The Jailhouse Tavern in Orleans, MA

One of the best aspects of buying a home on Cape Cod is its eclectic dining scene, as you can visit a Brazilian steakhouse one day before heading to a seafood restaurant the next. There are plenty of five-star foodie experiences on the Cape, but you can always check out a home-style diner, too.

The late-night scene is equally as diverse, as you can spend some time at a dive bar, enjoy some drinks at an upscale wine bar, or visit Cape Cod's breweries.

Orleans has a unique venue called the Jailhouse Tavern that's full of stories and mystique. This restaurant and bar sits in a historic building that once acted as a temporary holding cell for criminals during the Prohibition period and features eye-catching décor from that era that is sure to get your attention.

Here's a look at what you can expect when visiting the Jailhouse Tavern in Orleans, Massachusetts. 

The Tavern's History

The story of the Jailhouse Tavern begins in the 1920s when rumrunners would smuggle liquor onto Cape Cod during the Prohibition era.

In those days, alcohol would often travel from Canada, Europe, or the Caribbean and arrive on Saint Pierre and Miquelon, a sparsely populated French island off the coast of Newfoundland. From there, cargo ships would transfer the liquor to a rum row, an area off the shore of a U.S. port where the Coast Guard has no authority. 

Ships would anchor in rum rows, three miles off the coast before April 21, 1924, and 12 miles afterward, and wait for smaller rumrunner boats to unload the liquor and take it ashore.

The smaller boats would try to evade the Coast Guard, reaching the ports of Cape Cod and transferring the liquor onto trucks. It would then be distributed all over the Cape.

Rumrunners would often operate in the middle of the night, making catching them a challenge. However, one issue on the Cape was that when these individuals were apprehended in the early hours of the morning, there was no way to transport them to jail.

At that time, the only senior law enforcement official in Orleans was a man named Constable Perry. Knowing that they had to do something with these offenders, Perry created a makeshift holding cell in the front bedroom of his home.

Today, that home is the location of the Jailhouse Tavern, one of the more unique places to enjoy a drink or meal on Cape Cod. The venue has a speakeasy feel to it, but rest assured, as it's completely legal and a trendy location for Orleans locals.

A Look at the Atmosphere

As you approach the Jailhouse Tavern, you'll see that part of the restaurant is in an old stone building. This building was Perry's house. 

While there are now additions to the property, the main dining room sits in the old house and features period furniture and jail bars on the windows. It's like stepping back in time to the Prohibition era and enjoying your evening in a jail-themed speakeasy in Orleans.

Of course, there's more to the venue than the old stone building, as you can also have a meal in the dining room, have a drink by the fireplace, or spend your day on the patio.

Overall, the Jailhouse Tavern is a throwback from the 1920s that isn't to be missed after moving to Orleans.

What's On the Menu?

Of course, you'll want to know what the menu looks like before visiting the Jailhouse Tavern, and the good news is that there's a little bit of everything.

The appetizer menu has things like crab cakes, nachos, wings, clam chowder, and salads. The restaurant has burgers, fish and chips, tacos, and lobster rolls for lunch, while for dinner, the menu expands to include seafood, steak, and ribs. There are also vegan options at the Jailhouse Tavern.

When looking for a drink, you should know that the Jailhouse Tavern has a full menu of spirits and can make any cocktail you're in the mood to try. They also carry a rotating lineup of craft beers on tape and have an impressive wine list, as well.

How to Get There

The Jailhouse Tavern enjoys a convenient location on West Road in downtown Orleans. The historic house is pretty close to where Route 6 and Route 6A cross paths and is just up the street from Skaket Corners. It isn't in the heart of downtown, but it's close enough that you can walk there from many parts of Orleans.

The tavern shares its building with Hog Island Brewing Company, too, so you can head over for a beer before or after your meal.

You'll have plenty of options when seeking a wonderful dinner in Orleans, but few locations have the history and atmosphere you'll find at the Jailhouse Tavern.