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

1st Annual Holler Ford Racing Showcase

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

24th Annual MLK Celebration Unity Heritage Festival

 Sun, 18 Jan at 11:00 am Winter Park Community Center Free

Candlelight: Valentine's Day Special - Winter Park

 Thu, 12 Feb at 06:30 pm 1300 S Denning Dr, Winter Park, FL

Candlelight: Best of Hip-Hop

 Thu, 22 Jan at 07:00 pm Mead Botanical Garden

2026 Winter Park Fashion Week Show

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

Love Your Library: Books & Boots

 Sat, 07 Feb at 07:00 pm 1052 W Morse Blvd, Winter Park, FL, United States, Florida 32789

Girl The PARK Day! FREE EVENT | Daytime Vibes!

Sun, 25 Jan at 02:00 pm Blue Jacket Park

Concertos by Candlelight: Guilmant, Paganini, Rachmaninoff

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

Age of Enlightenment: Haydn, Mozart, Beethoven

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

Concertos by Candlelight: Guilmant, Paganini, Rachmaninoff

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

YOGA BLISS - A Musical Journey to Inner Peace- Free Concert

 Sat, 31 Jan at 07:00 pm Bush Auditorium Free

Ella & the Bossa Beat

 Sat, 31 Jan at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

Dinosaur Pile Up at Conduit

 Tue, 03 Feb at 07:00 pm Conduit

GROOVE SLAYERS - Saturday Dance Fever! LIVE at Aloma Cinema Grill

 Sun, 18 Jan at 06:00 pm Aloma Cinema Grill USD 25 to 36

Jeff Rupert Quartet

 Fri, 23 Jan at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

Bobby Jo Valentine Concert

 Fri, 23 Jan at 07:00 pm St Richard's Episcopal Church USD 13

St. John Passion | J.S. Bach

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

BachataYá

Fri, 23 Jan at 07:00 pm The Trap

Free for Seniors: Solo Mio

 Tue, 10 Feb at 02:00 pm Aloma Cinema Grill Free

Silver Screen Classics

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

Derby on Park (Kentucky Derby Party)

 Sat, 02 May at 04:30 pm Winter Park Events Center

Silver Screen Classics

 Sun, 26 Apr at 03:00 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

Golden Flower with the Mudita Orchestra

 Fri, 13 Feb at 08:00 pm Blue Bamboo Center For The Arts

FREE Valentine's Concert in the Park- Swing into Romance

 Fri, 13 Feb at 07:30 pm Central Park In Winter Park, Florida

Sculpting Sound

 Thu, 29 Jan at 06:00 pm Albin Polasek Museum & Sculpture Gardens Free

Cigano Swing

Fri, 30 Jan at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

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

I LOVE R&B PARTY - Orlando, FL

 Fri, 06 Feb at 09:00 pm CONDUIT

The Chosen Phoo, Fiddler's Green!

 Sat, 24 Jan at 09:00 pm Fiddlers Green Irish Pub & Eatery

Free Matinee for Seniors: Sarah’s Oil

 Thu, 05 Feb at 12:00 pm Aloma Cinema Grill Free

Free for Seniors: Solo Mio

 Mon, 09 Feb at 12:00 pm Aloma Cinema Grill Free

Free Movie for Seniors: Green & Gold

 Tue, 20 Jan at 02:00 pm Aloma Cinema Grill Free

Steve Luciano Quartet featuring Dan Jordan

 Sun, 18 Jan at 03:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

The Dark Eighties Dance Party - Florida Debut at Conduit!

 Fri, 13 Feb at 09:00 pm 6700 Aloma Ave, Winter Park, FL 32792, United States

Live at the Blue Bamboo

 Fri, 30 Jan at 08:00 pm Blue Bamboo Center For The Arts

80s Dance Party Orlando!

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

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

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

Fire From The Gods at Conduit

 Thu, 29 Jan at 06:00 pm Conduit

Ivories In Harmony with Carol Stein and Michael Mastroianni

 Sun, 25 Jan at 03:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

All the Line Non-Profit Launch Event!

