It seems that there’s a piece of unexpected history everywhere you look in Massachusetts The Jailhouse Tavern in Orleans was once used as the town jail. Today, it’s a local landmark that serves some truly delicious fare. Read on to learn more about how you can dine in a real former jail.

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The Jailhouse Tavern has a colorful history soaked in rum and saltwater. In the 1920s and 1930s, bootleggers smuggled liquor along the coast of Orleans. They would hide their goods in coves and inlets along the water before loading it into trucks to be driven off the Cape under the cover of night. As you might expect, this illegal activity led to quite a few arrests.

Town constable Henry Perry offered his front bedroom as a lockup to contain the bootleggers until they could be taken up Cape to more secure accommodations. Perry would lock the prisoners into his spare bedroom, which had been outfitted with bars and padlocks, and then retire to his own bedroom for a good night’s rest. In the morning, the prisoners would be transported to Boston or to other local jailhouses.
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Today, the Jailhouse Tavern celebrates this unique part of Cape Cod history with great food and drink. The restaurant still features polished jail cell bars, a giant bar gate entrance, three different dining areas and a handsome oak bar. There’s also a lovely patio with umbrellas and comfortable seating for when the weather cooperates.

The menu here is an eclectic mix of seafood classics, traditional New England fare and unexpected twists. Try the delicious Lobster Corn Fritters with sriracha aioli or the White Truffle Lobster Mac and Cheese for starters. For you main, choose from a selection of mouthwatering dishes like the Tavern Cod with whipped potatoes, the Gourmet Veggie Burger or the classic Fish and Chips with coleslaw.
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You can find the Jailhouse Tavern at 28 West Road, Orleans, Mass. They’re open Wednesday through Sunday, 11:30 a.m. to 9 p.m. Visit their website here for more information and current menus.

If you’re looking for an even more extreme dining experience, check out this restaurant located in an actual working Massachusetts prison and run by prisoners.

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