Guide
Leonardtown, MD: beer, wine and things to do
Leonardtown is the county seat of St. Mary’s County in Southern Maryland, and it is small enough to cover in a day. The town counted 4,563 residents in the 2020 Census. For a beer drinker the short version is one taproom downtown, a winery in a nearby park, and a calendar built around First Fridays.
What is Leonardtown known for?
Leonardtown is known as the St. Mary’s County seat, a historic downtown around a magnolia-lined square, a waterfront on Breton Bay, a state-designated arts district and the Moll Dyer legend. The town says it is the only incorporated municipality in the county with its own elected mayor and Town Council.
The records are old. County court met at the house of John Hammond by 1654, and an official town with a courthouse was set up in 1708, according to the town’s own history. It was renamed for Benedict Leonard Calvert. The state gave the Leonardtown Arts & Entertainment District its designation in 2013, and the Leonardtown Business Association now runs much of the event calendar.
Where is Leonardtown in Maryland?
Leonardtown is the county seat of St. Mary’s County, in Southern Maryland, about 16 miles north of the St. Mary’s College of Maryland campus. The college puts its campus 75 miles southeast of Washington, D.C. and 97 miles south of Baltimore, so Leonardtown is a little closer to both. Plan on a drive, not a train.
Is Leonardtown walkable?
Yes, downtown is. The town’s own wedding page puts it plainly, The description holds for the core:
“Once you arrive, you don’t need to drive, you simply walk everywhere.”
Town of Leonardtown, Leonardtown Wharf page, 2026.
That covers Leonardtown Square, the Old Jail Museum and the streets around them. Leonardtown Wharf is described as just down the hill from the Square. The Port of Leonardtown Park is a different matter, covered next.
The mental map: Square, Wharf, then the park
Hold three places in your head, because the names get mixed up. Leonardtown Square is the grassy town square with the War Memorial monuments, the Circuit Courthouse lawn and the Old Jail, a stone building from 1858 that served until 1942 and is now a museum. Historic Downtown Leonardtown, with its shops and restaurants, wraps around it. Shepherd’s Old Field Market and Fenwick Street are on the Leonardtown Business Association’s list of places to see.
Downhill is Leonardtown Wharf, a waterfront park on Breton Bay with a brick Compass Rose and a big lawn. It is a park, not a bar and not a winery.
Port of Leonardtown Park is a separate place. It sits beside McIntosh Run on Newtowne Neck Road, and the Port of Leonardtown Winery is on the same property at 23190 Newtowne Neck Rd. So the park and the winery share an address, and neither is the Wharf. The town publishes a Winery, Wharf and Water Trail brochure and a downtown parking map, and The town does not publish a walking distance from the Square to the park, so treat the park as a drive unless its Winery, Wharf and Water Trail brochure says otherwise.
Beer and wine in Leonardtown
Everyday Saint Brewhouse
Everyday Saint Brewhouse is a nano-brewery at 22760 Washington St. Its taproom opened on December 6, 2025, per the Maryland Beer Journal, and Mid-Atlantic Brew News reported the same date in its December 2025/January 2026 issue. The room seats only 24, there is a lot of outdoor seating around two fire pits, and it takes cards only. The brewery makes 7 to 10 rotating styles. The brewery’s own site lists Thursday 3 to 9 and Friday and Saturday 12 to 10. The beer came first, though: it had been brewed in the basement of the building, known as the Duke House, for about two years. Hours change, so check the brewery’s site before you walk over.
Port of Leonardtown Winery
The winery’s tasting room runs 12 to 6 every day, with music starting at 2 PM, and the site describes wines by the glass, seasonal wine slushies. Check its own site for the event calendar and current hours.
Other places in town
Olde Town Pub, Brudergarten, The Rex and Wine and Design appear in other Leonardtown listings but are not covered here; check their own pages for hours. The Old Jail Museum doubles as the Leonardtown Visitor Center, so it is the place to pick up the current brochure. For a market, the 2026 calendar lists a First Saturday Market Series on November 7 and December 5; confirm the location on the town calendar. The 2026 calendar does not list a weekly farmers market on the Square.
What is First Friday in Leonardtown?
Leonardtown First Fridays happen on the first Friday of every month, year-round, when galleries, restaurants, cafes and shops open up with specials or local art. They are sponsored by the Leonardtown Business Association with the Town of Leonardtown. From May through October they stretch into whole weekends.
