Certainly an interesting restaurant, tucked away in the middle of a less-than-pretty road, which somehow makes it even more intriguing. I do wish there were more signs, as both the parking lot and the entrance felt a bit vague and easy to miss. Once we finally found our way inside, we were pleasantly surprised. The atmosphere reminded me of another local tavern. Staffed by friendly people. The food was good, and the overall experience was enjoyable. My only disappointment was the lack of information about the history of the establishment. There is a lot of marketing that references its connection to a jailhouse on the menu, but very little information is actually shared within the tavern itself. I found myself wanting to learn more about the story behind the place. I also think it would be fun to add a photo-op area--perhaps even outdoors--with a set of mock jail bars where guests could take pictures. It would fit the theme and add a memorable touch. The tavern itself is fairly small, so I can imagine it gets quite crowded during busy times. Overall, it's definitely worth checking out. read more

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We really liked it. The Cuban was authentic and well done. The club was amazing. The onion straws kinda greasy. We also tried their buttery and spicy Chex mix. It was buttery not very flavorful. Interesting layout. Fast friendly service. We were lucky when we went but not sure about parking options. read more

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Gave a gift of the Midsummer Garden Party to a couple, and they absolutely loved it. It included two drinks per person and appetizers all around. The food was very good and the gin cocktails were a lot of fun. Everyone was really friendly . read more

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When we travel to a new place, we always look to Yelp to find a good place to eat... then, we try it and leave our own review. This place was a real standout. It's a very small place... more like a bar but with outstanding food. The building itself is super cool and the vibe inside is great. The Southern BLT with a fried green tomato (this was great) ... also the arugala salad with goat cheese and other goodies was so good. The grinders were huge ( big enough to share) We were so happy we stopped here. Was the best lunch of our visit here ... and the folks were very friendly read more

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You need to come eat and drink even NA All of the food on the menu has been great every time we come in their homemade drinks are great as well even if it's a non-alcoholic homemade lemonade fresh squeezed at the bar for you then whether you sit in the basement or upstairs or even outside on their patio area such a nice area great service all of the staff is friendly and helpful read more

I loved this place. Overall vibe was neat even though it was extremely random. I loved the fried deviled eggs, just wished for a larger portion--especially when sharing. The MacArthur sandwich was really good and different. Not too often you come across cold asparagus on a sandwich but I enjoyed it. Service was good, nothing special. read more

Harrie's Jailhouse - The MacArthur - Sandwiches Near Me - Middletown, Connecticut

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I almost don't want to say how great this place is because once it goes out on TikTok- it will be packed. Inventive, creative pub food that was perfectly prepared. Eggplant slider was the best eggplant parm I have ever had. Fantastic food, great drink menu in one of the weirdest locations. Can't wait to go again. read more

I was looking for somewhere new to meet up with a friend. I found this place on yelp and thought we would try it out. It looks like a regular house and you can park on the street or the driveway and park in the back. There is outdoor eating and patio in the back and the restaurant itself is the basement and the entrance is in the back. When we arrived, we went early, so there was nobody there however when we left the place was full inside and outside. It is dark inside like a bar, but is very welcoming. The waitress was very nice and helpful. My friend ordered disco fries and very much enjoyed them. I ordered the southern dippers which came with fried green tomatoes and fried pickles along with three different sauces. I enjoyed all of them however I particularly like dill, pickles, and not sweet. These pickles are on the sweeter side however I ate them and they all tasted great we both got an eggplant slider. I thought the slider was very tasty. It does not have much on it. It has a sauce on the top and sauce at the bottom however, when eaten together, the flavors mix very well. Overall, I was happy with my meal. We both said we would go back and try other things. read more

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A great place to enjoy happy hour! For happy hour, they have so many great options ranging for $9 drinks, $4 sliders, $3 chex mix, $10 flatbread pizzas and more! Their chex mix that's seasoned and buttered was the perfect starter. Their street corn flatbread was fantastic - a unique combination that is right up my alley! We also tried one of each of their sliders. My favorite was the chicken cutlet with pimento cheese, it was tangy and savory all in one. The french dip slider was also a stand out for me - the meat was tender and the au jus was tasty! The eggplant one had a really nice black garlic mayo on it, however, I felt like their could have been more eggplant as it a lot of bread. We ended off with their peanut butter s'mores and their homemade marshmallows are so impressive and amazing!!! read more

