Going Home to St. Mary’s County: Leonardtown, a Family Farm, and a Spring I Did Not Plan For

Destined for Adventure blog cover card: Going Home to St. Mary's County.

Written by Hannah

Uncategorized

September 20, 2026

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.

A flock of sheep coming out of an old barn into a green field at golden hour.
April on the farm. The flock comes out of the barn on its own schedule, not yours.
A man sitting at a kitchen table with a plate of food in front of him.
My dad, at the table where most of that month happened.
Four family members standing together in a wood panelled living room.
March 6, the first week I was home.
The brick Duke's building on a Leonardtown corner, its old sign reading Duke's Coffee Restaurant Bar with Social below it.
The old Duke's building on the corner of Fenwick and Washington. It is Social now, with its own roastery.
Sunrise over Breton Bay at Leonardtown Wharf, with boats moored along the dock.
The wharf at 6:22 in the morning, which is the only time it belongs to whoever showed up.
A dirt farm lane running past a blue metal barn and a round hay bale.
The lane in, which is most of what I remember about being there.
Three donkeys crowding around a woman on a dirt lane in bare early spring woods.
My dad's donkeys. They come to meet the car, and then they do not leave.
A donkey pushing its nose up to a car window from outside.
This is what happens if you roll the window down.
An alpaca standing in a wooden stall with a feed bowl at its feet.
The alpaca, who did not want to discuss it.
An old barn across a green field, with sheep gathered in front of it.
The same barn from the field side, mid April.

We spread some of his ashes on the farm.

A pink lady's slipper orchid blooming in brown leaf litter.
Pink lady's slipper, wild in the leaves. They take years to flower and they do not transplant.

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.

A snow covered field at the edge of bare woods.
Mid March, and it was still doing this.

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.

A tabby cat stretched out asleep on a patchwork quilt.
The other job at the house.

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.

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

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