Leonardtown Area

Leonardtown, Compton Bayside, Redgate, Chingville, Callaway, Clements

Click Above to See a Panoramic Tour of Beautiful Historic Leonardtown

Centrally located, Leonardtown serves as a convenient hub. | Shopping, dining, a winery, a quaint town square and a water trail along Breton Bay offer fun for all ages. Newtowne Neck State Park is not far from the town at the end of Route 243. The park offers opportunities for paddling Breton Bay and the Potomac River, as well as for hiking, birding, and hunting. Adjacent to the park is St. Francis Xavier Church which is part of the Religious Freedom National Scenic Byway.

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Town of Leonardtown

Leonardtown received its moniker “a most convenient place” back in the early 18th century. The county’s courthouse, hospital, and governmental center are located here. Shops, galleries, and restaurants are located around the quaint town square and along Fenwick Street and Route 5. There is an in-town hotel, a waterfront park, and a winery. Historic sites are Tudor Hall which houses the St. Mary’s County Historical Society, and the Old Jail Museum. Leonardtown holds numerous weekend events including First Fridays.

First Fridays in Leonardtown

First Friday in Leonardtown is back on the first Friday's of the month from 5 p.m. - 8 p.m.!

Come enjoy dinner at one of the many local restaurants, enjoy a drink from Social Coffeehouse or Antoinette's Garden, explore Shepherd's Old Field Market, shop at one of the many local shops and art galleries, and enjoy a sweet treat from Heritage Chocolates!

Make sure to take a tour of the Old Jail Museum and to participate in the Drum Circle from 7 p.m. - 8 p.m.!

Click below for future dates.

First Fridays Event Page


With a variety of shops, galleries & more, this small town has what you are looking for.


From fine cuisine to pub grub, your dining options in Leonardtown are many.


Leonardtown's activities, including a winery, a wharf, and historical sites, means you will always find something to do.


Download the Map and Quick Guide for a map and overview of Leonardtown and St. Mary's County.

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