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Why is it that one building manages to survive for centuries while all the others built at about the same time fall victim to the ravages of time? One of the experts who has spent some time with what is believed to be the oldest house in Eastern Shore Road TripsChincoteague—it’s still standing after 200-plus years—chalked its survival up to a magical mix of being “well built, unusual, and lucky.”

Luck definitely has a starring role in this story. On a brisk, windy morning in April of 2015, I drove across the causeway into Chincoteague and headed north on Main Street, away from downtown and out past the high school. A couple of winding bends in the road later, I pulled over and parked near the historical marker that stands next to an itty bitty little house measuring just 17 feet by 16 feet.

Native Islander Cindy Faith-Oehm was waiting for me there. The owner of Island Arts, a gallery located across from Mr. Whippy on Maddox Boulevard, Cindy is one of the handful of local folks who serve as volunteer docents at the Captain Timothy Hill House, opening the place up for tours once a week during the warm months and on other occasions in response to special requests like mine.

Experts say the Hill House was built around the year 1800. To put things in perspective, that was the year that Beethoven’s 1st Symphony in C was performed for the first time. It was also the year that Washington, DC became our nation’s capital—John Adams became the first president to move into the White House that November 1st.

Timothy Hill House Before RenovationBut when Cindy starts into the story of the Hill House, she begins not way back then, but in the 1980s. At that time, the house stood in another part of town that was being eyed for the residential development now known as Deep Hole. The house was already in pretty sad shape by that point, having been vacant for years.

One of the real estate agents involved in that deal seems to have had a soft spot for dilapidated old houses. Before demolition got under way for Deep Hole, he arranged to have the Hill House moved on his own dime to a property on North Main Street, where it stood for another quarter of a century. The photo at left up top here and the one just above were taken towards the end of that stretch.

Cindy told me that she used to lead bus tours of tourists through town during those years. Whenever she went by this site, she would always point to the sad old house and say, “If any of you have an extra million dollars or so, I have a project for you.”

The next bit of luck arrived in 2009, when a pair of Broadway actors, Louisa Flaningam and Paul Brzozowski, showed up on the scene. Inspired by Louisa’s fond memories of childhood trips to Chincoteague and her enduring affection for the Island’s famous ponies, the New Jersey couple had purchased a second home on the Island. When they decided to add a storage shed for bicycles and tools to their new property, they thought about the dilapidated old building that they had driven past so many times.

Timothy Hill House Ship CarvingWhen Flaningam and Brzozowski bought the Hill House, they knew almost nothing about its back story. Luck intervened again on the day they had a contractor come out to see the place. During the inspection a piece of exterior clapboard fell off, revealing not just the original wooden exterior of the building, but also the intriguing image of a ship that had been carved roughly with some sort of knife.

Their curiosity piqued, Brzozowski and Flaningam asked a friend for advice. That friend, Carl Lounsbury, just so happens to be an architectural historian with the Colonial Williamsburg Foundation. Despite a caved-in roof and an abundance of rotting wood, Lounsbury and the team of experts he had in tow immediately recognized the structure as a rare find—a two-century-old “plank home” with a wooden chimney.

“The way that I heard the story, the moment they all saw this house, they looked the way children do when they’re opening up gifts on Christmas morning,” Cindy told me.

Louisa Flaningam inside the Hill HouseHow rare is the Hill House? It is believed to be one of just two structures with a wooden chimney still standing in the state of Virginia. Cindy explained to me how the chimney was constructed with a makeshift latch and pulley system so that it could be detached quickly and then pulled away in the event of a fire, keeping the main part of the home safe.

There is a story behind the “plank” style of building as well. It’s a type of construction first brought to these shores by Scandinavian immigrants to the Delaware Bay area. It spread up and down the coast in part because it was so affordable—farming families and middle-class craftsmen and merchants were able to cut everything they needed to build a house on their own, bypassing the need for  expensive help from experts.

In an interview with Preservation Magazine in 2010, Lounsbury counted the Hill House among only a “very few” plank homes still standing in the region.

Louisa Flaningam inside the Hill HouseCindy shared lots of interesting tidbits during my visit. Once restoration work began, workers uncovered 21 generations of paint colors on the front door—most all those layers remain visible on the inside part of the door (picture below). The original color used in much of the interior of the house was probably the rich blue you can see in some spots on the mantle in this photo. That mantle is original to the house, by the way.

There is a wide open second-floor loft space in The Hill House. At different times over the centuries the building housed families with lots of kids—seven in one case, nine in another. Let me pause here and repeat myself: The footprint of The Hill House is just 16 feet by 17 feet.

The children presumably slept en masse upstairs in this loft, and Cindy laughs about how workers found evidence of a latch that would have locked the door to the loft from the outside, at the top of the stairway, presumably providing a few much-needed moments of parental privacy after the children’s bedtime each night.

Timothy Hill House Layers of Paint on DoorRemember that rough carving of a ship that appeared when some clapboard fell? That was just the beginning of that turn in the story of the Hill House, because it turns out there are 38 additional carvings, all of ships, in the exterior wood. If you can find all 39 of them on your visit to the house, well, then I will have to concede that you are a better treasure hunter than I am.

No one has solved the mystery of the carvings so far. Cindy’s theory is that a child did them. She points out that the house has been elevated so that it stands today 18 or so inches above where it would have back in the day. Once you consider that adjustment, she says, it becomes clear that many of the carvings are at the right height to be the work of a 12-or-so-year-old boy.

Another fun fact: The window frames are original to the house. As for the windows themselves, they came from a house in nearby Girdletree, just across the Maryland line, and that house was built about the same time as the Hill House.

