Highwaymen Heritage Trail Festival

6th Annual Highwaymen Heritage Trail Art Show and Festival for February 2022 is CANCELLED

In the consideration of health and safety of everyone, the City wants to minimize any potential risk to our community.  We sincerely apologize for any inconvenience this may have caused and kindly ask for your understanding. The Highwaymen Festival is one of our biggest events. As many were looking forward to having a great time celebrating and honoring the original Highwaymen and 2nd generation artist along with much more. We are very disappointed that we must make this sudden change. We will plan a new date for the event once operations return to normal.


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 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 for our next 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


Vendor Forms:

Volunteer Forms:

Festival Flyer: