Seasonal Events & Festivals near me in Winter Park, FL
7 seasonal events & festivals in Winter Park, Florida, each with a direct link, phone number and what they offer. Orlando's calendar is packed with annual events, and many of the best ones only happen for a few weeks a year.
7 listings ยท Updated October 2026
Seasonal Events & Festivals listings
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Winter Park Sidewalk Art Festival
Event in Park Avenue
Running since 1960, this volunteer-led juried art show fills Central Park and Park Avenue each March, drawing more than 250,000 visitors.
- Art festival
- Festival
- Spring
- Outdoor
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Winter on the Avenue
Event in Park Avenue
The Winter Park Chamber's free holiday kickoff lights the tree and menorah on Park Avenue, then fills Central Park with snow slides, s'mores and an outdoor family movie.
- Christmas
- Free
- Outdoor
- Family
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Winter Park 4th of July Celebration
Event in Park Avenue
Winter Park's free, small-town style Independence Day evening in Central Park mixes patriotic music with a decorated children's bike parade and a kids' zone. Local sponsors hand out pie, cake and ice cream while they last.
- Summer
- Festival
- Parade
- Free
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Winter Park Autumn Art Festival
Event in Park Avenue
Hosted by the Winter Park Chamber of Commerce, this free weekend art show in Central Park and along Park Avenue features only Florida artists working in media from ceramics to photography.
- Art festival
- Festival
- Fall
- Free
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Winter Park Christmas Parade
Event in Park Avenue
Organized by the Winter Park Chamber of Commerce, this morning parade travels down Park Avenue on the first Saturday of December and is billed as Central Florida's oldest continuous holiday parade.
- Christmas
- Parade
- Outdoor
- Family
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Christmas in the Park (Winter Park)
Event in Park Avenue
The Morse Museum opens Winter Park's holiday season by displaying lit Tiffany stained-glass windows in Central Park for one evening. The Bach Festival Choir and Brass Ensemble perform a holiday concert alongside them.
- Christmas
- Outdoor
- Family
- Local favorite
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Winter Park Paint Out
Event
A week-long plein air festival based at the Albin Polasek Museum, where more than twenty professional artists paint outdoors around Winter Park and Orlando.
- Art festival
- Festival
- Spring
- Free
Seasonal Events & Festivals in Winter Park: what we found
This page covers 7 seasonal events & festivals in Winter Park. You'll find them in Park Avenue.
What comes up again and again on their menus and websites: Bach Festival Choir and Brass Ensemble concert.
Winter Park sits just north of Orlando and is known for Park Avenue, Rollins College, its chain of lakes and brick streets. The city has a dense cluster of independent restaurants, boutiques, salons and professional offices.
How to choose a event near Winter Park
Orlando's calendar is packed with annual events, and many of the best ones only happen for a few weeks a year. Fall brings Halloween Horror Nights at Universal, Howl-O-Scream at SeaWorld and Mickey's Not-So-Scary Halloween Party at Magic Kingdom, along with pumpkin patches, corn mazes and the EPCOT International Food & Wine Festival. The holiday season adds light displays such as Dazzling Nights at Leu Gardens and the Lake Eola tree show, plus Disney and Universal holiday events and Winter Park's free parade and tree lighting. Winter and spring are festival season, with the ZORA! Festival in Eatonville, the Central Florida Fair, the Winter Park Sidewalk Art Festival, EPCOT's arts and flower festivals, the Florida Film Festival and Orlando Fringe. Summer is quieter, with July 4 fireworks and SeaWorld's Electric Ocean nights. Some events are free, some are included with park admission and some need their own ticket, so read each listing carefully. Dates change every year, so always confirm this year's schedule on the official event page before you make plans.
Local tip
Separately ticketed theme park parties like Mickey's Not-So-Scary Halloween Party can sell out well in advance, and all of its 2026 dates are already sold out, so watch for ticket releases early if a party is on your list.
Frequently asked questions
What seasonal events are included with theme park admission?
Several are. The EPCOT International Food & Wine Festival, Festival of the Holidays, Flower & Garden Festival and Festival of the Arts are included with EPCOT admission. SeaWorld's Christmas Celebration and Seven Seas Food Festival are included with park admission, though festival food costs extra. Halloween Horror Nights, Howl-O-Scream and Disney's after-hours parties need their own tickets.
What are the best fall events in Orlando?
Halloween Horror Nights, Howl-O-Scream and Mickey's Not-So-Scary Halloween Party are the big theme park events. Locally, Come Out With Pride fills Lake Eola Park in October, Club Lake Fall Festival and Painted Oaks Academy run pumpkin patches, and Fiesta in the Park and the Winter Park Autumn Art Festival take place in November.
What free seasonal events are there in Orlando?
Come Out With Pride, Winter on the Avenue, the Winter Park Christmas Parade, Christmas in the Park, the Winter Park Autumn Art Festival and the Winter Park 4th of July Celebration are free. The Lake Eola Christmas tree runs free nightly light shows after the city's tree lighting in early December.
When is the Central Florida Fair?
The Central Florida Fair runs for about 11 days in late February or early March at the fairgrounds on West Colonial Drive. Check the fair's official site for this year's dates.
What events happen at Universal in the spring?
Universal Orlando Mardi Gras runs on select nights in late winter and spring, with a nighttime parade where riders toss beads, concerts on select nights and festival food around Universal Studios Florida.
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