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.

View Photos of this Area

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!

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!

Click on the link below for monthly First Friday specials, activities, and future dates!

First Fridays Event Page

Historic Leonardtown Itinerary

Looking for a great place to escape for the weekend? Historic Leonardtown, in the heart of Southern Maryland, is a short drive from DC, Baltimore, and Annapolis and has so many great things to do, see, and taste. Our free concierge planner will help you set up the perfect weekend getaway close to home - any time of year! We will help you plan the perfect trip, make sure you get VIP treatment while you are here, and give you complimentary welcome gift basket.

Itinerary 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.

Download Page 1 | Download Page 2