Entertainment events in Winter Park

Check out happening entertainment events all around Winter Park, FL

Free Movie for Seniors: Downton Abbey: Grand Finale

 Tue, 16 Sep at 12:00 pm Aloma Cinema Grill Free

Free Movie for Seniors: Downton Abbey: Grand Finale

 Thu, 18 Sep at 12:00 pm Aloma Cinema Grill Free

John Maus in Winter Park

 Sat, 11 Oct at 07:00 pm Conduit

Candlelight: Best of Hip-Hop

 Thu, 25 Sep at 07:00 pm Mead Botanical Garden

Pinkshift in Winter Park

 Wed, 15 Oct at 06:30 pm Conduit

Ulcerate, Spirit Possession in Winter Park

 Thu, 06 Nov at 07:00 pm Conduit

Averly Morillo in Winter Park

 Sat, 11 Oct at 06:00 pm Calvary Orlando

Women’s Social Club Dip Into Fall Signature Experience (Winter Park)

 Sat, 13 Sep at 11:00 am Peterbrooke Chocolatier of Winter Park USD 69

Skizzy Mars in Winter Park

 Sat, 08 Nov at 07:00 pm Conduit

Free Movie for Seniors: The Senior

 Wed, 01 Oct at 12:00 pm Aloma Cinema Grill Free

Hot In Herre: 2000s Dance Party

 Fri, 19 Sep at 07:00 pm Conduit

Jon Breaks Bad News at Conduit

 Fri, 19 Sep at 07:00 pm Conduit

Gilson & Jessica LambaZouk Weekender

 Fri, 19 Sep at 08:00 pm Winter Park Ballroom Dance Co.

Living Dead Girl CONSPIRACY Album Release Party

 Fri, 10 Oct at 07:00 pm 6700 Aloma Ave, Winter Park, FL 32792-6801, United States

Free Movie for Seniors: The Bucket List Matinee

 Tue, 30 Sep at 01:00 pm Aloma Cinema Grill Free

Ultimate RUSH Tribute at Aloma Cinema Grill

 Sat, 20 Sep at 07:00 pm Aloma Cinema Grill USD 27

A Lot Like Birds

 Fri, 03 Oct at 07:00 pm Conduit

Peace Day in the Park

 Sat, 20 Sep at 09:00 am Central Park Main Stage Free

Rachel Ombredane & Rosaway – Live at Blue Bamboo

 Sat, 04 Oct at 08:00 pm Blue Bamboo Center For The Arts

Hollywood Hits: Live Orchestra Concert

 Tue, 30 Sep at 02:00 pm Blue Bamboo Center for the Arts Free

John Maus

 Fri, 10 Oct at 07:00 pm Conduit

Winter Park Village Fall Concert Series

 Tue, 23 Sep at 06:00 pm Winter Park Village

Bras Beaters Bags Belts and Brims

 Sat, 04 Oct at 04:00 pm Winter Park Community Center USD 29

Tribute to Black Sabbath by WarPigz

 Sat, 13 Sep at 07:00 pm Aloma Cinema Grill USD 29 to 55

Pinkatude

 Sat, 18 Oct at 05:00 pm Winter Park Community Center USD 50 to 642

Sunday Brunch with Saxophonist Vicente Belen at Tibbys in Winter Park

 Sun, 21 Sep at 11:00 am Tibby's New Orleans Kitchen Free

Free Movie for Seniors: The Senior

 Mon, 29 Sep at 12:00 pm Aloma Cinema Grill Free

Emo Night Karaoke at Conduit

 Fri, 07 Nov at 08:00 pm Conduit

Greg Diaz & The Art Of Imagination Quintet

 Fri, 12 Sep at 08:00 pm Blue Bamboo Center For The Arts

Live Music at VINIA Wine & Kitchen

 Thu, 18 Sep at 07:00 pm VINIA Wine & Kitchen

Orlando's Westie Mashup with Pro Gary Jobst & DJ Gunner

 Sat, 20 Sep at 07:00 pm Winter Park Ballroom Dance Co.

