Delicious comfort food and great cocktails in an historic setting. The service is stellar as well. Try the short rib melt and the seasonal cocktails! read more

Stopped in Harrie's Jailhouse for a drink shortly before closing. This is an unassuming "house" on a residential street. I had been wanting to try this place and we were looking for a place to get a nightcap before heading home. We are so glad we came. Our waiter/bartender (I think his name was Justin or Josh) was so much fun. The kitchen was already closed, but we will definitely be back to try the wings and more drinks!! read more

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

See all

My family and I finally got to visit Harrie's Jailhouse. We are normally a family that eats our meals at regular times, so with an opening time of 3:00 pm we decided to make it a lupper - late lunch/early dinner. When we arrived, we were the only patrons there. We had our choice of table, so we sat inside by the fireplace. We were greeted by our sever and brought a bottle of water for the table. It only took me a minute to decide on the Devil Poppers, a fried deviled egg with jalapeño and bacon. My MIL and I decided on the Jailhouse Fashion and Thymes up to sip while waiting on our food. I would've expected to see soda, iced tea or lemonade for those not drinking from the bar, but there were no non-alcoholic drinks on the menu. My husband and son ordered The Clubber, my MIL ordered the Sanguiche and I opted for the Southern BLT. The sandwiches are served with house made pickle slices...about 4 or 5 to be exact. All sides are extra, ranging from $2.50 (more pickles) to $5.00 (mac 'n cheese). When ordering a sandwich in the $12-$17 range it would be a nice touch if the sandwiches were served with a handful of homemade chips or a small scoop of coleslaw. I would also like to mention that we did not find this menu to be kid friendly. There is not a kids menu and the portions are definitely for an adult. As well as the before mentioned lack of drink options. That being said, my Southern BLT was Amazing! Made with fried green tomatoes, slab bacon and tomato jam on grilled Texas toast, this is a must try! I also added the coleslaw as a side. The portion was decent and it wasn't to sweet, just a little wetter than I prefer. My husband was less enthusiastic about his Clubber. It was a pretty standard club sandwich. He did order a side of fries and he enjoyed those. My son loved his sandwich and he said that he would order it again. My MIL like her Sanguiche. We decided to swap off a half of our sandwich. Both of us agreed that mine was awesome. We were little disappointed in the dessert menu. With only two offerings, we chose a S'mores bar for the table. Owned in part by NoRa's cupcake queen, we had expected to see a NoRa's cupcake option. When asked, we were told that they were trying to separate the two establishments and show that there was more culinary talent to be shared. We did not miss the cupcake and were all thrilled with our S'mores bar. Unfortunately, this was eaten before I could snap a picture. I'll definitely be visiting again. I might even try something different...who am I kidding?! I'm going back for the Southern BLT! read more

See all

Wow! Such a Cool Place to Hang out with friends and have an Awesome Time. Hey, If you're Really Bad maybe you can decide to dine in the jail cell if it's available. They have a great patio outside for when the weather is nice. Since it's located on a residential street parking is mostly on the street. The drinks are great the bartenders are really friendly and welcoming happy to give you suggestions or make something up for you. I went with Two-fer it's French fries and onion straws with their house made buttermilk ranch and harrie's sauce. It was huge so as I said it's a great place to bring friends. I chose the Southern BLT....it's got fried green tomatoes on it and pimento cheese. It was absolutely delicious. The hubby chose the Sanguiche basically an Italian Grinder fancied up with some fried eggplant and fig jam and it's served warm. We split each sandwich and were reluctant to share because we each thought our choice was good and then when we switched we thought the others were good too. I don't think you could really go wrong with any of their items on the menu. We didn't have room for dessert maybe next time since their desserts are for Nora's so they are bound to be delicious also. read more

See all

Cool little local spot! Hearty, comfort food. Unconventional atmosphere and good vibes. Enjoyed a few meals at Harries but haven't remembered to document our visits. More to come! read more

Barria tacos were awesome along with the consommé and puréed jalapeños that were served with them. Hope they stay on the summer menu

This place is a hidden gem! A bit hard to find since it's in a residential neighborhood with limited parking but worth the effort. Came for lunch and sat downstairs. It was crowded and we grabbed the last table available. Went with the gin & jam cocktail and haven't stopped thinking about it, yum! For food, I ordered the Sanguiche which is similar to an Italian combo sandwich but with fig jam and eggplant. It was delicious. Will be back! read more

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

See all

Great ambience in the downstairs bar. To start we ordered the southern dippers. It is fried green tomatoes and fried pickles. I had the special, chicken cutlet with house made peppers relish and arugula. My husband had the jailhouse grinder. Both were of size. You have to pay extra for fries, onion rings, salad or chips. The only thing I'd suggest is to have more than one brand of vodka! Only Tito's here. I know it's a popular name but I'm allergic. I love a good vodka martini but it must be with grain based vodka and not potato vodka . Absolute, Stoli or grey goose. Otherwise we'd definitely be frequent customers. read more

