Highwaymen Heritage Trail Festival

5th Annual Highwaymen Heritage Trail Art Show and Festival Set for February 15, 2020

Join us Saturday, February 15th from 10am-4pm for the Highwaymen Heritage Trail Art Show/Sale and Festival, along beautiful Moore’s Creek Linear Park at the corner of 8th Street and Avenue D in Fort Pierce.

The annual Art Show/Sale and Festival will feature many of the “Original” and “2nd Generation” Highwaymen artists, FREE guided Highwaymen Heritage Trail tours, live jazz music, local cuisine, a Kid’s Zone and large walk-thru exhibit of 5th grade entries into the 2020 Highwaymen Art Contest.

The event is FREE. Guided Trail tour seating is limited. Please call 772-467-3183 to reserve your seat(s).

Vendor space is also FREE. Just fill out and return your application by February 1, 2020 (See "Forms" section).


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 apiece. It is estimated that they created and sold more than 200,000 paintings by the end of the 20th century.

Many of the young painters were inspired and mentored by Fort Pierce’s world-renown 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 on Saturday, February 15, 2020, for the Highwaymen Heritage Trail Art Show/Sale and Festival to celebrate the world-renown Highwaymen artists and enjoy the rich cultural history of Fort Pierce, one of the oldest cities on Florida’s east coast. Visit The Highwaymen Trail website for information on the lives and times of the Highwaymen artists and the award-winning Highwaymen Heritage Trail.

Stop 10
Highwaymen Street Banner