Leonardtown, Maryland – The Leonardtown Business Association is hosting a themed weekend of community events under the banner “Fall in Love with Leonardtown,” combining First Friday celebrations on February 6, 2026, with the inaugural Love in Leonardtown Wedding Expo on Sunday, February 8, 2026, to draw visitors to downtown shops, restaurants, and vendors.
The weekend begins Friday, February 6, with Love in Leonardtown First Friday, running from 10 a.m. to 10 p.m. This extended event features shopping with special promotions, dining options, live entertainment, and the historic charm of downtown Leonardtown. Participants can stroll the streets, support local businesses, and experience the vibrant atmosphere that defines the town’s gatherings. First Fridays typically offer extended hours and themed activities to boost commerce and community engagement.
The highlight on Sunday, February 8, is the first-ever Love in Leonardtown Wedding Expo, scheduled from 12 p.m. to 3 p.m. Admission is free, and the event spans multiple venues including The Fenwick Inn, The Vault, and The Inn at Leonardtown. Attendees, particularly engaged couples and wedding planners, can connect with local vendors offering services such as venues, catering, photography, décor, and beauty options. The expo provides a centralized opportunity to explore wedding planning resources while promoting St. Mary’s County businesses.
Organized by the Leonardtown Business Association in partnership with the Town of Leonardtown and Visit St. Mary’s County, these events aim to showcase Leonardtown’s appeal as a destination for shopping, dining, and special occasions. The First Friday theme aligns with February’s focus on love and relationships, extending the typical monthly event format.
Weekend Itinerary
Friday, February 6th
- 9 am – 10 am Coffee Club with David McDonough at Edward Jones
- 10 am – 7 pm Visit the Old Jail Museum for a Free tour of this historic building
- 10 am – 7pm SOF Market’s “Fall in Love with Local” weekend sale
- 5 pm – 8 pm February First Friday opening reception “Let it Snow” at the St. Mary’s
County Arts Council - 5 pm – 8 pm North End Gallery’s February Invitational Event and reception
- 5:30 pm – 8 pm Live Music by Nightcap & Food by Dan D’s at Port of Leonardtown Winery
- 9 pm Join folks 21+ for the “Single and ready to Buck” at The Rex Theatre
- 9 pm to 1 am DJ Young & Shiesty take over Brudergarten
Saturday February 7th
- 10 am – 2 pm Book signing with science fiction writer T. J. Barlet at Fenwick Street Books
- 10 am – 5 pm Visit the Old Jail Museum and Visitor’s Center
- 10 am – 7pm SOF Market’s “Fall in Love with Local” weekend sale
- 2 pm to 5 pm Live Music by Wall Break & Food by Mouth of the Bay at Port of Leonardtown Winery
- 4 pm – 11 pm Prime Rib Saturday at Rucci’s
Sunday February 8th
- 10 am – 4 pm Book signing with children’s author Jennia D’Lima at Fenwick Street
Books. She will be signing her new book “Sunny and the Round Things” - 10 am – 5 pm Visit the Old Jail Museum and Visitor’s Center
- 11 am – 2 pm Balanced Paws Pet Care is having a “Smooch the Pooch” Valentine
themed pet photo booth benefiting local pets in need - 11 am – 5pm SOF Market’s “Fall in Love with Local” weekend sale
- 12 pm – 3 pm Love in Leonardtown Wedding Expo – The Fenwick Inn, The Vault & The Inn at Leonardtown
- 12 pm – 9 pm Sunday bucket $5.00 off special at Olde Town Pub
- 2 pm to 5 pm Live Music by Folk Salad & Food by Same Same But Different at Port of Leonardtown Winery
- 5pm – 9 pm Big Game Day at Leonardtown Cigars, Great Cigars, Great Drinks, Great Company
For the wedding expo, vendors showcase expertise in creating personalized celebrations, helping attendees translate ideas into actionable plans. The multi-venue setup allows exploration of distinct locations that could serve as wedding sites or inspiration sources.
More details on these and other happenings are available through the Visit Leonardtown MD events calendar at VisitLeonardtownMD.com. The site lists First Friday themes, including February 6 as Love in Leonardtown, and provides direct information on the wedding expo.
This weekend initiative supports local economic activity in Leonardtown, a Main Street Maryland community known for its historic downtown and community-driven events. By combining retail promotions with wedding-focused networking, organizers encourage both immediate patronage and long-term planning that benefits regional vendors.
The events reflect ongoing efforts by the Leonardtown Business Association to foster year-round vibrancy, with First Fridays occurring monthly and special themes rotating seasonally. February’s programming capitalizes on Valentine’s Day proximity to highlight romance-themed experiences in Southern Maryland’s St. Mary’s County.