Came by this cute little place this weekend with a friend. The ambiance was very nice and we both enjoyed our drinks which were made perfectly. The food just didn't hit for me, unfortunately.. I had the sanguiche and the fig jam that comes with it was just too overpowering and took away from the tasty Italian meats that I love. I got no flavor of mortadella which is my favorite meat of all time. There was maybe one slice of each meat on a HUGE sandwich. There should have been a bit more meat and a bit less bread. All in all, I think I just made the wrong choice of sandwich and would be willing to try them again if another one of my friends wanted to try. read more

Thank goodness for Yelp!! We never would have found this place! As a matter of fact we passed it and had to circle back because it's in the middle of a neighborhood. Also, if you are reading this and you like a great experience with food then don't go anywhere else! What an amazing environment. It's cozy and has a Victorian flare to it. There is a main level and downstairs bar. It's December so it is decorated for Christmas holiday. We decided to eat on the main level. I'm sure the bar is pretty cool. We decided to try the Devil Poppers (crispy deviled egg served spicy with bacon & jalapenos) first because the Yelp reviewers gave it high ratings. The first bite elicited a "Wow" and the rest was history! We also ordered the Wedge salad. Absolutely amazing. It has some great additions that will excite your palette for sure. We followed the above with the Big Butch Burger. It included two patties, Harries "sauce" , lettuce, tomatoes, pickles, onions on a brioche bun. Talk about flavor........ All in all this is a great find and needs to be explored by you!!! We will return! read more

What a Diamond in the rough this place is. If you weren't looking for it, you might miss it. Nestled in a neighborhood near Wesleyan University this gem of a spot is top notch. Formerly the original Jailhouse for the local PD, Harrie's puts out some great hand held sandwiches and burgers. The spot in the basement is a cozy bar with a hometown pub ambiance. The service is excellent and the whole experience memorable. This is comfort cuisine at its best. I highly recommend checking this place out. read more

What a fun surprise!!! Absolutely loved the vibe here, the old jail house and dark lighting . Sat at the bar and had great service. Highly recommend the fried deviled eggs! The blt also looked amazing read more

This was definitely not the easiest place to find at first .. Well this was definitely an interesting place . I was not a huge fan of their food . The burger sliders were good and the salad was huge . But definitely didn't like the fried zucchini soggy the Chex mix was a hit especially with the kids . We sat outside tables are very nice . The chicken skewers with couscous my son enjoyed . My roast beef a jou was not great soggy . Overall was fair split decision between the six of us . Enjoy Chris M read more

I'm giving this place 2 stars because everything single dish, cup, utensil on our table was dirty. The waitress and the bartender were extremely nice and great. We ordered sandwiches - I ordered the Rachel. Basic sandwich, no sides included, and I've had better. The restaurant itself has a very nice vibe to it and we saw pretty drinks coming out to tables around us but the dirty dishes will keep us away. read more

Restaurant inside of a house, that has a bar with a speak-easy vibe underneath it The food is all basic American grub with a sandwich-centric vibe I got one of their chicken & cheese sandwiches with a side of their Mac & Cheese. I was pretty underwhelmed as it was all very bland 6.5 read more

Came with the girls for dinner as we were driving thru the area and considering our line of work, decided to give this place a try. They were only serving downstairs and it was pretty full. We had a small high top by the wall. Not as much of a jail aesthetic as we thought there would be! Service was very spotty and it seemed like there was one guy working the bar and a bunch of tables. No pictures because it is very dark in there, but we had the fries and onion rings to start, which was a nice portion (these were ordered separately because the sandwiches do not come with anything). We tried the Huntsville Beef, which was def our favorite--melty cheese with nice flavors. The chicken sandwich and fish sandwich were ok but nothing exciting. Overall, we were underwhelmed and would not return given the number of great places to dine at in Middletown. read more

What a GEM honestly. I found this place by chance and I regret nothing. I've now gone here twice within two weeks time and I will likely be back. Surrounded by residential buildings, this old 1800s jailhouse brings NYC basement bar vibes to the Wesleyan neighborhood. I have yet to experience a bad cocktail here, and all of the food I've had has been delicious, high quality bar fare. read more

Harrie's Jailhouse - Cranberry mule and gingerbread manhattan - Sandwiches Near Me - Middletown, Connecticut

I've stopped by Harrie's 2 times and each time was great. The downstairs bar area is super cool! Each time the service was on time and friendly. The waiter took their time to explain the sandwiches during our first visit. The Big Butch burger was very good! The Harrie's sauce was even better!!! The 2nd visit I got the Folsom sandwich. The chicken cutlet was cooked to perfection (nice and thin) however the sandwich needed a sauce and a bit of salt. Lastly, the Devil Poppers are the BEST so they didn't make in the photos LOL. The poppers were so crispy I loved it. read more

Great sandwiches . Very friendly staff and cool atmosphere.Its a really nice place and I would highly recommend it! read more