The official 2026 list has 12 entries. Octoberfest ran October 2 to 4, and the Scarecrow Stroll runs October 3 to 31, 2026. Still ahead are Passport to the Holidays on November 6 and Gingerbread Lane on December 4. Check the First Fridays page for updates.
What is going on in Maryland this coming weekend?
Events move faster than a guide, so use the calendars. For Leonardtown, use the town and Business Association calendars and the First Fridays page above. For the rest of the state, Visit Maryland is the official hub, and our Maryland breweries guide has the regional picture for beer.
Is Leonardtown, MD a good place to live?
That depends on what you want, and one guide cannot answer it. The numbers I can source are modest: the 2020 Census counts 4,563 residents, up from 2,930 in 2010, with a median age of 38, per the Maryland State Data Center profile. For taxes, utilities and services, go to the Town of Leonardtown’s resident pages rather than a listicle.
Near Leonardtown, not in it
These are drives, and they are separate places with their own hours.
Historic St. Mary’s City
Historic St. Mary’s City is the site of Maryland’s first capital, roughly 16 miles from Leonardtown by the college’s measure, not a Leonardtown attraction. Its Visitor Center is at 18751 Hogaboom Lane, and the site lists Tuesday to Saturday, 10 a.m. to 4 p.m., until November. A new Visitor Center opens November 14, 2026. For beer, Angelika’s Kitchen runs The Farthings Pub, which advertises craft beer, fine wines and dry cider. The pub is open Thursday to Sunday, 11 a.m. to 7 p.m., and on Wednesdays the kitchen runs 11 to 3 with the pub closed. The site lists a 0.43 mile walk from Farthing’s to an exhibit.
The Farthings Fermenter is the new name for the brewery that grew out of Jubilee. Its owner said in late 2025 that its beer would go to the new Farthings Pub and select St. Mary’s County accounts.
Sotterley
Historic Sotterley in Hollywood ended its 2026 guided tour season on October 18. Tours, the Visitor Center and the exhibits are closed until May 2027, though the grounds, gardens and trails stay open with winterized restrooms.
St. Clement’s Island
The island is reachable only by boat. The county’s water taxi ($7 round trip as of June 2026) ended its 2026 season on October 13 and returns in March 2027. The museum building is being rebuilt, with reopening planned for Maryland Day week in March 2027. Call (301) 769-2222 before planning a trip.
Moll Dyer: the legend and the rock
The legend says Moll Dyer, believed to be a healer south of today’s Leonardtown, was accused of witchcraft in the winter of 1697 and found in February 1698 with a hand frozen to a rock. Treat that as legend. The location is a fact: the Moll Dyer Rock sits at Tudor Hall, home of the St. Mary’s County Historical Society. The St. Mary’s County Historical Society moved the boulder from the Old Jail to Tudor Hall in early 2021 and held an unveiling on February 26, 2021. It had sat by the Old Jail since 1972.
One Saturday: St. Mary’s City and Leonardtown
- 10:00 Historic St. Mary’s City grounds (open Tuesday to Saturday until November).
- 11:30 Lunch at The Farthings Pub, Thursday to Sunday only.
- 1:30 Drive north to Leonardtown and walk the Square, the Old Jail and Tudor Hall.
- 3:00 The winery, with music from 2 PM per the winery’s site, so check the day’s lineup and the tasting room open to 6.
- 6:15 Everyday Saint Brewhouse, open to 10 on Saturdays.
Swap in the Wharf for the winery if you prefer a bay view to a vineyard. Thursday works too; on a Friday, the First Friday crowd adds a good reason to stay late.
Where Jubilee fits in Leonardtown’s beer story
This site’s namesake also brewed here. Jubilee Farm Fermentations was a farm brewery on Pear Hill Rd in Leonardtown. Its first season ran July 2 to August 20, 2022, on Saturdays from 3 to 8 pm, with beer and young wine by the glass in a courtyard among the vines. Its beers included Moonlite, a dark beer, and Miami Sunrise, a fruity one, and it sold at Home Grown Farm Market and Greenbelt Farmers Market. In late 2025 its owner, Daniel Bedford, said the brewery would move to Historic St. Mary’s City in early 2026 as The Farthings Fermenter. This site is the archive of those Leonardtown years. See the about page for the story and the Southern Maryland breweries guide for the region.