The murky history of Tippity Wichity, a private island for sale off the Chesapeake

Published on: November 03, 2022 6:00 AM EDT|Updated on: November 03, 2022 9:54 AM EDT

An aerial view of the island that shows the wooded areas and the dock.
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A five-acre island in the St. Mary’s River, known as Tippity Wichity, might be your best chance at owning a private island near the Chesapeake Bay. It’s currently listed for sale with Monument Sotheby’s — for a casual $2.1 million.

If you were to purchase the island, you’d get just less than five acres of private land, complete with a three-bedroom home, a heated, in-ground pool, a private forest and more. The island has a dock and the property includes a permanent easement on the mainland with a dock and parking pad, so access to the island is guaranteed.

“It’s very private, it’s like your own personal kingdom,” said Dave DeSantis, a realtor working on the sale. “There’s a lot of charm and intrigue associated with that.”

The current owners, John and Gail Harmon, are getting older and thought it was the right time to sell, since it can be challenging for them to get in and out of the boat that takes them to and from the island, Gail Harmon said.

The Harmons never lived on the island full time, but Gail Harmon said she has many fond memories of having friends over for parties and swimming in the pool together.

”A favorite [memory] could be sitting on the front lawn, looking down the river. We can sit there with another couple and have cocktails and look down the river. That’s just special,” she said.

What may make the island stand out even more, though, is its checkered past. There’s a history to Tippity Wichity Island, though the exact story depends on who you’re asking.

According to the listing, arrowheads and pottery shards have been found on the island, indicating it could have once been a home to Indigenous Americans. Old county records indicate that a Captain Henry Howgate bought the island after the Civil War in 1878 — though it’s unclear whether he fought for the Union or the Confederacy.

Howgate built a distillery and “house of ill-repute” on the island, according to the listing, apparently taking advantage of its waterfront location after other similar establishments in Alexandria, Virginia, were forced to close.

Gail Harmon said she’s “pretty sure” about two stories related to the island’s history. One, there was certainly a large, Victorian home that burned down — someone who lived nearby used to tell her and her husband stories about exploring the abandoned mansion as a child. And she’s certain there was some sort of distillery operation.

“We met the guy from one of the stories, who had been [on the island] as a kid, when his father was a bootlegger,” she said. “If the feds were coming up the river, and you could see them a long way off, they would just roll the barrels [of alcohol] off the back of the river and say, ‘Oh, we’re just having a picnic.’”

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The island was purchased by a man named Earnest Dickey in the 1950s, and he, too, made history: The house he built was the first in the county to be wired with an electric heat pump.

And what about the name of the island? According to Chesapeake Bay Magazine, local lore says the name is a shortened version of ”Tippling and Witchery Island,” a potential reference to being intoxicated — and to that ”house of ill-repute.”

Then in 1978, the Harmons purchased the island after seeing the house for sale in a classified ad in the back of Washingtonian magazine. Over the years, they upgraded the home to fit their needs.

Since then, the couple has spent time playing games by the fire with their family, quietly walking through the woods and listening to the great blue herons who share the island.

”It’s been quite remarkable,” said Gail Harmon. ”It’s like having 100 acres, except we probably have four.”