 08:00 pm Blue Bamboo Center For The Arts

Legendary: Celebrating 40 Years of Zelda

 Sat, 21 Feb at 07:00 pm Conduit

Edgewater High School PTSO Presents: Sip & Soar | Mardi Gras

 Fri, 27 Feb at 07:00 pm Celebration Gardens USD 65 to 500

Roots & Flow: A Brazilian Zouk Weekend with Felipe & Bruna

 Fri, 20 Feb at 08:00 pm Winter Park Ballroom Dance Co.

Jeris Johnson

 Fri, 20 Feb at 11:00 pm Conduit

Brookshire Carnival

 Sat, 28 Feb at 02:00 pm 2500 Cady Way, Winter Park, FL

69th Season Jazz Finale

 Sat, 09 May at 03:00 pm Blue Bamboo Center For The Arts

Free Movie for Seniors: I Can Only Imagine 2

 Tue, 24 Feb at 12:00 pm Aloma Cinema Grill Free

Ladies’ Sip and Dip Party in the Park (Orlando)

 Sat, 07 Mar at 03:30 pm Blue Jacket Park

Old Time Sailors and More

 Thu, 16 Apr at 07:00 pm Conduit USD 20

Live Music at VINIA Wine & Kitchen

 Thu, 19 Feb at 07:00 pm VINIA Wine & Kitchen

The M Factor 2: Before the Pause- Perimenopause

 Tue, 17 Feb at 07:30 pm Trinity Preparatory School USD 13

Groove Slayers - Earth, Wind and Fire Tribute at Aloma Cinema Grill

 Fri, 27 Mar at 07:00 pm Aloma Cinema Grill

Free Matinee for Seniors: Sweetwater

 Tue, 17 Feb at 12:00 pm Aloma Cinema Grill Free

Danny Worsnop & Tyler Rich in Orlando

 Thu, 09 Apr at 06:30 pm Conduit USD 98 to 214

Brian Smalley live at the Blue Bamboo in Winter Park

 Fri, 06 Mar at 08:00 pm Blue Bamboo Center For The Arts

A Killer's Confession

 Sat, 28 Feb at 07:00 pm Conduit

Karaoke Night - Winter Park!

 Fri, 20 Feb at 06:45 pm Aloma Bowling Center

Passion Music for Early America with Bach Vocal Artists

 Thu, 26 Mar at 07:30 pm Tiedtke Concert Hall | 1000 Holt Ave, Winter Park, FL 32789-4499, United States

Copy of Musical BINGO Mondays at Aloma Cinema Grill in Winter Park, FL!

 Mon, 16 Feb at 06:30 pm Aloma Cinema Grill Free

Musical BINGO Mondays at Aloma Cinema Grill in Winter Park, FL!

 Mon, 23 Feb at 06:30 pm Aloma Cinema Grill Free

Full Circle After Hours Networking w The 360 Exchange!

Wed, 25 Feb at 06:30 pm Winter Park Pines Golf Club

Essenger at Conduit

 Wed, 06 May at 07:00 pm Conduit

Copy of Musical BINGO Mondays at Aloma Cinema Grill in Winter Park, FL!

 Mon, 09 Mar at 06:30 pm Aloma Cinema Grill Free

Lysander Piano Trio

 Sun, 15 Mar at 03:00 pm Tiedtke Concert Hall | 1000 Holt Ave, Winter Park, FL 32789-4499, United States

Musical BINGO Mondays at Aloma Cinema Grill in Winter Park, FL!

 Mon, 16 Mar at 06:30 pm Aloma Cinema Grill Free

Musical BINGO Mondays at Aloma Cinema Grill in Winter Park, FL!

 Mon, 23 Mar at 06:30 pm Aloma Cinema Grill Free

Jeris Johnson

 Thu, 19 Feb at 07:00 pm Conduit

Siamese Tickets

Sat, 28 Feb at 07:00 pm Winter Park Florida

K*ll Lincoln

 Sat, 20 Jun at 07:00 pm Conduit

Gala of Ghouls

 Thu, 26 Feb at 07:00 pm Conduit

An Evening of Story Songs

Fri, 27 Feb at 11:00 pm Blue Bamboo Center For The Arts

Musical BINGO Mondays at Aloma Cinema Grill in Winter Park, FL!

 Mon, 02 Mar at 06:30 pm Aloma Cinema Grill Free

Live Music at VINIA Wine & Kitchen

 Thu, 26 Feb at 07:00 pm VINIA Wine & Kitchen

Mac Sabbath in Orlando

 Sat, 11 Apr at 06:00 pm Conduit USD 34

Musical BINGO Mondays at Aloma Cinema Grill in Winter Park, FL!

 Mon, 06 Apr at 06:30 pm Aloma Cinema Grill Free

Melissa Gamal in Orlando – One-Day Belly Dance Intensive

 Sat, 16 May at 10:00 am 6904 Aloma Ave, Winter Park, FL, United States, Florida 32792

Musical BINGO Mondays at Aloma Cinema Grill in Winter Park, FL!

 Mon, 30 Mar at 06:30 pm Aloma Cinema Grill Free

Timecop1983

 Thu, 05 Mar at 12:00 am Conduit

Felandi’s fame in heaven

 Sat, 25 Apr at 08:45 am Conduit USD 13

The Glorious Redemption Concert

 Sat, 04 Apr at 04:00 pm The Agape Hall USD 13 to 31

Essenger - Artist

 Tue, 05 May Conduit

3rd Annual Lets Take a Mental Health Break(fast)

 Wed, 29 Apr at 08:30 am 2005 Mizell Ave suite 1700 USD 0 to 26,679

Weedeater, Conan, and More in Orlando

 Thu, 02 Apr at 07:00 pm Conduit USD 34

By Storm

 Mon, 11 May Conduit

By Storm at Conduit

 Tue, 12 May at 07:00 pm Conduit

Winter Park's Secret Society: Mystery Hunt

 Sat, 19 Jul at 10:00 am 445 N Park Ave USD 10 to 20

Pump Action

 Fri, 24 Apr at 07:00 pm Conduit

Free Movie for Seniors: I Can Only Imagine 2

 Wed, 25 Feb at 02:00 pm Aloma Cinema Grill Free

Rollins College Summer Music Vocal Academy 2026

 Sun, 21 Jun at 04:00 pm Rollins College USD 60 to 275

Laughter For Social Change - Comedy Show ACEs Awareness 05-27-2026

 Wed, 27 May at 06:30 pm Winter Park Village USD 29 to 444

Poison The Well (18+)

 Tue, 24 Mar at 11:00 pm Conduit

Zombie Apocalypse: Thriller's Anniversary Show

 Fri, 27 Mar at 08:00 pm 1335 Howell Branch Rd USD 30 to 400

ORL Film Bar Monday - 4th Monday in Winter Park

 Mon, 23 Feb at 06:00 pm Fiddlers Green Irish Pub & Eatery

Parrot Heads of Central Florida SECOND THURSDAY PHlocking!

 Thu, 14 Aug at 05:00 pm The Porch Winter Park Free

Unwritten Law

 Mon, 16 Feb at 12:00 am Conduit