About Us


During the 1920s and 1930s there were many tales of Prohibition era rum running on the Lower Cape. Bootleggers smuggled liquor into the small coves and inlets dotted along the bay by way of boat. Accomplices had fast trucks and would drive the goods off-Cape during the night.

Some tell stories about how these lawbreakers got caught in the early hours of the morning. Since Orleans has always been a town to extend a helping hand, it comes as no surprise that the town constable Henry Perry offered the front bedroom of his house on West Road as a Saturday night lockup. This property is now the Jailhouse Tavern where you sit today. Constable Perry was the only senior law enforcement officer in town at the time, and since there was no place on Saturday nights to transport those who would flout the law, he opened the doors of his home.

Perry, a friendly and trusting soul, simply locked his prisoners in a spare bedroom, secured with bars and locks, and retired to his room for a good night’s sleep. In the morning, the prisoners were taken up Cape to more secure surroundings. The stone walls of Constable Perry’s house frame the tavern room today.

In the early 1950s the Cape Codder published a series of stories about rum running on the Outer Cape, collecting reminiscences of Cape Codders barely twenty years after Prohibition ended:

“The leaders of the smuggling craft came from outside the Cape – but they had many Cape Cod recruits and many a tidy sum was netted by the local men who were familiar with the remote inlets, the best roads for getaway and were sensible enough to be guarded in their talk. The local men were relied upon to handle the drops – whiskey carefully packed into burlap sacks – and loaded them in fast trucks. A number were “all set” when the Prohibition era came to an end.

Much of the illegal liquor landed in North America on the French island of St. Pierre et Miquelon off Newfoundland, and was “delivered” on fairly large ships positioned on “Rum Row” three miles off the U.S. coast, and supplied the smaller boats venturing out there while trying to avoid the U.S. Coast Guard.”

Back in 1984 the vision was to create a restaurant where there was something for everybody and the Jailhouse Tavern, with its polished jail cell bars, three unique dining areas, an outdoor patio and handsome oak bar offers exactly that. Combine all this with an eclectic menu of fresh seafood, traditional New England fare and a great selection of Libations.

Thanks for joining us – Cheers!