MARCH 20 – 22, 2026

WINTER PARK, FLORIDA

FRI & SAT 9am – 6pm
SUN 9am – 5pm

MARCH 21 – 23, 2025

WINTER PARK, FLORIDA

MARCH 20 – 22, 2026
WINTER PARK, FLORIDA

FRI & SAT 9am-6pm
SUN 9am-5pm

67th Winter Park Sidewalk Art Festival

Visit

the Festival

Exhibit

at the Festival

Volunteer

at the Festival

Friday Night Concert Headliner Announced!

Headlining the March 20th Friday night concert will be Saxophone great, Kim Waters, one of the premiere architects and reigning kings of Contemporary Jazz! 

Music starts Friday at 3:00 pm at the stage in North Central Park, and the Jazz Concert starts at 5:30 pm with a lead in band, followed by Kim Waters at 7:30 pm.

Best in Show

“Suburbandale”

R. Michael Wommack

Drawing & Pastels

“Music brings people together, fosters camaraderie and is needed to bring peace, joy and happiness in this world.”

Waters, one of the premiere architects and reigning kings of Contemporary Jazz, has written the soundtrack for the lives of generations of fans during his illustrious three-and-a-half decade a career. His instantly recognizable and gorgeous tone, captivating melodies, insatiable grooves and irresistible fusion of Jazz, R&B, Blues and Pop, have catapulted him to the top of the charts time and time again. The Maryland born and Georgia based saxman has performed with everyone from Al Green, Isaac Hayes and Patti LaBelle to Phyllis Hyman, Teddy Riley, Guy, and Gerald Albright, to name a few.

At the heart of Waters’ music and the real secret to his success, is his undying love affair with music. “My roots go back to the prettiest tones I’ve ever heard like Sonny Stitt, Cannonball Adderley, Charlie Parker, Stanley Turrentine and my friend Grover Washington Jr.,” says the Maryland born and Georgia resident. “For me, the saxophone is supposed to be romantic and beautiful. I’ll take a pretty tone and melody any day.”

Welcome

To Beautiful Park Avenue In Winter Park

The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor art festivals. The Festival debuted in March 1960 as a community project to bring local artists and art lovers together. It is produced by an all-volunteer board and draws more than 250,000 visitors each year.

Volunteer

Be A Part Of The Festival

By volunteering you will experience a one-of-a kind behind-the-scenes opportunity to gain a deeper appreciation for the artists and their award-winning artwork. Our volunteers help make the Winter Park Sidewalk Art Festival one of the top outdoor festivals in the country.

Patron

Support the Festival

Our Patrons Program was created to provide support of Festival artists through dedicated funds pledged to purchase artwork during our annual show. By participating, Patrons make monetary pledges for given levels of spending. The majority of your funds stay with you to purchase art and the remainder goes to support The Winter Park Sidewalk Art Festival.

 

Donate

Support Our Foundation

Since 1960, The Winter Park Sidewalk Art Festival has been a community leader in bringing art and the community together and has created wonderful memories for its visitors through the years. Donations to the foundation will help finance programs created to promote art appreciation and education through children’s programming at the annual Winter Park Sidewalk Art Festival, our scholarship programs at Rollins College and University of Central Florida and other community outreach programs throughout the year. 

Artists

2025 Categories And Artists

Clay

Digital Art

Drawing & Pastels

Emerging Artists

Fiber

Glass

Jewelry

Leather

Metal

Mixed Media 2D

Mixed Media 3D

Painting

Photography

Printmaking

Sculpture

Watercolor

Wood

2026 Featured Sponsors

Orlando Health - Jewett Orthopedic
Parks Lincoln
St. Pete Clearwater Visitors Bureau

Event

Information

Where:
In Central Park and Along Park Avenue in Winter Park, FL

Hours:
9 a.m. – 6 p.m., Friday and Saturday; 9 a.m. – 5 p.m., Sunday

Contact:
(407) 644-7207