Jailhouse Tavern

A bit pricey. Great atmosphere. We had the chili, very spicy but good. Cheeseburger was tasty, could have had a bit more fries for the price. Oysters were fresh. Sliders were good also. Two things that are worth mentioning… why is your lobster roll made with Maine lobster, there aren’t enough lobsters locally? And lastly the woman at the next table ordered a cappuccino, the waitress came out with black coffee in a Irish crème coffee mug topped with whipped crème. Really? When the woman questioned the waitress she said their machine was broken and she thought that her homemade substitute would be all right, seriously? Overall our visit was good.

Lobster mac n cheese was amazing! Excellent margarita and chocolate lava cake. Great atmosphere, can’t wait to come back in the summer and play some corn-​hole on the lawn out back.

We almost passed by this restaurant because of old reviews. So glad we decided to take a chance and stop. It was clean. Service was great. Drinks and bread came right away. Harvest salad, meatloaf, and short ribs were all excellent. Nice atmosphere even though place was bit dark in middle. Jazz band plays every Wednesday night off season which was added bonus.

Great bar, friendly service and a good value. Jailhouse is a step above bar food and they have an exceptionally good children’s menu. The only drawback is that they wipe the tables after every diner with the nastiest smelling, ammonia based substance imaginable. Instead of enjoying the smell of your food, you get to enjoy their cleaner. Not

Had an amazing birthday dinner here! Great staff and service, cocktails were amazing! My food was delicious. Perfectly cooked gluten free dish. The chef even came out to help me with my selection because of my allergy.
I met both owners and they have a great vibe. Easy going laid back and attentive, exactly what I would expect for a Cape Cod experience!
Awesome people and a great place to go!

I went to Rock Harbor Grill tonight, as a single woman. The bartender there was downright rude. I left and went over the to Jailhouse. A very pleasant bartender made everyone feel welcome and what a bartender should be!

Had dinner at the bar for the first time this year. Jailhouse now has a very nice selection of beers, including a Jailhouse Lager. The new menu was terrific with good variety of offerings. My husband had the mussels which he couldn’t say enough good things about, in between bites. My Cape Cod Reuben was excellent as well. Jailhouse has upped its game. It has always had good food– now it’s exceptional.

We had a large party, and service was good. The food was great, I had the best Fish Reuben ever! A friend got the clam pie and she can’t stop raving about it.

If you’re looking for a place for a large group, this is it. There were 20 of us. They don’t take reservations, but they knew we were coming. We got there at 6:30 and all had drinks at the bar until the table was ready at about 7:00. The ambience was great, loved the stone work and all of the lights they had hanging up. It felt really clean. We had one waitress and she did a great job! The appetizers were great– especially the Blue cheese chips if you love Blue cheese like I do! I had the Codfish Picatta served over potatoes. My husband had the fish tacos and those were yummy too! The portions are generous. We all had a great night! Happy that we chose that spot.

Very over priced.
Ok, so I get that this place has become a tourist trap but really, $ 17.00 for a very average salad?! As a vegetarian I’m often limited at seafood/​steak places which is fine but the few options I had were needlessly expensive. This place is too casual to command $ 25-​$ 30 entrees. I’ve been going to the Jailhouse for 10+ years. This new group of owners just seem greedy.

Stopped in for dinner on a Wednesday night while we were staying in Chatham. Upon sitting down, we realized there was a dirty cloth napkin under our table which we had to fish out. We began with the Lobster corn fritters as an appetizer. It came with a spicy aioli sauce. This consisted of 6 large fritters that were tasty and a good start to the meal. The sauce had some kick to it.
Our table ordered the tavern steak sandwich, the cheddar cheeseburger, and the black bean veggie burger. We were allowed to substitute the fries for a baked potato or vegetable. There was a small $ 2 charge to substitute.
I was disappointed with my steak sandwich. It was smothered in onions and mushrooms which was ok. There was much more onions and mushrooms than needed and it was almost like they were trying to hide the poor, thin cut of meat. Very dry. It was served open faced. My wife and daughter each liked their burger and the sweet potato fries on the veggie burger were a big hit. The veggie burger came on a sandwich flat which was a nice touch. We had to ask twice for ketchup after our burgers were served. No room for dessert.
The service was very friendly but spotty. Our waitress was hustling and we noticed she had tables in the bar area as well. It didn’t appear they had enough people working. The bar area was very charming with the stone background and the black bars resembling a jail cell. The bathrooms were clean and there is a big parking lot out front. The lot is darker than usual at night and could use more lighting. Decent spot overall.

