Leonardtown Art Walk

Annual Arts & Entertainment Celebration

St. Mary’s County Arts Council and the Town of Leonardtown host an annual Art Walk every September. This event celebrates Leonardtown’s Arts & Entertainment District designation.

Local artists submit their work for display in businesses in the downtown Leonardtown area. The Art Walk contest is an exciting opportunity to view work across a wide range of media and styles, with generous prizes for the winners!

Stop by any of the businesses on the map during September, pick up a ballot, get the ballot stamped at three different locations, and select your three favorite pieces of art! You can select art from ANY of the businesses as long as you visit at least three different locations.

Opening Reception: First Friday, September 4, 2026, from 5-8 PM at St. Mary’s County Arts Council

Contest/Exhibit Run Dates: September 2026

Contest Prizes: First place - $100 Cash Prize, Second Place - $75 Gift Card for a local shop (TBA), Third Place - $50 Gift Card for a local shop (TBA)!

We also have gift cards for two lucky voters, drawn at random!

Are you an artist interested in being part of the Art Walk event? See the Call for Art button below!

Are you a business located in the Leonardtown Arts & Entertainment District? See the button below to sign up to host a piece of art!

Benefits include your business listed on the Art Walk map and ballot, increased foot traffic/visitors, and beautiful art displayed for the month of September! A donation of $25 per business is kindly requested to support this event. A link is on the sign up form.