Winter Park Festivals Events

Taste of Winter Park

Winter Park Farmers' Market Venue 1 Apr 2026

1st Annual Holler Ford Racing Showcase

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

Smile Mile - Kids Run

Blue Jacket Park 14 Mar 2026

The Great Duck Derby

Mead Botanical Garden 28 Mar 2026

Winter Park Sidewalk Art Festival Celebration

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

Age of Enlightenment: Haydn, Mozart, Beethoven

Knowles Memorial Chapel 22 Feb 2026

St. John Passion | J.S. Bach

Knowles Memorial Chapel 1 Mar 2026

Silver Screen Classics

Knowles Memorial Chapel 25 Apr 2026

Modern Nurse Fest Florida

Winter Park Community Center 24 Feb 2026

Sacred Service Duke Ellington with Samuel McKelton

Knowles Memorial Chapel 10 Apr 2026

Silver Screen Classics

Knowles Memorial Chapel 26 Apr 2026

Free: Jazz Festival—Live with The Yo Cats

Winter Park Events Center 26 Mar 2026

25th Annual Orange Blossom Jubilee "Under the Big Top"

Winter Park Events Center 17 Apr 2026

The 67th Winter Park Sidewalk Art Festival

Park Avenue, Winter Park 20 Mar 2026

Cheryl & The Usual Suspects @ Fiddler's Green!

Fiddlers Green Irish Pub & Eatery 22 Feb 2026

Fuoco Obbligato

Tiedtke Concert Hall | 1000 Holt Ave, Winter Park, FL 32789-4499, United States 28 Feb 2026

Lysander Piano Trio

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