As a local resident I was extremely pleased to experience another excellent restaurant in orleans. I think the upgrades to this establishment were all around great. The ambiance and service is a little more upscale than before and comfortable and casual at the same time. The food was awesome, my husband had the linguine with clams, my daughter had the macaroni and cheese and I had the short ribs. Everything was excellent. I also feel the cost was on point with the quality of the meal. I also noticed a fun atmosphere out back when we were leaving; a band, corn hole on the lawn etc. Really happy for this place and plan on going back.

When I arrived at the Jailhouse Tavern, I was immediately struck by the cool combination of Cape Cod charm with the stony arches of the actual, revamped prison. My party of 4 got there at about 6 PM, were told that there was a 20 minute wait for sitting inside and a 10 minute wait for outside, and opted to wait a little longer to say indoors. At 6:55, we were finally seated in a booth. Everyone in my party ordered immediately and we still had to wait at least 30 minutes before our appetizers came out. If we didn’t have the bread basket to tide us over, I wouldn’t have been as forgiving about the delay. The crab cakes were delicious! Crispy on the outside, moist on the inside, and paired perfectly with a mango salsa and the best tartar sauce I’ve ever had! I wish the portion was larger than just two! The steamers were also good. As a native New Englander, I thought the clam chowder was on par, but a little skimpy with the clams.
I ordered one of the specials, a coffee rubbed flank steak with cheddar mashed potatoes and mixed vegetables. It was good and I enjoyed it, but it wasn’t spectacular. I wish the steak had been a little more tender and juicy to balance the dry rub. The flavor was good though! I also think that the cheddar mashed could have used a little more sour cream or something to make it less dense.
What makes the Jailhouse Tavern merit three stars was the combination of the too-​long wait to be seated and served (and the fact no one apologized!) more than the food itself. The ambiance was great; I wish I could have heard the live band on the patio from inside! That being said, the ONLY reason I’d come back would be to sit at the bar inside the cool old jail and have a few crab cakes.

I’ve been here several times and am always satisfied. Good food and good service.

Super dinner and attentive waitstaff. Price was reasonable as well. Would recommend to friends.

Maybe the owner is new but this place hasn’t changed a bit! The service was terrible and food even worse! No ambiance at all and pricey for lack of quality in all areas. A below average experience!

Cisco brew beer, clam pie and meat loaf! Everything was fresh and good sized portions. Friendly service and nice atmosphere. Great spot for lunch or dinner on the Cape!

If you drive past this place turn around and head in. Right off the bat you can tell that it is going to be good. If the place is clean, the beer and food follow suit. A very friendly bartender (Juliet) greeted us warmly and had coasters down to take our drink order. Must haves… Cape Cod Beer… duh. It’s fresh and amazing. Both of our sandwiches were huge and delicious. I don’t think we took resting breaths between bites. She had Ruben juice dripping down her arms all while wearing a chipmunk smile. A fantastic experience.

We just dined at the Old Jail House for the first time, and we were both pleasantly surprised. I had the Clam Pie, a vanishing traditional Cape Cod favorite. She had the Baked Cod. Both were very good. The bar was good, not great (Tribuno vermouth…) But they had a good lineup of local beers on draft. The server was knowledgeable and pleasant. The atmosphere was low-​key, which we prefer. We’ll be back.

I can attest to the slow Bartending staff and the delayed food service. The food was decent with the quahog being $ 7 for a small shell of a quahog. The flavors made up for the tiny portion. The fish piccata had twice as much potatoes as fish, but still good. $ 25 for piccata was a stretch seeing that the cost of the small portion of fish was at best $ 6.00.
I hope this place continues to improve and they can take the reviews as ways to strive to be better.