 Wed, 04 Feb at 06:30 pm Aloma Cinema Grill

Jason V. @ Tommy Bahama Marlin Bar, Winter Park

Sun, 25 Jan at 04:00 pm Tommy Bahama (Winter Park, FL)

Free Movie: Signing Tony Raymond

 Thu, 29 Jan at 07:00 pm Aloma Cinema Grill Free

Orlando Women Social Club Meetup to Discuss Films and Connect

 Thu, 29 Jan at 07:50 pm Regal Winter Park Village Free

K*ll Lincoln

 Sat, 20 Jun at 07:00 pm Conduit

Glare

 Fri, 23 Jan at 07:00 pm Conduit

Finally Famous: Live - An Industry Professional IRL Experience

 Sun, 25 Jan at 06:00 pm 7200 Aloma Ave USD 16 to 31

MamboYá Social

 Sun, 18 Jan at 05:00 pm The Trap

Roots & Flow: A Brazilian Zouk Weekend with Iago & Ninna

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

MamboYá Social

 Sun, 25 Jan at 05:00 pm The Trap

Florida Wildlife Corridor Film Screenings At Rollins College

 Tue, 27 Jan at 07:00 pm Bush Science Center Free

Arts Weekend Community Concert Featuring Broadway Star Jasmine Forsberg

 Fri, 06 Feb at 07:00 pm 251 S Park Ave, Winter Park, FL 32789, United States

Pablo Aragona Quintet

 Sat, 24 Jan at 08:00 pm Blue Bamboo Center For The Arts

The Sax Therapyst Experience

 Wed, 21 Jan at 07:00 pm Morse Code Lounge USD 18 to 87

Pedals, Pipes, and Pizza for young musicians

Sat, 24 Jan at 10:00 am All Saints Church of Winter Park

Glare with All Under Heaven

 Sat, 24 Jan at 11:30 pm Conduit

Free Movie for Seniors: Signing Tony Raymond

 Wed, 28 Jan at 04:00 pm Aloma Cinema Grill Free

Broadway Love Songs Concert

 Sat, 14 Feb at 04:00 pm All Saints Episcopal Church USD 30

Rod Stewart Tribute "Forever Mod" LIVE at Aloma Cinema Grill

 Thu, 05 Feb at 07:00 pm Aloma Cinema Grill USD 25 to 36

Free Movie for Seniors: Green & Gold

 Mon, 19 Jan at 12:00 pm Aloma Cinema Grill Free

Free Movie for Seniors: Signing Tony Raymond

 Mon, 26 Jan at 12:00 pm Aloma Cinema Grill Free

Galentine's Day Paint Party @ All Fired Up

 Thu, 12 Feb at 06:00 pm All Fired Up

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

Dueling Piano Brunch at Tibby's Winter Park!

 Sun, 25 Jan at 11:00 am Tibby's New Orleans Kitchen (Winter Park, FL)

ORL Film Bar Monday - 4th Monday in Winter Park

 Mon, 26 Jan at 06:00 pm Fiddlers Green Irish Pub & Eatery

Organ Recital Colin MacKnight

 Fri, 06 Feb at 07:30 pm Knowles Memorial Chapel

Free Movie for Seniors: Signing Tony Raymond

 Tue, 27 Jan at 02:00 pm Aloma Cinema Grill Free

January 2026 - Evening Meeting - Full Sail University

 Mon, 26 Jan at 06:00 pm Full Sail University USD 29

69th Season Jazz Finale

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

A Killer's Confession

 Sat, 28 Feb at 07:00 pm Conduit

Zombie Apocalypse: Thriller's Anniversary Show

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

Nordic Choir Winter Tour: Winter Park, FL

 Tue, 03 Feb at 07:00 pm St. John Lutheran Church

Lysander Piano Trio

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

Fête Minuet 18th Century Ball

 Sun, 18 Jan at 06:00 pm 200 W New England Ave, Winter Park, FL 32789-4226, United States

Clarinet Candy! The Licorice Sticks Clarinet Orchestra

Sun, 08 Feb at 03:00 pm Blue Bamboo Center For The Arts

Dinosaur Pile-Up

 Wed, 04 Feb at 12:00 am Conduit

An Evening of Story Songs

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

Jeris Johnson

 Thu, 19 Feb Conduit

Winter Park M**der Mystery: Catch the Killer!

 Sat, 31 May at 11:00 am Peacock Fountain USD 10 to 20

Wheel - Band

 Wed, 11 Feb Conduit

Felandi’s fame in heaven

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

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

Timecop1983

 Thu, 05 Mar at 12:00 am Conduit

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

Pump Action

 Fri, 24 Apr Conduit

Rollins College Summer Music Vocal Academy 2026

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

Winter Park's Secret Society: Mystery Hunt

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

Parrot Heads of Central Florida SECOND THURSDAY PHlocking!

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