Leonardtown

Getting there

By car Leonardtown is on Route 5 about 1.5 hours from Annapolis and 1 hour from Washington D.C. The Southern Maryland express can take visitors between the area and major airports nearby.

Getting around

Hillside Ride, ☏ +1 301 475-0065, [email protected]. Hillside Ride at Breton Bay is a premier, full valet with shuttle service, mobile advertisement company that uses Neighborhood Electric Vehicles (NEVs) $5 donation to ride all day. Small children ride free.

See

Leonardtown has a vibrant arts and entertainment district, home to a music school, art galleries, a chocolatier, a painting studio, and shops for antiques and flowers.

Do

Port of Leonardtown Public Park, ☏ +1 301 475-9791, fax: +1 301 475-5350, [email protected]. A little known, secret hidden along the McIntosh Run in Leonardtown is the Port of Leonardtown Public Park. This developing passive park and winery is the launch point of a nearly 3-mile, serene canoe/kayak trail. As you paddle along the McIntosh Run you will pass through a 58-acre Forest Interior Dwelling Species Habitat. This area is home to bald eagle families, Baltimore Orioles, wild turkeys and many other bird species. The trail terminates at the Leonardtown Wharf Public Park. Bring a picnic lunch or stroll up to Leonardtown Square and enjoy lunch at a restaurant.

Buy

The local Amish communities have auctions where they sell crafts like quilts.

Shepard's Old Field Market (SOF Market), 22725 Duke St, ☏ +12403094067. 10AM-7PM (5PM on Sundays, closed M). A local shopping mall with 90 shops, ranging from handmade soaps (Barclay Soap Co.) to hairdressers (Old Towne Barbershop). (updated Oct 2025)

Eat

The Slice House, 22745 Washington St, ☏ +1 301 997-6577. Pizza restaurant. (updated Dec 2024)

Drink & nightlife

Port of Leonardtown Winery, 23190 Newtowne Neck Road, ☏ +1 301 690-2192. Daily noon-6PM. A cooperative winery that sources its grapes from a dozen vineyards in Southern and Eastern Maryland. (updated May 2019) Old Towne Pub, 22785 Washington St, ☏ +1 301 475-8184. (updated May 2019)

Sleep

Executive Inn & Suite Park Avenue Hotel, 41655 Park Ave, ☏ +1 301 475-3000, fax: +1 301 475-3002. Check-in: 2PM, check-out: 11AM. Fitness center, sauna, bar & cafe/lounge, continental breakfast, business center, 100% non-smoking.