And then there were the stories Cindy had to tell of the Hill family. Legend has it that Timothy Hill came to Chincoteague in dramatic fashion, as a teenaged shipwreck survivor, and then stayed for the rest of his life. In census records, he identified himself as a sailor from New York. He worked for a shipping company for a while, then started up his own firm, delivering seafood and other goods to Philadelphia and other cities.

Hill’s first appearance in official records came when he bought real estate in April 1822. He seems to have been quite active in real-estate transactions in the years that followed–at the time of this writing, Louisa was trying to sort through all of these details.

Hill’s marriage to local girl Rebecca Russell came in May 1822. Timothy and Rebecca raised six children. One of them, Timothy Jr., went into the oyster business and became one of wealthiest men on the Island in the late 1800s.

Incredibly, the home remained with the Hill family clear up until 1954. A gentlemen named Jack Hill was the last descendant known to have actually lived in the house. There are still a good number of Hill descendants living in town and in the area—some of them come out to the Hill House now and again for visits and to check in on the progress of restoration work.

One more Hill House claim to fame—or in this case, infamy: It was the site of a grisly and much-publicized crime, the June 1885 murder of 13-year-old Jennie Hill. Jennie and her mother, Zipporah (who survived the attack), were shot by a 22-year-old farmhand who was hopelessly smitten with young Jennie but unable to win her parents’ approval for a wedding.

The killer, Tom Freeman, blew his own head off afterwards. Freeman left a badly spelled note that said, in part, “good by to all and to everybody this is my request to be Bury long a side of hear.” (After finding my way to some cool old newspaper material about that crime a few months after posting this, I worked up this item that goes into more detail about the crime.)

The restoration remains a work in progress. Cindy told me that the focus nowadays is on restoring the old wooden chimney, and I have since read in the newspapers that work is under way on that project as of the fall of 2016. Lots of other tasks remain on the to-do list for future years as well. In the meantime, I am happy to report that the Hill House is the only structure in Chincoteague listed on both the Virginia Landmarks Register and the National Register of Historic Places.

So who knows? With all these generous people pitching in, maybe the Hill House’s run of good luck will continue long enough for it to survive for another couple of centuries.

— Written by Jim Duffy

• The Hill House is located at 5122 Main Street in Chincoteague. Its website has directions and lots of photos, as well as information about tours. (The exterior of the house is always open for visits. As of this writing, the interior is open on Fridays from 1-3pm in the summer months or by appointment.)

• Brzozowski and Flaningam have financed a good amount of the restoration work themselves. They have also received lots of in-kind donations, including quite a bit of labor by generous local craftsmen. They also accept monetary donations to History Keepers, LLC, the private company they have formed to manage the project and its finances. Here is information on how you can help.

Joshua Chandler Grave in Chincoteague

• Nearby: If you continue north on Main Street for a bit and reach the roundabout-shaped dead end that locals call “The Turntable” you will find the grave of Captain Joshua L. Chandler, who died in 1877. The inscription on his stone is somewhat famous. It reads, “Farewell wife and children dear/I am not dead but sleeping here/As I am some day you will be/Prepare for death and follow me.” The fact that neither his wife nor children are buried here with Captain Joshua is another story that I’ll have to look into someday.

• There is lots and lots of interesting stuff to see and do in Chincoteague–here is the Chamber website, as well as on the broader Eastern Shore of Virginia.

• The two photos of the pre-restoration house come from the Hill House website and appear here courtesy of Brzozowski, Flaningam, and History Keepers, LLC. The same goes for the photo of Louisa Flaningam seated in a lawn chair with one of the notebooks she uses to keep track on the renovation. The rest of the photos are by Jim Duffy.

• If you are interested in Chincoteague stories, there are a few other things on this site that you might find of interest. Here is a daytrip to Assateague Island. Here is “The True Tale of Misty, Stormy, and maybe the worst nor’easter of them all.” Here, on the occasion of its 90th birthday in 2015, is a history of the famous midsummer pony swim. And here is a piece about a one-of-a-kind Chincoteague character from back in the day, the decoy carver Miles Hancock.

• Last but not least: Thanks for reading!




  • Thank-You for the article. I am so happy to hear the story that goes with this house. I was around 10 years old; when I first visited Chincoteague. I always dreamed of sleeping and living in a Chincoteague house. I was able to rent a House on Main St. , It was remolded, but I love it. I wish Chincoteague could be restored to the fishing village it was years ago; progress is not always a good thing. Chincoteague is a fantastic town as are the citizens of Chincoteague .

  • Jan MacKinnon says:

    Fascinating and appreciated story,! but please check your spelling of “Chincoteague” in the title :)

  • Ken Bowden says:

    Thank you for publishing this wonderful bit of history about the Hill House. I am a native of Chincoteague Island, born in 1950 to a long line of Bowdens who were among the original settlers on the island. So much has changed about “home” since I was a boy, but I am very pleased to see such great interests from visitors from other areas who take an interest in preserving the history of Chincoteague Island.

  • Aaron Money says:

    This is a great article. My mother was a Hill and was raised on the island. We still have family there even though we now live in Indiana. Mom recently donated an antique bed to be displayed in the house. I cannot wait to visit there again.

  • Adrian says:

    My grandmother grew up in that house and my father spent the first 2 months of his life there. I have a pic of the original structure. Im told told the existing structure was the kitchen at that point in time at least. You can see in the photo that there was an addition.

  • John curtis sn says:

    John curtis I grew up just off the island in the town of atlantic the island has changed alot but still go back every year for vacation it will always be home to me

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