Leonardtown will welcome visitors this weekend with a lively mix of vintage shopping, Star Wars-themed activities, live music and family-friendly events during the May First Friday celebration.
The three-day event, running Friday through Sunday, May 1-3, transforms the historic St. Mary’s County town into a hub of shopping, entertainment and community gatherings. Organizers encourage residents and visitors alike to shop local, stroll the streets and enjoy the spring atmosphere.
Friday activities begin early and continue into the evening. Popcorn Friday returns at Sneade’s from 10 a.m. to 2 p.m. The Old Jail Museum will extend its hours from 10 a.m. to 7 p.m. A free butterfly craft session is scheduled for 5 p.m. to 7 p.m., while art show openings and the Butterfly Trail launch run from 5 p.m. to 8 p.m.
Live music fills the downtown square at 6 p.m. with performer Jack Allen. A drum circle with SoMar Drummers starts at 5 p.m. on SoMar Drive. The Leonardtown trolley will operate from 5 p.m. to 10 p.m. to help visitors get around town. Music bingo at Leonardtown Cigars, live music at Brudergarten and sets at Action Lounge and The Rex round out the evening entertainment. The Spring Festival at the fairgrounds runs from 5 p.m. to 10 p.m.
Saturday features Star Wars Weekend fun at participating businesses throughout the day. A vendor market and yard sale takes place at the Town Market from 9 a.m. to 4 p.m., while the Arts Council hosts a sidewalk sale from 11 a.m. to 3 p.m. The Spring Festival continues from 10 a.m. to 10 p.m. Evening options include a bath meditation at 6:30 p.m., karaoke at Action Lounge and live music at Brudergarten.
Sunday offers a relaxed close to the weekend. Fenwick Street Used Books hosts a book signing from 10 a.m. to 5 p.m. The Spring Festival runs from 10 a.m. to 6 p.m. Free games are available at Action Lounge from noon to 8 p.m., with bucket specials at Olde Town Pub from noon to 9 p.m. Families can enjoy free skating from 2 p.m. to 5 p.m. at Leonard Hall Recreation Center.
The weekend blends vintage shopping vibes with family entertainment, live performances and themed activities. Whether visitors seek unique finds at yard sales and markets, Star Wars adventures or simply a chance to enjoy live music and good food, Leonardtown provides plenty of options.
The trolley service on Friday makes downtown exploration easy and convenient. Organizers note that supporting local businesses helps sustain the vibrant community atmosphere that makes Leonardtown a destination in Southern Maryland.
Complete details and updates are available on the Visit Leonardtown website at VisitLeonardtownMD.com/eventscalendar.
