Winter Park Festivals Events

The 67th Winter Park Sidewalk Art Festival

Park Avenue, Winter Park 20 Mar 2026

Taste of Winter Park

Winter Park Farmers' Market Venue 1 Apr 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

Silver Screen Classics

Knowles Memorial Chapel 25 Apr 2026

Silver Screen Classics

Knowles Memorial Chapel 26 Apr 2026

Sacred Service Duke Ellington with Samuel McKelton

Knowles Memorial Chapel 10 Apr 2026

Free: Jazz Festival—Live with The Yo Cats

Winter Park Events Center 26 Mar 2026

Lysander Piano Trio

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

Live Painting at George's Cafe in Winter Park

George's Cafe in Winter Park 21 Mar 2026

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

Winter Park Events Center 17 Apr 2026

Romancing the Books Festival 2026 | Keynote: Meryl Wilsner

Winter Park Library 28 Mar 2026

The Community Market

Agape Hall 17 May 2026

Arankai at Conduit

Conduit 20 May 2026

Auditions: A Midsummer Night's Dream by William Shakespeare

6900 Aloma Avenue , Winter Park, FL, United States, Florida 32792 28 Mar 2026