Harrie's Jailhouse — Restaurant in Middletown

This was surprisingly underwhelming. I'd bookmarked this place literally years ago - I don't know how I would have stumbled across it since it's in a section of CT I never go to - probably because of the unique vibe, menu and strong ratings. It felt like fate though when I ended up coming this way with one of my best chums who literally went to the school of hospitality on our voyage to Boston. She loves these kinds of sandwiches/comfort food, and I like historic shizzle and mixology. How do you not stop by under those circumstances?

Part of the problem may have just been timing. From the pictures it seems like the best area to sup in is upstairs, but it was closed off when we came by on Saturday afternoon so we had to sit in the basement bar. That was fine, but it wasn't the preference. Also keep in mind the weather was TERRIBLE - it was cold and rainy and 100% may have been a factor here as well. There was some personality to the basement but not as much as I expected, honestly. It was a mostly brick interior, with some framed pictures of ye olde felons, etc. I think again because of the weather it just felt a little damp/meh in there, and there's not a lot you can really do about that - that's the risk of having a basement business, I suspect.

I went with the Maple Chicken sandwich, minus the arugula and onions. It was fine; I always like the extra effort of the pulled chicken on a sandwich like this, which was probably my favorite aspect. I think it really needed some kind of condiment because it was definitely on the dry side - the maple bacon jam didn't really do anything in the moist department, and as a personal texture-based palate preference, I wasn't crazy about the random crunch of a bacon bit in there. The maple definitely paired well with the chicken though, and the flavoring was solid.

For my cocktail, I decided it was too early to go down the bourbon rabbit hole and opted for the Lights Out, which featured mezcal and elderflower. I was a bit underwhelmed by that one. I'm pretty ambivalent about mezcal, but I thought it was too dominant in the drink and basically gave the whole beverage a gasoline vibe, which...that's definitely not a first cocktail of the day situation.

The service was just okay. We were greeted by the bartender immediately and she did stop by once or twice but it was on the slow side for sure. There seemed to be another person helping with bussing, etc., but she was handling the lion's share of responsibility, which included being the only bartender and the primary waitstaff. I imagine it's a tough call to decide on the appropriate amount of employees on a rainy Saturday afternoon versus the evening shift, but it was pretty apparent they needed one more staffer on the premises. It took a while to grab the check and have same processed.

I'm not writing this place off but if I happened to be in the area at a similar time of day and/or weather situation, I'd probably...

October Update! We went to Harrie's Jailhouse for dinner upstairs this time. We had a 5:15 reservation and the place was already buzzing. We ordered the same thing as our first visit in January (see below) with the exception of the PB/chocolate dessert which was incredible! Upstairs still has a cozy feel, yet more open and less "tavern-like" than downstairs. Shout-out to the servers who hustle on multiple levels to get food to the tables and keep customers happy. Our busy server even took time to take a photo of us - thank you! January 2025 - Finally made it to Harrie’s Jail House restaurant in Middletown! We arrived on a Saturday around 1:30 and were directed to seating in the basement as the upstairs takes reservations for dinner only. The downstairs has a cozy vibe with a variety of tables at different heights and an L-shaped bar. With lighting on the dim side, we sat at a table next to a window. Our waitress was also the bartender, so we were very patient as she juggled drink orders with food orders like a pro! The menu has a nice variety of options that all sounded so good we know we’ll be back to try them. I had the “Sanguiche” sandwich with two huge pieces of crispy thin eggplant atop, turkey, salami, ham, provolone, roasted red peppers, lettuce, tomato, Italian dressing, and fig jam served hot on a fresh grinder roll. D-E-L-I-S-H!! We shared the “Two’Fer” platter of super thin, crispy onion rings and French fries with two dipping sauces – so good you have to make yourself stop eating them, or not! Parking is tricky and they do talk about that on their website under the “More” tab. The sidewalk to the basement entrance is wheelchair/walker accessible with a few uneven surfaces here and there. Once inside, it is narrow for a wheelchair, but doable (I would call ahead). Already looking forward to our next meal at...

It was our first time. I have been intrigued to go when it was another restaurant because of the history of the place and the actual poor house behind the restaurant was supposed to have sightings of a small girl for those that believe in such. We never made it to the previous establishment due to the world shutdown. But let's discuss this one..we parked in the back and walked up to the front thinking that's where we would be given a choice of inside or out..there was a chalkboard with directions to proceed to the back..outside..which would have been our choice..so idk if there is inside dining in the main house or not..patio area was nice..it was early 4:30 so we were alone..the bar is located in the basement..I didn't go in but hubs did for the restroom..menu consists mainly of sandwiches but not run of the mill..it was quite difficult for me to choose as they all sounded delicious..hubs had to take half of his home..he had the sanguiche..cocktails have simple syrup made on premises and I had "drink the roses" really quite fantastic..he had Medusa draft beer..it's a casual place but atmospheric and out of the way at the same time..could be because of the time we were there..check out the menu online before you go..waitstaff smiling and polite..we will definitely be...