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Another great experience at Harrie's! We waited 20min for a seat outside, and got a drink from the cool basement bar while we waited. Drinks came out quick and were great. We started with the sliders, a perfect appetizer for two people. We each got to choose one slider for ourselves. I got the special, a chicken caprese sandwich. It was delicious!!! I love how thin and crispy their chicken is. My boyfriend got the turkey club sandwich which is really enjoyed. I really do love coming to this place. read more

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Harrie's is in an old jailhouse that's rumored to be haunted. That alone is a draw for me! I like sitting in the basement bar area. I prefer the vibe there. They are open daily now and have happy hour weekdays from 4-6. Great happy hour prices and it gives you an opportunity to try many different things. I ordered a deviled poppers, eggplant slider, chicken cutlet slider and what they call a twofer (onion straws and French fries). Everything was really good. If you like deviled eggs their deviled poppers are a must try! I'm am also sucker for their onion straws. I also had an espresso martini! Yum! I ordered a bag of their house made Chex mix to go! They have a pretty expansive menu of different sandwiches, there's something for everyone. Service was good, server was attentive. read more

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Decided to check out Harrie's on Sunday evening and they had a reservation available. Only the downstairs was open, which was fine for us since we had a small group. Our server was super friendly and very helpful in making decisions and checked on us without hovering. It was pretty busy but not loud or cramped. I had the seasonal salad and was surprised that it came out on a sheet pan as I have never had/made a flat salad before, but honestly it was a good idea since everything gets topping and dressing this way. We shared a pot de creme for dessert (it was really more of a mousse) which was yummy. I also had the seasonal warm cocktail which was deeelicious. Cute spot, good food. read more

It just gets better and better every time I come here. They have fantastic sandwiches appetizers and really good drinks. The service is always on point as well. Always a good experience. read more

Harrie's Jailhouse - Deviled eggs - Sandwiches Near Me - Middletown, Connecticut

First time here and food was great. El Warden had spicy tequila (which I've never tried) with a spicy chili lime salted rim and had the kick to start the night. Sat in the basement bar On the downside, I was expecting a renovated "jail" as is was the old Pamecha jail from the 1850's, instead the lounge area inside only contained a wall and old steel hinges where the old cells once were read more

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Came here upon hearing the hype. It's not worth the reputation. The food was very expensive, even more so than most other restaurants these days. The biggest issue with the food is that it's not a lot and everything extra costs. I got the BLT, which tasted alright (shouldn't be the excelling factor for a place you go to eat). The sandwich took 20+ minutes to cook and came out with 50% stuffed with lettuce, 2 thin strips of bacon, and a few tomatoes. For $16 you only get the sandwich of the caliber you can make at home. Additionally, if you want any "sides" with your sandwhich you're looking at forming over $4 per side per person. This place is seeking to charge as much as possible and give as little as possible. Beers were also $8 for ~8oz glass. The staff were nice, but a tad pushy. They kept trying to get us to buy more stuff rather than acknowledging what we ordered off the bat was all we wanted. The atmosphere too was very overwhelming. They put you in a small, dark bar room with cramped tables and low lighting-- despite it being the middle of the day and sunny out (no outdoor seating). The music was blaring loud despite the room being so small. Overall the vibe was stressful. Simply put, you come here if you don't care about money when dining. It's not as great as promised read more

Harrie's Jailhouse - BLT - Sandwiches Near Me - Middletown, Connecticut

I had such a great time at Harrie's. We ate in the basement. We had a great time. The place is clean, the vibes are so chill. The food was super hot and fresh. We had no issues with anything. Server was incredibly attentive and sweet. We would absolutely go back. 8.2/10 read more

