Festivals & Annual Events in Winter Park, FL (2026)

Looking for the festivals & annual events near you in Winter Park? Here are 7 festivals and annual events worth the trip, starting with Winter Park Sidewalk Art Festival and Winter Park Autumn Art Festival, with what each one does best and how to get there.

7 picks · Updated October 2026

1
Winter Park Sidewalk Art Festival

Event in Park Avenue
Running since 1960, this juried art show fills Central Park and Park Avenue on the third weekend of March and draws more than 250,000 visitors. Friday evening brings a headline concert in the park.
- Art festival
- Festival
- Spring
- Outdoor
Call Winter Park Sidewalk Art Festival Website for Winter Park Sidewalk Art Festival (opens in a new tab)Directions to Winter Park Sidewalk Art Festival (opens maps)
2
Winter Park Autumn Art Festival

Event in Park Avenue
A free November weekend art show in Central Park and along Park Avenue featuring only Florida artists, with a children's art workshop and a beer garden.
- Art festival
- Festival
- Fall
- Free
Website for Winter Park Autumn Art Festival (opens in a new tab)Directions to Winter Park Autumn Art Festival (opens maps)
3
Winter Park Paint Out

Event
A week-long plein air festival each April based at the Albin Polasek Museum, where more than 20 artists paint outdoors. Demos are free, and the finished works are for sale.
- Art festival
- Festival
- Spring
- Free
Website for Winter Park Paint Out (opens in a new tab)Directions to Winter Park Paint Out (opens maps)
4
Winter on the Avenue

Event in Park Avenue
A free early December evening on Park Avenue with tree and menorah lighting, snow slides, s'mores and an outdoor holiday movie.
- Christmas
- Free
- Outdoor
- Family
Website for Winter on the Avenue (opens in a new tab)Directions to Winter on the Avenue (opens maps)
5
Winter Park 4th of July Celebration

Event in Park Avenue
A free small-town Independence Day evening in Central Park with a choir and brass concert, a children's bike parade and free pie and ice cream while supplies last.
- Summer
- Festival
- Parade
- Free
Website for Winter Park 4th of July Celebration (opens in a new tab)Directions to Winter Park 4th of July Celebration (opens maps)
6
Winter Park Christmas Parade

Event in Park Avenue
Billed as Central Florida's oldest continuous holiday parade, it travels down Park Avenue on the first Saturday of December with 80-plus groups.
- Christmas
- Parade
- Outdoor
- Family
Website for Winter Park Christmas Parade (opens in a new tab)Directions to Winter Park Christmas Parade (opens maps)
7
Christmas in the Park (Winter Park)

Event in Park Avenue
One evening in early December when the Morse Museum lights Tiffany windows in Central Park and the Bach Festival Choir performs.
- Christmas
- Outdoor
- Family
- Local favorite
Website for Christmas in the Park (Winter Park) (opens in a new tab)Directions to Christmas in the Park (Winter Park) (opens maps)

Orlando's festival calendar by season

Winter and spring are the busiest festival months. The ZORA! Festival peaks in late January, the Central Florida Fair arrives in late February or early March, and the Winter Park Sidewalk Art Festival takes the third weekend of March. April brings the Florida Film Festival and the Winter Park Paint Out, and Orlando Fringe runs for about two weeks in May. Summer is quieter, with July 4 fireworks at Lake Eola and in Winter Park. Fall picks back up with Come Out With Pride in October, Fiesta in the Park and the Winter Park Autumn Art Festival in November, then a run of holiday events into January.

About this list

Every place here is a locally run business in Orange County with its own website, which we checked for hours, menus and contact details. We leave national chains off our best-of lists and favor places with a clear specialty.

This page covers 7 festivals and annual events 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.

About Winter Park

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.

Frequently asked questions

What are the biggest festivals in Winter Park?

The Winter Park Sidewalk Art Festival draws more than 250,000 visitors each March, and the Central Florida Fair runs about 11 days in late winter. Come Out With Pride, Orlando Fringe and the Florida Film Festival are other major annual events.

What festivals are in Winter Park in the spring?

Spring brings the Winter Park Sidewalk Art Festival in March, the Florida Film Festival and Winter Park Paint Out in April, and Orlando Fringe in May. Fiesta in the Park also holds a spring weekend around Lake Eola. Check each official page for this year's dates.

Are there free festivals in Winter Park?

Yes. Come Out With Pride, the Winter Park Autumn Art Festival, Winter on the Avenue and the Winter Park 4th of July Celebration are free. Orlando Fringe has a free outdoor stage and Kids Fringe, and the ZORA! Festival is free on Friday with kids free all weekend.

When is the Winter Park Sidewalk Art Festival?

The festival is held on the third weekend of March each year in Central Park and along Park Avenue. It runs Friday through Sunday, with a headline concert on Friday evening.

When is Winter Park Pride?

Come Out With Pride Orlando is held on a Saturday in October at Lake Eola Park, with a festival during the day, a downtown parade in the late afternoon and fireworks at night. Check the official page for this year's date.