2025 classic weekend events in Winter Park, FL

Fri, Sep 26, 6:00 PM

DeLand · City Sanctuary Church

Sat, Oct 4, 11:00 AM

Mercy Drive · Central Florida Fair

Tue, Sep 23, 9:00 AM + 4 more

Downtown Orlando · 101 S Garland Ave

Sat, Sep 27, 12:00 PM

Rouse Run · Boardwalk Bowl Entertainment Center

Wed, Feb 4, 7:00 AM

Sand Lake Commons · Rosen Plaza Hotel

Sun, Nov 9, 6:00 PM

Downtown Orlando · CityArts

Thu, Sep 25, 9:00 AM

Bay Lake · Disney's BoardWalk Resort

Fri, Nov 14, 10:00 AM

Florida Center · Dezerland Park Orlando

Sat, Sep 20, 10:00 AM

Downtown Orlando · Elixir Kitchen and Bar

Sat, Sep 20, 10:00 AM

Colonial Town Center · Orlando Executive Airport

Sun, Sep 28, 8:00 AM

Downtown Winter Park · Rollins College

Thu, Apr 16, 5:00 AM

Vista Way · WALT DISNEY WORLD® Resort

Fri, Sep 26, 9:00 PM

Downtown Orlando · Sessions

Sat, Oct 11, 7:00 PM + 1 more

Valdez · Cabana Live

Sat, Oct 18, 10:30 AM

Rose Isle · Harry P. Leu Gardens

Sat, Sep 20, 10:00 PM

Florida Center · RUMjungle

Wed, Nov 26, 10:00 PM

Florida Center · Rum Jungle

Saturday at 5:00 PM

Airport North · 6350 S Semoran Blvd

Sat, Sep 20, 8:00 PM

Winegard Road South · ME Theatre

Fri, Sep 26, 7:30 PM

Casselberry · Luxe Gala Venue