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If you're like me you expect every restaurant in Middletown to be on Main Street. Well this is the exception. Driving here you'll think someone sent you to a residential neighborhood how this building is situated. Nice outdoor patio area surrounded by trees and multi family homes instead of cars and commercial buildings - it's a nice change of pace. The lower bar area is super chill. Feels like the kinda place you gotta know someone to gain entrance to. Lots of regulars at the bar. Service was great. Everyone was friendly. Food and drinks came out fast. The wings were good but the flavors were so so for us. Don't waste your time on the wasabi flavored ones. Cocktails were good too. Small selection of liquors but solid choices. Overall a fun hole in the wall. This review is more like a 3.5 for me. I would return but there are so many options in the area nothing is making me put this ahead of trying somewhere new or visiting an old reliable restaurant. Come check it out, I'm sure you'll enjoy the chill vibes and home town feel. read more

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Cool little basement place with a warm fun vibe. Sandwiches were excellent and service was excellent. If fireplace or something, I'd never want to leave read more

Looking for a unique and superior dining experience off the beaten path in Middletown? Harrie's should absolutely be your next try. And when I say, off the beaten path, I mean it's pretty easy to miss, nestled in a residential neighborhood a little ways away from downtown and Wesleyan campus. I've been twice now, both different dining experiences. The first time was at the bar downstairs for lunch. Shared some apps and I had the Huntsville Beef. All amazing. The bartender was great. Downstairs is the jail part of the jailhouse and has a very cool vibe. It was mellow when I went the first time, but jam packed when I came back and ate upstairs. The mixed drinks are creative and crafty with homemade ingredients and seasonal specials. The tap list is not expansive, but totally sufficient. There's something for everyone between the taps and the cans. The second time was a Saturday night and we got reservations which puts you upstairs. The dining room is cozy and also has cool vibe, being the house part of the jailhouse. The service was quick, friendly and attentive. This time I had The Sanguiche with Mac and cheese on the side. Wowza. An explosion of flavor and textures. Brilliantly done. The Mac and cheese was great too. We had a shared desert - a cherry hand pie. Soooo good. Like a gourmet 80's McDonalds cherry pie. In the scheme of things, I feel like Harrie's is pretty affordable. It's always a nice feeling when you feel like you really got your money's worth. I'm looking forward to getting back here in the summer and eating outside. I wish they were open for Sunday brunch. It would be a perfect brunch spot. read more

Harrie's Jailhouse - The Sanguiche. Brilliant explosion of flavors. Whalers Pale Ale. - Sandwiches Near Me - Middletown, Connecticut

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If you're looking for a unique dining experience in Middletown, I highly recommend Harrie's Jailhouse. The atmosphere is a historic jailhouse setting creating a fun and memorable experience from the moment you walk in. The food is excellent, featuring creative comfort food and delicious sandwiches, while the cocktails are expertly crafted and always on point. The staff is friendly, attentive, and makes you feel welcome. Harrie's delivers great food, great service, and an nice atmosphere. Can't wait to come back! read more

This is a Cool little restaurant! History has it that this use to be a small jail in Middletown and is possibly haunted. The Food here was good I ordered the jailbird chicken sandwich. The Drinks were delicious too! I ordered the el warden! It was the perfect combination of sweet and spicy. read more

Harrie's Jailhouse - Jailbird sandwich - Sandwiches Near Me - Middletown, Connecticut

Kind of hidden, and difficult to understand access. We went for lunch on a Saturday afternoon and the upstairs was closed so a chalkboard sign directed us around back, to a basement. It was dark and there was really no indication that this was ever a jailhouse. We each got sandwiches that were too big for some in our group and too small for others. I ordered the Huntsville Beef, which was good, but bland. Never in my life did I previously add salt and pepper to a restaurant meal, but this needed something. Even at $16 for a sandwich, they charge extra for fries or chips! The beers were also overpriced at $8 for a small 8oz glass of Elevated. Napkins were real cloth, not the typical disposable paper ones and that was a nice touch. Maybe the atmosphere is better upstairs, but we will never know. read more

