Upcoming Festivals Events

Smile Mile - Kids Run

 Blue Jacket Park 14 Mar 2026
KIDS

24th Annual MLK Celebration Unity Heritage Festival

 Winter Park Community Center 18 Jan 2026
FESTIVALS FREE

Concertos by Candlelight: Guilmant, Paganini, Rachmaninoff

 Knowles Memorial Chapel 21 Feb 2026
CONCERTS

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Upcoming Live Music Events

VOCES8 in Winter Park

 Knowles Memorial Chapel 15 Feb 2026
ART

Love Your Library: Books & Boots

 1052 W Morse Blvd, Winter Park, FL, United States, Florida 32789 7 Feb 2026
MUSIC

Age of Enlightenment: Haydn, Mozart, Beethoven

 Knowles Memorial Chapel 22 Feb 2026
ENTERTAINMENT

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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

Sourdough Pizza (Winter Park)

 The Ancient Olive Gourmet of Winter Park 25 Jan 2026
WORKSHOPS USD 82

Derby on Park (Kentucky Derby Party)

 Winter Park Events Center 2 May 2026
KENTUCKY-DERBY

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Upcoming Pop-Ups Events

OIFW Summer Shows: Winter Park Events Center (Multiple Shows 3pm & 7pm)

 Winter Park Events Center 6 Jun 2026
FASHION USD 55 TO 71

Orlando Local Makers at Foxtail Coffee Winter Park!

 Foxtail Coffee (Winter Park, FL) 1 Feb 2026
POP-UPS

Community Treasures Pop Up

 Redeemer Lutheran Church 18 Jan 2026
FREE

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Upcoming Comedy Events

Free for Seniors: Solo Mio

 Aloma Cinema Grill 9 Feb 2026
ENTERTAINMENT FREE

Free Movie: Signing Tony Raymond

 Aloma Cinema Grill 29 Jan 2026
ENTERTAINMENT FREE

Free Movie for Seniors: Signing Tony Raymond

 Aloma Cinema Grill 27 Jan 2026
ENTERTAINMENT FREE

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Upcoming Music Festivals Events

Silver Screen Classics

 Knowles Memorial Chapel 25 Apr 2026
ENTERTAINMENT

Silver Screen Classics

 Knowles Memorial Chapel 26 Apr 2026
ENTERTAINMENT

Lysander Piano Trio

 Tiedtke Concert Hall | 1000 Holt Ave, Winter Park, FL 32789-4499, United States 15 Mar 2026
MUSIC

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Trending Events in Winter Park

AdventHealth Winter Park Road Race 10k and 2 Mile

 Park Avenue Central Park 28 Mar 2026
SPORTS

Park Ave 5k Presented by AdventHealth

 Stage at Central Park 17 Jan 2026
KIDS

AdventHealth Run 4 Love 4 Mile

 250 Perth Ln, Winter Park, FL 32792, United States 14 Feb 2026
SPORTS

1st Annual Holler Ford Racing Showcase

 1875 South Orlando Avenue, Maitland, FL, United States, Florida 32751 14 Mar 2026
SPORTS

Candlelight: Valentine's Day Special - Winter Park

 1300 S Denning Dr, Winter Park, FL 12 Feb 2026
CANDLELIGHT-CONCERTS

Fete Minuet: The Sequel 2026

 Winter Park Farmers' Market 18 Jan 2026
HEALTH-WELLNESS USD 30 TO 1,593

Candlelight: Best of Hip-Hop

 Mead Botanical Garden 22 Jan 2026
DANCE

Candlelight: Tribute to Adele

 Mead Botanical Garden 8 Jan 2026
CANDLELIGHT-CONCERTS

2026 Winter Park Fashion Week Show

 Full Sail Live 21 Feb 2026
FASHION USD 150 TO 1,069

Free for Seniors: Winter Park Scenic Boat Tour

 Scenic Boat Tour 14 Jan 2026
FREE

Fiddler's Green Charity 5K

 Mead Botanical Garden 21 Feb 2026
NONPROFIT

Glow With The Flow Annual Car Show

Dunkin' 24 Jan 2026
CAR-SHOWS

MamboYá Social

 The Trap 11 Jan 2026
WORKSHOPS

Girl Scout Father Daughter Dance

 St Margaret Mary Catholic Church 16 Jan 2026
FREE

NFL WILD CARD Sunday Watch Party at Aloma Cinema Grill in Winter Park!

 Aloma Cinema Grill 11 Jan 2026
ENTERTAINMENT FREE

More things to do in Winter Park

Festivals
Live Music
Food & Drinks
Pop-Ups
Halloween
Comedy
Carnivals
Music Festivals