Fall in Love with Leonardtown This Weekend

Leonardtown, MD — The Leonardtown Business Association invites the community to Fall in Love with Leonardtown during a weekend filled with charm, celebration, and local flair.

The festivities kick off with First Friday, featuring a full day of fun throughout town. Visitors can enjoy extended shopping hours, special promotions, delicious dining, live entertainment, and the welcoming atmosphere that makes Leonardtown such a special place to gather. It’s the perfect opportunity to stroll the streets, support local businesses, and soak in the vibrant energy of downtown.

The weekend wraps up with the Love in Leonardtown Wedding Expo, a must-attend event for newly engaged couples and anyone planning a wedding or special celebration. Attendees will meet talented local vendors showcasing stunning venues, catering, photography, décor, beauty services, and more—all in one place. It’s an inspiring way to turn wedding dreams into reality while supporting local businesses.

Whether you’re shopping, dining, celebrating love, or planning your forever, this weekend offers something for everyone. Come experience the heart of our community and see why there’s always a reason to fall in love with Leonardtown.

For more information on events and upcoming happenings, visit VisitLeonardtownMD.com events calendar.

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 7 th
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 8 th
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