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 look elsewhere. read more

Harrie's Jailhouse - Lights Out. - Sandwiches Near Me - Middletown, Connecticut

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The best wings I've had in years and I'd say they are better than J Timothy's in Plainville. The drinks are creative the burgers were cooked perfectly and my wife had a half sheet pan salad that was enough for the both of us to share! read more

yes, Yes, YESSSS!! To find a place like this on an obscure side street in Middletown was one of the best moment since we moved here (neighboring town) during 2020. Ok... ambiance 10/10, service 10/10, food 10/10... just perfect. We had Brussels sprouts, a wedge salad (best one ever!!), a chicken cutlet sandwich. This. Was. The. Best. Very thin, crispy, just salty enough and then the craziest Green Goddess dressing on this thing. DEAD. Soooo good. Brava... will be back. Huge fans! read more

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Only my second time. Line was long for waiting but didn't take as long as we thought. Food was good. I had turkey dinner. The stuffing was more like croutons but I added cranberry sauce and some gravy. Brussel sprouts were not cooked enough for me. I had trouble biting/chewing. My teeth are moving with the help of Invisaligners so teeth very sensitive/painful but once a took home and cooked a little longer they were good. Turkey and potatoes were fine. My daughter lover her meal. I like the place and our waitress was great. What a hardworker. read more

Love this place Good menu in a very comfy atmosphere Friendly staff. A surprising place in a Middletown neighborhood read more

If you can find it, you'll be thrilled!!!! The food! The drinks!!! The atmosphere!! They keep the selves hidden because most of us aren't magic enough to belong! The employees are SO fabulous!! Run , don't walk! read more

The happy hour food and drink specials are fantastic, even though it was a beautiful day we chose to skip the patio and go inside downstairs and try the old jailhouse seating, it was very cool, our server was great, and I'm already looking forward to going back. read more

Very interesting place . Cute old house hard to imagine that it was a jailhouse! Our waitress was nice and helpful. I had the honey siracha wings my friend had the burger. I had a yummy drink but I can't remember the name of it. I would definitely go again to try more on the menu! read more

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My friend and I were at Lyman Orchards for Evidence of Evil, after that we wanted to stop somewhere for a drink, I suggested we go to Harrie's Jailhouse, since that's an easy drive. Harrie's Jailhouse is an adorable spot. I actually sat in a different area then the last time I was there. So I got a different perspective of the place. The ceilings are so low, and they have exposed brick everywhere. It is truly so cozy to be here on a cool evening. Since the kitchen was already closed when we got here, we just had some drinks. I got the Pameacha Punch. This is like a Moscow Mule, it had the base of dark rum, a few juices and ginger beer. It came in a cool Tiki mug. I loved my drink, it was cool, refreshing, with a light kick. I really love the ambiance of this place. Their food is Devine, but we didn't get any this time. read more

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Not worth the trip. Vodka selection sucks. Not worth the price your paying for food or drinks. Martini glass was half full. read more

This place is in an old jailhouse I guess. It's really cool. Awesome vibe, great food and specialty cocktails. Food and service was great. It's a bit small so get there early upon opening. read more

