LEONARDTOWN, Md. — The 7th Annual Scarecrow Stroll returned to downtown Leonardtown on Friday. The creative tradition invites residents, businesses, nonprofits and local groups to design and display scarecrows all around town, turning sidewalks, storefronts and public spaces into a festive fall gallery.
The Scarecrow Stroll, organized by the Leonardtown Business Association (LBA), has become a seasonal tradition, adding color and charm to the downtown square while showcasing the creativity of local businesses, organizations and families. Originally launched in the 2010s, the Scarecrow Stroll has steadily grown in popularity and evolved into one of Leonardtown’s anticipated autumn attractions.
Visitors can explore displays throughout downtown, scan QR codes posted beside each scarecrow and cast votes for their favorite scarecrows across multiple categories. Voting runs through Oct. 27, with winners announced at the end of the month.
The stroll is free and open to all, offering an opportunity for families to enjoy Leonardtown’s dining, shopping and cultural attractions while celebrating the fall season.
Among this year’s participants, Nick Colvin has entered the contest for his third year. His display was inspired by the 1979 science-fiction movie “Alien” and features Ellen Ripley battling the menacing face-huggers from the film.
“I hope people enjoy it, and just, you know, get a good laugh or get some good pictures and have a great time,” Colvin said. “Hope I get some votes! But no matter what, it’s so much fun just to be able to participate.”
At the St. Mary’s County Arts Council Gallery and Gift Shop, Gallery Manager Melanie Dichter said this was her first year taking part in the Scarecrow Stroll. She created the Arts Council’s entry, pulling together supplies and a quick design with the help of Executive Director Susie Glauner.
“My boss asked how I would like to put together the scarecrow this year,” Dichter said. “I painted a picture for it and built what we called Bob, our artist. We both had the same vision of a stereotypical artist with a painting scene. It came together fast, but it was a lot of fun to create.”
For many longtime residents, the Scarecrow Stroll represents a part of what makes Leonardtown home. Tim and Brenda Moore moved to Southern Maryland 15 years ago and say it’s the small-town traditions that made them stay.
“We’re not originally from here,” Tim said. “We’ve lived here 15 years, but we really like the town because of all the activities they have all the time.”
On Saturday morning, the Moores had just finished taking part in the Walk for the Poor at St. Aloysius Catholic Church before strolling through town to see the scarecrow displays.
“We were walking through town and saw the scarecrows,” Brenda said. “There’s just so much creativity. Like the one with a pumpkin heart, or the Golden Girls over there. Every weekend there’s something new going on in Leonardtown.”
The Moores, both originally from Pennsylvania, said they’ve watched Leonardtown evolve since they arrived in 2010 — from the revitalization of the Wharf and downtown to the steady growth of community events that keep the town lively year-round.
“It’s just a nice town to come and walk around for no purpose other than to walk around,” Tim said. “There’s always people around, always something interesting.”
Moore explained that it’s simple things, like seeing families stop for photos beside handmade scarecrows, that remind them why they chose to settle in Leonardtown.
Five Fast Facts About The Leonardtown Scarecrow Stroll
Dates: Oct. 3–31
Location: Leonardtown, Md. — Scarecrows will be exhibited throughout Leonardtown’s walkable downtown district (along Washington Street, Fenwick Street and surrounding blocks)
Voting window: The public is invited to vote for their favorites Oct. 3–27
Organizer: Leonardtown Business Association (LBA)
History: 2025 marks the 7th Annual Scarecrow Stroll
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