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

1. Where this is
2. Why was I there?
3. What is Leonardtown actually like?
4. What is at the wharf?
5. Is St. Mary’s County still farm country?
6. How do you get to Leonardtown?
7. What else is worth seeing in St. Mary's County?
8. What should you eat here?
9. Where do you stay?
10. When should you go?
11. What does a day in Leonardtown look like?
12. What the farm looks like in spring
13. What a few weeks at home is actually made of
14. 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.

How do you get to Leonardtown?

Leonardtown is about 60 miles south of Washington DC, roughly an hour and a half on MD-5. You will want a car.

• From DC: MD-5 South (Branch Avenue), about 60 miles and 1.5 hours depending on traffic.
• From Baltimore: about 80 miles, I-97 South to MD-3, then MD-5, 1.5 to 2 hours.
• From BWI: about 85 miles, 1.5 to 2 hours.
• The scenic way in: MD-4 South over the Thomas Johnson Bridge at Solomons, then MD-235 through Lexington Park.
• Without a car: the MTA Commuter Bus 725 runs weekdays between downtown DC and Charlotte Hall ($6 one way) or California, Maryland ($8). The county’s St. Mary’s Transit System buses went fare free in July 2025.

What else is worth seeing in St. Mary’s County?

The county is where Maryland started, and most of the history is still standing.

• Historic St. Mary’s City: the site of Maryland’s first capital, founded in 1634 after the Ark and the Dove landed. It is an outdoor museum with a tobacco plantation, a Woodland Indian hamlet, a replica of the Maryland Dove and a reconstructed State House. In 2026 it was $15 for adults, open Tuesday to Saturday 10 a.m. to 4 p.m., March to November.
• Historic Sotterley: a tobacco plantation on the Patuxent River with a 1703 manor house and the only surviving original 1830s slave cabin. Guided tours are $12 for adults, or $5 for the grounds.
• Point Lookout State Park: the very tip of the western shore, where the Potomac meets the bay. There is an 1830 lighthouse and a 710 foot fishing pier, and it was the site of Camp Hoffman, a Civil War prison camp where nearly 4,000 of the Confederate soldiers held there died. Check the state park site for the day use fee and summer weekend reservations before you go.
• Leonardtown Wharf on the water: kayak and paddleboard rentals run from the wharf through the Patuxent Adventure Center.

What should you eat here?

Stuffed ham, which you will not find anywhere else. It is a corned ham cut open and packed with greens (kale, collards, mustard greens), celery, onion and red pepper, and it is the traditional Easter dish in St. Mary’s County. W. J. Dent & Sons in Tall Timbers sells it by the sandwich, $9, or by the pound, $15.99, as of late 2025. Chaptico Market and Murphy’s Town & Country Store in Avenue carry it too.

And oysters. At the end of March there was a whole tub of them. If you want them in public, the U.S. Oyster Festival at the county fairgrounds in Leonardtown is October 17 and 18, 2026, $15 a day for adults, and it hosts the National Oyster Shucking Championship.

Where do you stay?

The Inn at Leonardtown, if you want to walk to the square. It is a 40 room boutique hotel right off the town square, with breakfast and free parking. Lexington Park has the chain hotels near the naval air station, and Solomons has several bed and breakfasts. I stayed at home.

When should you go?

Fall is when the county puts on its best events. Spring is when the land is at its best.

• Fall 2026: the County Fair (September 24 to 27), Blessing of the Fleet (October 3), the U.S. Oyster Festival (October 17 and 18), and the Amish Quilt Auction (November 21).
• Spring: MarylandFest at Historic St. Mary’s City, a car show in downtown Leonardtown, and in mid April the pink lady’s slippers bloom wild in the woods. In mid March there was still snow on the fields. By mid April they were green.

What does a day in Leonardtown look like?

• Early: the wharf at sunrise. At 6:22 in the morning it belongs to whoever showed up.
• Mid morning: coffee at Social in the old Duke’s building, then a walk around the square, Tudor Hall and the Old Jail Museum.
• Lunch: a stuffed ham sandwich.
• Afternoon: Historic St. Mary’s City or Sotterley, or the long drive down to Point Lookout.
• First Friday: if your day lands on one, the square stays open late, 5 to 8 p.m.

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 his.

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.

How far is Leonardtown from Washington DC?

About 60 miles south on MD-5, roughly an hour and a half depending on traffic. Baltimore is about 80 miles and BWI about 85.

What is St. Mary's County stuffed ham?

A corned ham stuffed with greens such as kale, collards and mustard greens, plus celery, onion and red pepper. It is the traditional Easter dish in St. Mary's County. W. J. Dent & Sons in Tall Timbers sells sandwiches for $9 and ham for $15.99 a pound as of late 2025.

When is the U.S. Oyster Festival?

October 17 and 18, 2026, at the St. Mary's County Fairgrounds in Leonardtown. Day tickets are $15 for adults and it hosts the National Oyster Shucking Championship.

Is Historic St. Mary's City worth visiting?

It is the site of Maryland's first capital, founded in 1634, and now an outdoor museum. In 2026 adult admission was $15, open Tuesday to Saturday 10 a.m. to 4 p.m. from March to November.

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