Candlelight: Neo-Soul and Hip-Hop Favorites | Orlando

 Fri, 19 Sep at 06:30 pm Azalea Lodge at Mead Botanical Garden

52nd Annual Autumn Art Festival

 Sat, 11 Oct at 09:00 am Central Park In Winter Park, Florida

Tuesday Trivia at The Porch Winter Park

 Tue, 09 Sep at 07:30 pm The Porch Winter Park

The Last Dive screens at Global Peace Film Festival

 Fri, 19 Sep at 07:30 pm Winter Park Library

The Legendary Pink Dots at Conduit

 Thu, 16 Oct at 07:00 pm Conduit

Free for Seniors: Swing Into September Dance

 Wed, 10 Sep at 03:00 pm Winter Park Community Center Free

Crypta at Conduit

 Sun, 14 Sep at 07:00 pm Conduit

The Sage Project Phase III: Hannibal Square Elders Tell Their Stories

 Fri, 19 Sep at 07:00 pm Hannibal Square Heritage Center

Peter Schreyer: Small Stories From a Big Country

 Fri, 26 Sep at 07:00 pm Crealdé School of Art

Tuesday Trivia at The Porch Winter Park

 Tue, 16 Sep at 07:30 pm The Porch Winter Park

Six Feet Under

 Wed, 24 Sep at 07:00 pm Conduit

The Presidents' Tailor @ Winter Park Library, FL

 Tue, 09 Sep at 06:30 pm 1052 W Morse Blvd, Winter Park, FL 32789-3760, United States

John Maus at Conduit

 Sat, 11 Oct at 08:00 pm Conduit

Mean Mary in Winter Park, FL

 Sat, 25 Oct at 08:00 pm Blue Bamboo Center For The Arts

Tuesday Trivia at The Porch Winter Park

 Tue, 23 Sep at 07:30 pm The Porch Winter Park

Rachel Ombredane and RoSaWay in Concert

 Sat, 04 Oct at 08:00 pm Blue Bamboo Center For The Arts

I Set My Friends On Fire

 Fri, 26 Sep at 07:00 pm Conduit

The Cosmic Jam Concert & The Grateful Dead Movie

 Fri, 03 Oct at 07:00 pm Aloma Cinema Grill USD 29

2nd Annual Legacy Gala

 Fri, 03 Oct at 06:00 pm Winter Park Events Center

A Tarot "Reading" by Noah Lugeons

 Sun, 21 Sep at 02:00 pm University Club of Winter Park

Johnny Mercer Tribute with Michael Kramer/Greg Parnell Trio

 Sun, 14 Sep at 03:00 pm Blue Bamboo Center For The Arts

Daft Disko Halloween

 Thu, 30 Oct Conduit

Pinkshift at Conduit

 Wed, 15 Oct at 06:30 pm Conduit

Concertos by Candlelight: Guilmant, Paganini, Rachmaninoff

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

Live Music at VINIA Wine & Kitchen

 Thu, 23 Oct at 07:00 pm VINIA Wine & Kitchen

The Boneshakers featuring Randy Jacobs and Jenny Langer

 Fri, 17 Oct at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

Silent Theory

 Tue, 30 Sep at 07:00 pm Conduit

Candlelight: Queen vs. ABBA

 Wed, 22 Oct at 07:00 pm Mead Botanical Garden

Signs of The Swarm

 Sat, 25 Oct at 07:00 pm Conduit

SSL Road Show: Meet The New Oracle Console At Full Sail

 Wed, 24 Sep at 05:00 pm Full Sail Free

Candlelight: Tribute to Bad Bunny | Orlando

 Thu, 25 Sep at 06:30 pm Azalea Lodge at Mead Botanical Garden

Arlie at Conduit

 Wed, 22 Oct at 07:00 pm Conduit

Live Music at VINIA Wine & Kitchen

 Thu, 11 Sep at 07:00 pm VINIA Wine & Kitchen

Signs Of The Swarm (18+)

 Sun, 26 Oct at 09:30 pm Conduit

Orlando Club Sport Player's Party

 Sat, 27 Sep at 04:00 pm Trick Shots Winter Park

Willy & The Pour Boys-LIVE @ Fiddler’s

Sun, 28 Sep at 05:00 pm Fiddlers Green Irish Pub & Eatery

For the Living screening at Global Peace Film Festival

 Thu, 18 Sep at 07:30 pm Winter Park Library

Orlando's Westie Mashup with Lecie Langille & DJ Kyle Hebert

 Sat, 15 Nov at 07:00 pm Winter Park Ballroom Dance Co.

