Upcoming Live Music Events

Rick Braun with special guest Randy Jacobs

 Blue Bamboo Center For The Arts 3 May 2026
MUSIC

Winter Park Sidewalk Art Festival Celebration

 445 N Park Ave, Winter Park, FL, United States, Florida 32789 20 Mar 2026
FESTIVALS

Candlelight: Tribute to Taylor Swift

 Mead Botanical Garden 9 Apr 2026
CANDLELIGHT-CONCERTS

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Upcoming Food & Drinks Events

Taste of Winter Park

 Winter Park Farmers' Market Venue 1 Apr 2026
MUSIC USD 55 TO 384

Rollins Men’s Soccer Elite Overnight Camps 2026

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

2026 Unleashed. Uncorked.Unframed. Gala

 Winter Park Events Center 16 May 2026
FOOD-DRINKS USD 300 TO 3,500

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Upcoming Festivals Events

The 67th Winter Park Sidewalk Art Festival

 Park Avenue, Winter Park 20 Mar 2026
ART

1st Annual Holler Ford Racing Showcase

 1875 South Orlando Avenue, Maitland, FL, United States, Florida 32751 14 Mar 2026
CAR-SHOWS

Smile Mile - Kids Run

 Blue Jacket Park 14 Mar 2026
KIDS

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Upcoming Pop-Ups Events

Orlando Local Makers at Foxtail Coffee Winter Park!

 Foxtail Coffee (Winter Park, FL) 5 Apr 2026
POP-UPS

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

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

Romancing the Books Festival 2026 | Keynote: Meryl Wilsner

 Winter Park Library 28 Mar 2026
ART FREE

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Upcoming Easter Events

An Action Church Easter - Winter Park

 Action Church Winter Park 3 Apr 2026
EASTER FREE

Winter Park Village Easter Bunny & Sidewalk Sale

 Winter Park Village 4 Apr 2026
EASTER-BUNNY

Easter Brunch at The Alfond Inn

 The Alfond Inn at Rollins College 5 Apr 2026
EASTER-EGG-HUNT USD 0 TO 164

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Upcoming Comedy Events

The Religious Right Is Fighting a Holy War. Here's Our Plan To Win.

 University Club of Winter Park 19 Apr 2026
ENTERTAINMENT

Betsy Ross & Friends: History as It Never Happened

 Schaeffer Hall at St. John Church 11 Apr 2026
HEALTH-WELLNESS

Solomon Jaye | April 25 | Blue Bamboo

 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 25 Apr 2026
ART

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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

Free: Jazz Festival—Live with The Yo Cats

 Winter Park Events Center 26 Mar 2026
MUSIC FREE

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Trending Events in Winter Park

RLC & CJP Spring Fling

 Redeemer Lutheran Church 4 Apr 2026
ART

Toddler Meetup: Easter Egg Hunt & Picnic Lunch

 Mead Botanical Garden 31 Mar 2026
EASTER-EGG-HUNT

AdventHealth Winter Park Road Race 10k and 2 Mile

 Park Avenue Central Park 28 Mar 2026
SPORTS

The Great Duck Derby

 Mead Botanical Garden 28 Mar 2026
SPORTS FREE

American Maestro: The Music of John Williams

 Calvary Orlando 22 May 2026
ENTERTAINMENT

Mark This Moment Presented by Rollins FCA

 Alfond Sports Center 13 Apr 2026
USD 0 TO 5,000

Ricky Sylvia & The Buzzcatz present: Crooners and Cool Cats

 Blue Bamboo Center For The Arts 10 May 2026
MUSIC

Rollins Summer Volleyball Camps 2026

 Alfond Sports Center 11 May 2026
SPORTS USD 164 TO 487

80s Dance Party Orlando!

 6700 Aloma Ave, Winter Park, FL 32792, United States 20 Mar 2026
ENTERTAINMENT

Candlelight: Queen vs. ABBA Tribute

 Mead Botanical Garden 11 Mar 2026
CANDLELIGHT-CONCERTS

Daniela & Nate Love & Bossa Nova | April 3 | Blue Bamboo

 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 3 Apr 2026
MUSIC

Mac Sabbath

 Conduit 10 Apr 2026
TRIPS-ADVENTURES

Bonsai & Cheers -Forward/Slash - L&J Nursery - Barbados Cherry

 Forward Slash Distillery & Blending House 9 Apr 2026
WORKSHOPS USD 75

Cody McCafferty Trio | March 20 | Blue Bamboo

 460 E. New England Ave., Winter Park, FL, United States, Florida 32789 20 Mar 2026
ENTERTAINMENT

Ladies’ Floral Dress Spring Brunch (Winter Park)

 AVA MediterrAegean Winter Park 15 Mar 2026
BRUNCH

More things to do in Winter Park

Live Music
Food & Drinks
Festivals
Pop-Ups
Easter
Comedy
Easter Egg Hunt
St. Patrick's Day
Carnivals
Music Festivals