Chestertown is full of old bricks. You walk down High Street and every second house looks like it has a story that involves a quill pen and a tricorn hat. But if you head south toward the edge of town, right near Wilmer Park, you run into a place called Stepne Manor Chestertown MD.
It isn't just "another old house."
Most locals call it the "White House Farm" or just "Stepne." If you're looking for it on a map, you'll find it at 406 South Cross Street. It sits there, kind of grand but also surprisingly tucked away, overlooking the Chester River. Honestly, if these walls could talk, they wouldn't just tell you about weddings and parties; they’d tell you about the very birth of the town itself.
The House That Pre-Dates the Town
Here’s the thing that trips people up: Stepne Manor (often spelled Stepney in the old records) was there before Chestertown was even a glimmer in a surveyor’s eye.
The original land grant goes back to Dr. Richard Tilghman in the mid-1600s, but the real story starts with Simon Wilmer. He’s the guy who basically invented Chestertown. In 1706, the colonial government decided they needed a port of entry for the Eastern Shore. Wilmer was the one who laid out the grid of streets and sold the lots.
Where was he living? Right there at Stepne.
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The back wing of the house—the part people usually ignore because it’s not as "fancy" as the front—dates back to roughly 1690. Some architectural historians at the Maryland Historical Trust even think parts of the cellar might be from 1659. That makes it one of the oldest structures in Kent County.
Architectural Weirdness and 19th-Century Glow-Ups
If you look at Stepne Manor today, you aren't looking at a single building. It’s a bit of a Frankenstein’s monster, but in a very elegant, Maryland-brick sort of way.
The house is an L-plan. You’ve got the old 17th-century brick section, and then you’ve got the massive "new" addition from the 1820s. This front part is a three-story brick structure with a gambrel roof and those classic shed dormers that look like they’re peeking out at the river.
It’s got that signature Flemish bond brickwork—where the "headers" (the short ends of the bricks) are glazed to create a shimmering pattern. You don't see that much anymore because it was incredibly labor-intensive.
- The Porch: There’s a huge, pedimented porch with Doric pilasters. It’s the kind of place where you want to sit with a glass of tea and pretend it's 1850.
- The Floors: Inside, you’ve got wide-plank oak floors that have been polished until they glow.
- The Layout: It’s a central hall plan, which was the "open concept" of the 19th century. It allowed for a cross-breeze, which, before air conditioning, was the difference between life and a very sweaty death in a Maryland summer.
Who Owns Stepne Manor Now?
For a long time, the property was in the hands of the Lusby family. They used the land to train horses, which explains why the grounds feel so much more expansive than a typical town lot.
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Fast forward to the late 1980s, and KRM Development Corporation bought it. Today, it’s managed under the Brittland Estates umbrella. This is why you see it all over Instagram as a wedding venue. It’s part of a trio of properties they run, including the Bank and Brittland Manor.
While Washington College owns some of the surrounding farmland, the manor house itself is private property used for short-term rentals and events. In 2026, it’s still one of the most sought-after spots for people who want that "rural sophistication" vibe without actually being in the middle of nowhere.
What It’s Like to Actually Stay There
If you’re thinking about booking it, don't expect a sterile hotel experience. It’s a house. A big, old, slightly creaky house.
It sleeps about 15 people across 5 bedrooms. The renovation in the mid-2000s did a lot to modernize it—they added central air and updated the kitchen—but they kept the period hardware and the "character."
The real draw isn't the bedrooms, though. It’s the fact that you can walk to downtown Chestertown in five minutes. You can hit the Farmer’s Market on Saturday morning, grab a coffee at Play It Again Sam, and be back on the Stepne porch by 10:00 AM.
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It’s quiet. You get the view of the horses in the fields nearby, but you’re close enough to hear the bells from the town. It’s a weird, perfect middle ground.
Things You Might Not Know About Stepne Manor Chestertown MD
There is a painting at Washington College that shows the farm in the 1790s. In the painting, Simon Wilmer is riding his horse across the plantation. If you look closely at the background, you can see the early buildings of the college and the harbor. It’s proof that Stepne has always been the "anchor" for this side of town.
Also, it’s technically "National Register Eligible." Even though it’s a private venue, the Maryland Historical Trust keeps a very close eye on it (under inventory number K-85). They recognize it as a "White House Farm," a name that dates back to when the house was likely painted or whitewashed to stand out against the green fields.
Actionable Tips for Visiting or Booking
If you're planning a trip to see Stepne Manor Chestertown MD, or if you're lucky enough to be attending an event there, here is how to handle it like a pro:
- Check the Sound Curfew: If you're hosting an event, remember that Chestertown is a quiet town. Music has to wrap up by 10:00 PM. Don't be that person who gets the cops called on a historic estate.
- Walk the Lane: Don't just stay on the lawn. Take the walk down to Wilmer Park at sunset. This used to be the manor’s original waterfront, and the view of the Chester River from there is the best in the county.
- Parking is Tight: Even though there's a "circle," if you have a big group, use the self-parking area. Don't block the brick pathways; those bricks are old and they don't like heavy SUVs.
- Explore the Outbuildings: There’s an old corn crib and some equipment sheds to the west. They aren't open to the public, but they give you a sense of just how much of a working farm this used to be.
- Visit in the "Shoulder" Season: May and October are the peak for a reason. If you want to see the architecture without the crowds, try a walk-by in early November when the leaves are down and you can see the brickwork clearly from Cross Street.
Stepne isn't just a place to sleep. It’s a 300-year-old witness to everything that’s happened in Kent County. Whether you're there for a wedding or just walking past on your way to the river, it’s worth taking a second to appreciate the fact that it’s still standing. Most houses from 1690 are long gone, but Stepne just keeps evolving.