Oceano at Conduit

 Sun, 05 Oct at 05:00 pm Conduit

Live Music at VINIA Wine & Kitchen

 Thu, 25 Sep at 07:00 pm VINIA Wine & Kitchen

Andre Lash in Concert

 Tue, 16 Sep at 07:30 pm Rollins College

Live Music at VINIA Wine & Kitchen

 Thu, 09 Oct at 07:00 pm VINIA Wine & Kitchen

South Arcade

 Mon, 06 Oct at 07:00 pm Conduit

2026 Winter Park Fashion Week Show

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

Abraham’s Bridge & Fiddler on the Moon: Judaism in Space GPFF 2025

 Thu, 18 Sep at 05:30 pm Winter Park Library

Orlando's Westie Mashup with Pro Christopher Rupp & DJ Lilgem

 Sat, 20 Dec at 07:00 pm Winter Park Ballroom Dance Co.

HAPCO Music Foundation presents big band energy from Josephine Swing

 Fri, 21 Nov at 08:00 pm Blue Bamboo Center For The Arts

Revocation

 Wed, 12 Nov at 07:00 pm Conduit

She Runs The World Global Peace Film Festival Screening

 Wed, 17 Sep at 06:30 pm Bush Auditorium

Arlie - Band

 Tue, 21 Oct at 07:00 pm Conduit

Ulcerate

 Wed, 05 Nov at 07:00 pm Conduit

Maitland Jazz Stage Band: Honoring the Legacy of Big Band Music

 Sun, 21 Sep at 03:00 pm Blue Bamboo Center For The Arts

A Christmas Romance Tour with Marcus Anderson & Rebecca Jade

 Fri, 19 Dec at 08:00 pm 460 E. New England Ave., Winter Park, FL, United States, Florida 32789

The Best Christmas Pageant Ever

 Fri, 12 Dec at 07:00 pm Shaeffer Hall at St. John Church

Live Music at VINIA Wine & Kitchen

 Thu, 30 Oct at 07:00 pm VINIA Wine & Kitchen

Concertos by Candlelight: Guilmant, Paganini, Rachmaninoff

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

CFWA October Networking Event at Villa Tuscany at WinterClub

 Tue, 07 Oct at 06:30 pm Villa Tuscany USD 50 to 61

Narcotic Wasteland

 Tue, 16 Sep at 07:00 pm Conduit

South Arcade at Conduit

 Tue, 07 Oct at 07:30 pm Conduit

Greyhaven

 Fri, 21 Nov at 07:00 pm Conduit

Brothers After All - Allman Brothers Tribute Debut at Aloma Cinema Theater

 Thu, 30 Oct at 07:00 pm Aloma Cinema Grill USD 29 to 55

Daniel Adam Maltz, fortepiano with Bach Chamber Choir and Orchestra

 Sun, 19 Oct at 03:00 pm Tiedtke Concert Hall | 1000 Holt Ave, Winter Park, FL 32789-4499, United States

Emo Night Karaoke

 Thu, 06 Nov at 07:00 pm Conduit

Winter Park Community Jam - September 18, 2025

 Thu, 18 Sep at 06:30 pm Winter Park Community Center 721 New

Yule Be Sorry You Asked

 Sat, 13 Dec at 03:00 pm Shaeffer Hall at St. John Church

Pinkshift

 Tue, 14 Oct at 07:00 pm Conduit

Entheos

 Tue, 02 Dec at 07:00 pm Conduit

A Classic Christmas

 Sat, 13 Dec at 01:00 pm Knowles Memorial Chapel

Age of Enlightenment: Haydn, Mozart, Beethoven

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