Highwaymen Heritage Trail Festival

The 9th Annual Highwaymen Heritage Trail Art Show and Festival 

The City of Fort Pierce is excited to announce the 9th Annual Highwaymen Heritage Trail Art Show & Festival, a vibrant celebration honoring the world-renowned Florida Highwaymen Artists and their significant contributions to the cultural heritage of Fort Pierce.

The event will take place on Saturday, February 21, 2026, 10:00 AM to 3:00 PM, at Moore’s Creek Linear Park, located at 435 N 7th Street, at the corner of Avenue D and 7th Street in the historic Lincoln Park neighborhood. This free event serves as a tribute to the birthplace of the Highwaymen Artists, who have been credited with sparking the “Last Great American Art Movement of the 20th Century.”

The festival will feature:

• Original and 2nd Generation Highwaymen Artists showcasing and selling their artwork.
• Tribute booths honoring artists who are no longer with us.
• Displays by regional artists and arts organizations.
• Live jazz music, a variety of food and novelty vendors, and a fun-filled Kid’s Zone.

If you are interested in a tour of the Highwaymen Heritage Trail, please register here:  Highwaymen Heritage Trail Tour 2026

The Heritage Trail tour is so popular that all slots are full! —Registration is closed. 

About the Highwaymen

If you traveled Florida Route 1 in the 1960s, you may have encountered young African American artists selling beautifully painted Florida landscapes from the trunks of their cars along the side of the road. Jim Crowe segregation prevented the painters from entering galleries – so they sold their works at motels, businesses, and to tourists – for $15-$25. It is estimated that they created and sold more than 200,000 paintings by the end of the 20^th century.

Many of the young painters were inspired and mentored by Fort Pierce’s world-renowned landscape artist Albert Earnest “Bean” Backus, creator of richly detailed depictions of “Old Florida” scenery. Encouragement from Backus, Lincoln Park Academy art teacher Zanobia Jefferson, and each other helped propel the young entrepreneurs to paint their way out of picking citrus and tomatoes, using wallboard as their canvas and crown molding for frames.

The loosely associated group of twenty-five men and one woman came to be known as The Highwaymen. Mostly from Fort Pierce, the artists were inducted into the Florida Artists Hall of Fame in 2004.

We hope you will join us for our next Highwaymen Heritage Trail Art Show/Sale and Festival to celebrate the world-renowned Highwaymen artists and enjoy the rich cultural history of Fort Pierce, one of the oldest cities on Florida’s east coast. Visit About the Highwaymen Heritage Trail for information on the award-winning Highwaymen Heritage Trail.