Leonardtown is the county seat of St. Mary’s County, Maryland, on the western shore of the Chesapeake. The town square holds the shops, galleries and restaurants, and the wharf sits down the hill on Breton Bay with a boardwalk, a playground, boat slips and an ADA kayak launch. The county around it is still working farmland, with Old Order Mennonite and Amish farms, a produce auction at Loveville, and empty tobacco barns standing in fields where nobody grows tobacco anymore. I did not go back this spring as a traveler. I went home to be with my dad at the end of his life.
Key takeaways
- Leonardtown is small, walkable and free to wander. The square and the wharf are the two things to see, a short walk apart down Washington Street.
- First Friday runs 5:00 to 8:00 p.m. every month, with shops and galleries open late.
- The wharf is a public park on Breton Bay: boardwalk, benches, playground, boat slips, floating dock and an accessible kayak launch.
- Social, the coffee shop, is in the old Duke building on the corner of Fenwick and Washington.
- The county is genuinely agricultural. The Loveville Produce Auction runs most Mondays, Wednesdays and Fridays, and horse and buggy traffic on the county roads is normal.
- Tobacco is gone as a crop here. The barns are still standing.
What is in this post
- Where this is
- Why was I there?
- What is Leonardtown actually like?
- What is at the wharf?
- Is St. Mary’s County still farm country?
- What the farm looks like in spring
- What a few weeks at home is actually made of
- Common questions
Where this is
St. Mary’s County sits at the bottom of Maryland’s western shore, where the Potomac meets the Chesapeake. Leonardtown is its county seat and has been since the early eighteenth century, when it was described as “a most convenient place.” The courthouse, the hospital and the county government are all still there. So is the Religious Freedom National Scenic Byway, and two small history museums: Tudor Hall, which houses the St. Mary’s County Historical Society, and the Old Jail Museum on the square.
Why was I there?
I came home to St. Mary’s County in March 2026 to be with my dad at the end of his life. I wanted to spend time with him and help take care of him.
After he died, I stayed for a while. I visited extended family, helped my mom with the transition, and spent time with my best friend.
What is Leonardtown actually like?
Small, and the good kind of small. The shops, galleries and restaurants sit around the town square and along Fenwick Street and Route 5. There are used book stores and craft spaces and outdoor tables. On the first Friday of every month the town runs First Friday, 5:00 to 8:00 p.m., and the shops, restaurants and galleries stay open with exhibits and late hours.
There is a winery in town and a paddling trail on Breton Bay. That is close to the whole list, and the list being short is the point. You are not going to Leonardtown to get through an itinerary.
I don’t drink coffee, but I still ended up at Social, the coffee shop downtown. It is in the old Duke building on the corner of Fenwick and Washington Streets, a 1920s brick building that used to be Duke’s Fountain-Bar-Restaurant. My brother and I, or the three of us with my mom, also went into town to eat a few times.
What is at the wharf?
The wharf is down the hill from the square, along Washington Street, on Breton Bay. It is a public park: a boardwalk, park benches, a playground, boat slips, a floating dock and an ADA-compliant kayak launch. Canoe and kayak rentals run from there, along with sunset cruises, paddleboard classes and, improbably, seaplane rides.
It is also the town’s event space, which is why half the photographs you will find of Leonardtown online are somebody’s wedding.
Is St. Mary’s County still farm country?
Yes, and more than most people expect from a county that also hosts a naval air station.
There are established Amish and Mennonite communities here, and horse and buggy traffic on the county roads is ordinary, not a curiosity. Loveville has an Old Order Mennonite community and runs a wholesale produce auction most Mondays at 11:00 a.m. and most Wednesdays and Fridays at 9:00 a.m., with a small lot auction starting half an hour after the main one. North of there, the Farmers Market and Auction at 30030 Three Notch Road in Charlotte Hall is a seven acre market open Wednesdays, Saturdays and Sundays year round, with Amish and Mennonite produce and baked goods.
And then there are the tobacco barns. Tobacco was the crop here for centuries and it is not grown anymore. The barns are still standing in the fields, empty, and once you know what you are looking at you cannot stop seeing them.
What the farm looks like in spring
The farm was a place that meant a lot to my dad. His donkeys are there, along with the sheep, the alpaca and the cats, and I went to visit them while I was home.
April there is pretty. Flowers blooming, green grass, and mornings that are still cold.
We spread some of his ashes on the farm.
What a few weeks at home is actually made of
Not big moments. In March there was still snow on the field, and by the middle of April the same field was green.
Most of it was the ordinary business of being somewhere: meals at the kitchen table, the drive into town, the animals to check on, a cat who had opinions about which quilt was hers.
Common questions
Where is Leonardtown, Maryland?
Leonardtown is the county seat of St. Mary's County, on Maryland's western shore where the Potomac River meets the Chesapeake Bay.
Is there anything to do in Leonardtown for a day?
The town square and Leonardtown Wharf on Breton Bay are the two anchors, along with Tudor Hall, home of the St. Mary's County Historical Society, and the Old Jail Museum. It fills an unhurried half day, or longer if you paddle Breton Bay.
When is First Friday in Leonardtown?
The first Friday of every month, from 5:00 to 8:00 p.m., when shops, galleries and restaurants around the square stay open late.
Is there a coffee shop in Leonardtown?
Yes. Social sits in the historic Duke building at 41655 Fenwick Street, on the corner of Fenwick and Washington, a 1920s brick building that used to be Duke's Fountain-Bar-Restaurant. It roasts its own coffee.
Can you launch a kayak at Leonardtown Wharf?
Yes. Leonardtown Wharf has an ADA-compliant kayak launch, plus canoe and kayak rentals, boat slips and a floating dock.
Where can you buy Amish and Mennonite produce in St. Mary's County?
At the north county farmers markets, including the seven acre Farmers Market and Auction at 30030 Three Notch Road in Charlotte Hall, open Wednesday, Saturday and Sunday year round. The Loveville Produce Auction is a wholesale auction held most Mondays, Wednesdays and Fridays.
Is tobacco still grown in southern Maryland?
No. Tobacco is no longer grown as a crop in the area, though empty tobacco barns still stand in fields across St. Mary's County.
Planning a trip and want someone else to do the legwork? My Travel Concierge Service helps you build a trip that actually fits how you like to travel. For more practical guides and insider tips, join the newsletter.
More from that spring in Maryland: North Beach, Maryland in the Off Season, The St Mary’s Lake Loop Trail and Ocean City, Maryland With a Dog in the Off Season
0 Comments