Upcoming Live Music Events

Candlelight: 90s Hip-Hop on Strings

 Azalea Lodge at Mead Garden 5 Jun 2026
ENTERTAINMENT USD 51 TO 102

Candlelight: Mozart vs. Beethoven

 Orlando Museum of Art 25 Jul 2026
CANDLELIGHT-CONCERTS USD 36 TO 82

Candlelight: Tribute to Bad Bunny

 Azalea Lodge at Mead Garden 22 May 2026
ENTERTAINMENT USD 51 TO 101

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Upcoming Comedy Events

The Disappearing Duck: A Mystery Dinner Experience (Winter Park)

 Agave Azul Cocina Mexicana (Winter Park) 17 May 2026

The Disappearing Duck: A Mystery Dinner Experience (Winter Park)

 Agave Azul Winter Park 17 May 2026
MEETUPS USD 20

Once Upon a Mattress: Youth Edition

 Trinity Preparatory School Auditorium 29 May 2026
ART

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Upcoming Food & Drinks Events

Rollins Men’s Soccer Elite Overnight Camps 2026

 Cahall-Sandspur Field 4 Jun 2026
WORKSHOPS USD 470 TO 676

Brunch on Bourbon with Live Music by Seth Pause at Tibby's in Winter Park

 Tibby's New Orleans Kitchen 24 May 2026
MUSIC FREE

8/29 BLUES BROTHERS Tribute "ANOTHER MISSION FROM GOD" Aloma Cinema Grill

 Aloma Cinema Grill 29 Aug 2026
ENTERTAINMENT USD 25 TO 36

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Upcoming Festivals Events

Winter Park Arts Festival

 Central Park 10 Jul 2026
ART FREE

Die Sexual in Orlando

 Conduit 11 Jun 2026
FESTIVALS USD 28

The Community Market

 Agape Hall 17 May 2026
MEETUPS FREE

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Upcoming Pop-Ups Events

Orlando International Fashion Week Presents - 626 Euphoria

 Winter Park Events Center 6 Jun 2026
FASHION

Orlando International Fashion Week Presents - 626 Euphoria

 Winter Park Events Center 6 Jun 2026
FASHION USD 55 TO 82

Pop Up Flow at AJ Chocolate House

 AJ Chocolate House 6 Jun 2026
POP-UPS FREE

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Trending Events in Winter Park

Winter Park Murder Mystery 2: Crime on Date Night!

 Winter Park Historical Association 1 Jun 2026
TRIPS-ADVENTURES USD 15

Sword II in Orlando

 Conduit 7 Jun 2026
MUSIC USD 28

Read, White, and Blue Celebration!

 Winter Park Library, West Morse Boulevard, Winter Park, FL, USA 30 May 2026
FESTIVALS

American Maestro: The Music of John Williams

 Calvary Orlando 22 May 2026
ENTERTAINMENT

Candlelight: Coldplay & Imagine Dragons

 Azalea Lodge at Mead Garden 25 Jun 2026
ENTERTAINMENT USD 51 TO 84

Candlelight: Tribute to Juan Gabriel on Strings

 Azalea Lodge at Mead Garden 4 Jun 2026
ENTERTAINMENT USD 68

AdventHealth July 4th Watermelon 5K

 251 S Park Ave, Winter Park, FL 32789, United States 4 Jul 2026
FOURTH-OF-JULY

Six Feet Under and Kataklysm (18+)

 Conduit 19 Jul 2026
CONTESTS

Smooth Sessions at Blue Bamboo with Althea Rene´

 Blue Bamboo Center for the Arts 6 Jun 2026
MUSIC USD 39 TO 55

Six Feet Under, Kataklysm, Wormhole in Winter Park

 Conduit 19 Jul 2026
CONCERTS

Rollins Summer Volleyball Camps 2026

 Alfond Sports Center 11 May 2026
SPORTS USD 164 TO 497

Rollins Summer Co-Ed Indoor Camp 2026

 Alfond Sports Center 26 May 2026
SUMMER-CAMPS USD 211 TO 367

Alejandro Aranda at Conduit

 Conduit 16 Jun 2026
TRIPS-ADVENTURES

Orlando Park Avenue Art Expo

 Central Park 17 Jul 2026
ART FREE

Rollins Summer Half-Day Junior Elite Camp 2026

 Cahall-Sandspur Field 8 Jun 2026
SUMMER-CAMPS USD 290

More things to do in Winter Park

Live Music
Comedy
Food & Drinks
Festivals
Pop-Ups
Carnivals
Music Festivals
St. Patrick's Day
Speed Dating