Harrie's Hailhouse is a gourmet pub that opened in Middletown, Connecticut in March 2021. It was founded by business partners Carrie Carella and Heather Kelly. The historical structure that houses the new restaurant is the former Pameacha Jail. The vintage 1850s Victorian structure used to serve as a jailer's residence. Twelve cells of heavy brownstone used to extend beyond the back of the house, but were carted away when the jail closed around the start of the 20th century. Two brownstone walls of the original cell block remain intact. Bread and Water Restaurant called the location home for several years until it closed due to a devastating fire. Carella was general manager at Eli Cannon's Taproom for 15 years before opening NoRA Cupcake Company in 2011. Kelly began working for Carella in 2015 and soon became the operations manager. Once the Pameacha Jail location became available, the partners decided to open a completely different concept. The new venture features hearty sandwiches, housemade bar snacks, and classic cocktails -- all with a twist! My family and I recently visited Harrie's for October brunch. Brunch is served the first Sunday of every month, and an Autumn-themed brunch sounded delicious to us. We were seated in the basement bar. For cocktails, my wife had the "Harvest Spritz" and I had the "Basic & Boozy" (SoG cold brew, Jameson, rumchata pumpkin spice, cinnamon whip cream). Both tasted like 'Fall in a Glass'! We all shared a delicious plate of "Devil Poppers" (crispy & spicy deviled eggs with bacon & jalapeños) which disappeared very quickly. For entrees, our son had the "Pumpkin Pancakes" (cinnamon maple syrup, side of berries), my wife had the "Chicken or the Egg" (chicken cutlet, scrambled egg, provolone, lettuce, tomato, red onion, green goddess dressing, 10" roll), and I had the "Benedict Bake" (egg soufflé baked with Black Forest ham & English muffins, topped with hollandaise & scallions, served with a side of balsamic dressed arugula). My wife and I also ordered sides of "home fries". Everything was delicious!! This wasn't my first time at Harrie's and it certainly won't be my last! read more

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Spoiler alert. Harrie's Jailhouse really was a jailhouse before it turned into a hip, elevated sandwich, salad and app hotspot. I've been aware of Harrie's for a while, but I didn't know where it was in Middletown. Turns out it's in a residential-looking area not far from Neil's Donuts. Didn't see that twist. Another spoiler alert. This is a 5 Star review, although the food itself was closer to 4 Stars. Don't get me wrong. The food was good. My wife and I shared the Disco Fries and I ordered the Sanguiche. The fries themselves were good. They were topped with gravy and a cheese sauce. Both sauces were good, but nothing here popped for me like the best versions of similar dishes. The Sanguiche is in the Italian Combo Grinder family, but it had some differences that intrigued me as I scanned the menu. In addition to familiar items like salami, ham, lettuce, tomato, roasted reds, provolone and Italian dressing, it had turkey, fig jam and crispy eggplant. As with the disco fries, the sandwich was good and looked great. I just didn't connect with it like the best versions of this type of sandwich. There are plenty of other intriguing sandwiches on the menu that I'm sure I would connect with. My wife loved her mix and match sliders for instance. So the Food was a 4 for me, how did Harrie's get to 5 Stars? Three reasons. First, our server was one of my favorites in recent years. She was friendly, funny, personable, efficient, knowledgeable and interested. She should teach classes. Second, the outside dining area was very cool. They had layers of umbrella protection, comfortable wood tables and an outdoor sectional. And guess what? It unexpectedly rained. Didn't matter. Didn't get wet. Umbrellas. Third, we had fun. At lunch! They were playing fun music that we later learned was from Apple's Summer Soul Playlist (A+ server investigated for us). We were singing, swaying, etc. Etc. The food doesn't have to be the best ever to earn a 5 Star review. It has to be good, and it was. A restaurant can get there with top notch service and cool atmosphere. read more

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Both the food and drinks were delicious. This restaurant offers outdoor seating in warmer months.

First time here late night, service was excellent despite being so busy. I love the overall vibe and ambiance of the basement bar and the fact this restaurant is set in an old house is so cool. Definitely a trendy place but lives up to the hype! Ordered some draft beer and the BCP, buffalo chicken poppers basically. So delicious! read more

Harrie's Jailhouse - Sandwiches Near Me - Middletown, Connecticut

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Excellent food, atmosphere is great for a date night upstairs. Not sure how downstairs works, but seemed very lively.

The atmosphere was good. We sat outside. I wish I could remember the name of all the dishes. We had a dish that was like a breaded deviled egg top with jalapeños. I have the steak and cheese sandwich. My friend had the buffalo chicken fries. The lemonade was pretty decent. read more

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We had apps that were amazing. French dip sliders, eggplant sliders. Cucumber gazpacho & fried green tomatoes. Really fun flavor profiles & nice & cool in the bar. Starting to be a favorite place for sure. Thank you, Heather! read more

Harrie's Jailhouse - Freaky Tiki cocktail - Sandwiches Near Me - Middletown, Connecticut

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