The Leonardtown Business Association launches its March Madness First Friday event March 6 through 8, 2026, in historic Leonardtown, St. Mary’s County, transforming the downtown area into a hub of themed promotions, extended shopping hours, live entertainment, and community activities inspired by the NCAA basketball tournament’s high-energy spirit.
This monthly First Friday series, held year-round, spotlights local businesses with specials, discounts, and unique experiences. For March, dubbed March Madness, the event extends beyond the traditional Friday evening to fill the full weekend, encouraging residents and visitors to explore shops, galleries, restaurants, and attractions while supporting small businesses in Southern Maryland’s charming county seat.
Participating businesses offer exclusive deals, themed treats, and in-store happenings, many carrying promotions through Sunday to maximize weekend foot traffic.
Highlights kick off Friday, March 6:
- 9 a.m. to 10 a.m.: Coffee Club with David McDonough at Edward Jones.
- 10 a.m. to 7 p.m.: Free tours of the Old Jail Museum, a historic site showcasing local heritage.
- 10 a.m. to 7 p.m.: Shepherd’s Old Field Market hosts “Lucky Sales” throughout the weekend.
- 12 p.m.: Ribbon cutting ceremony at The Vintage Collective.
- 5 p.m. to 7:30 p.m.: Free First Friday art activity led by Jami from Elsewise Art.
- 5 p.m. to 8 p.m.: Opening reception for “Youth Art Month” at the St. Mary’s County Arts Council, featuring local artist Tanya from Bubbles Bzzz pottery café in Lexington Park.
- 5 p.m. to 8 p.m.: North End Gallery presents “All Creatures Great and Small” exhibition.
- 5:30 p.m.: Live music by Matt Guilherme at Port of Leonardtown Winery, with Heidi’s Eats and Sages Treats food trucks on site.
Saturday, March 7, continues the momentum:
- 10 a.m. to 5 p.m.: Free Old Jail Museum tours.
- 10 a.m. to 6 p.m.: Grand opening of The Vintage Collective, featuring retro treasures and timeless finds.
- 10 a.m. to 7 p.m.: Shepherd’s Old Field Market “Lucky Sales.”
- 2 p.m. to 5 p.m.: Live music by Wildgood Duo at Port of Leonardtown Winery, paired with Cousin’s Maine Lobster food truck.
- 4 p.m. to 11 p.m.: Prime Rib Saturday special at Rucci’s.
- 8 p.m.: Love, Hate and Mixtape show at the Rex Theatre, free entry for ages 21 and older.
Sunday, March 8, wraps the weekend:
- 10 a.m. to 5 p.m.: Free Old Jail Museum tours.
- 11 a.m. to 3 p.m.: Racecar Car Show at Leonardtown Ford.
- 11 a.m. to 5 p.m.: Shepherd’s Old Field Market “Lucky Sales.”
- 12 p.m. to 9 p.m.: $5 off Sunday bucket special at Olde Town Pub.
- 2 p.m. to 5 p.m.: Live music by Chris Beard at Port of Leonardtown Winery, with Nick’s DC Pizza food truck.
The Leonardtown Business Association organizes the series in partnership with the Town of Leonardtown, aligning with the community’s emphasis on historic preservation, arts, and economic vitality in St. Mary’s County. First Fridays occur monthly, with themed weekends from May through October, but March’s bracket-style excitement draws crowds to downtown’s walkable streets lined with galleries, eateries, and boutiques.
For the latest details, including a complete list of participating businesses and current specials, check VisitLeonardtownMD.com or follow Leonardtown – A Most Exceptional Place on social media.
This event provides an accessible way to engage with Southern Maryland’s local economy and culture amid the broader March Madness season.