Loved my experience here. I came for a wirk lunch and walked past the super cute outdoor area. It was too hot for us so we chose indoors which was in the "basement". Kinda darker but still cute and comfortable. Our server was the bartender and she was excellent. Friendly, knowledgeable of the menu and offered several great suggestions. I got the dip sampler as app and it was HUGE! Came with queso which was average and a pico de gallo that was fresh and flavorful. It included a French onion dip which was not so dip like to me. It felt like French onion soup and the broth was drained. Even tho it was different I still really enjoyed it on the warm pita and potato chips. The star of this platter was the pimento dip that I could not get enough of. It also included veggie sticks. Great app option. He got chicken bacon ranch sandwich w fries and really enjoyed. I got Folsom chicken which was pressed sandwich w a nice crispy cutlet. Perfectly thin and stacked together w pepper jack, that fresh pico and ranch. It was so good. Bread was crusty on outside and soft on inside. I got onion strands w my sandwich and they were delightful. We will definitely be back to try more and sit on the cute patio read more

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

See all

What a great first visit to Harrie's Jailhouse! Located inside an old jailhouse in Middletown and partially owned by the folks from NoRA Cupcake Co...I've had this place on our list since first hearing about it! We arrived around 6:30 on a Friday night and chose to sit outside. There was no wait and the hostess was so friendly! She even showed us the basement bar, where the old jail used to be. Very cool vibe! The outside seating is pretty small but really cute with fairy lights and high quality picnic tables. Definitely come for the cocktails! We had a hard time deciding but eventually settled on the El Warden (Ghost tequila, hibiscus, grapefruit) and the Thymes Up (gin, thyme, elderflower, lemon, Montenegro amaro) both were fabulous! For our second round we got the Jailhouse Fashion (their take on an Old Fashioned) and their summer mule which was a cucumber moscow mule! All incredible and definitely where you'll spend most of your money. Oops. For food, it's mostly handhelds and snacks - a great combo in my opinion. We had to try the Devil Poppers which were fried deviled eggs. Incredible. We easily could have eaten several trays. We'll be back for these alone! I opted for The Capone as my entree because it had fried mortadella - which was one of my favorites. The hubs got The Big Butch which was a massive burger that looked amazing! I was a little underwhelmed with my sandwich. I didn't realize it came on a hard roll either. I'm chalking it up to the fact that I hyped it up too much in my mind, because I have literally been excited to try this sandwich since I saw their first social post back in March 2021. It was a good sandwich, but I wasn't blown away like expected. We also ordered the Hot Potato appetizer with our meal which are buffalo fries made with their house buffalo sauce. EASILY could have drank a cup of that buffalo sauce...it was so good! All their sandwiches are ala carte so you need to pay for your sides - hence why we opted for the Hot Potato to share with our meals. Overall, great first visit and can't wait to come back with friends and to try more of their sandwiches. I'm looking at you next, Southern BLT! read more

Harrie's Jailhouse - El Warden + Thymes Up - Sandwiches Near Me - Middletown, Connecticut

This place is so cute!! Came here on Halloween weekend to check it out and they were having some fun events. We ended up sticking around for a few hours! The basement bar is a vibe brings me back to my college days. It's cozy and a great place to catch up with friends - you can also order their full menu there! It opens to the backyard where they have seating, heaters a fire pit and games. Beer selection is decent and the cocktails are great! Food is super casual Sandwiches mostly but fits with the theme of the place. Will definitely be back and bringing more friends read more

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

This place was a little bit hard to find and it was worth the search once I found it. It was fantastic. They have a really excellent menu and cocktails. I got the Cuban sandwich and it was perfect so was my mule cocktail. Our server was excellent, very friendly and attentive. read more

I thought the concept of this place being an old jail was so cool. My dad and I ordered chicken cutlet grinders for takeout one night. We were both extremely disappointed when we got home and saw how little chicken was in the grinders. It would've been a good sandwich if there was more on it. Unfortunately I can't say returning to this place to have a sit down meal is still at the top of my list read more

Harrie's Jailhouse - Chicken cutlet grinder - Sandwiches Near Me - Middletown, Connecticut

See all

Harry's does it again! This summer berry spritz is refreshingly delightful. You can taste the undertones of the lemongrass and blackberry. Hint of strawberry and the bubbles makes it the perfect summer cocktail and it's massive! read more

See all

Food was very tasty and generous portions. Some interesting combinations Cool ambience and good service

Great service and great food. A little tight for seating but overall we had a great experience! We will be back

A cool spot that made for a nice lunch on my way through CT. It's a basement bar that you access by walking on a gravel path to the back of the house in a suburban neighborhood. I enjoyed the southern BLT based on its many recommendations and it was delicsh but keep in mind that with the fried tomato and Texas toast it is a bit heavier than your average BLT, and the bacon doesn't stand out as much as a result. The fried onion strings were perfect and crispy. Overall a nice lunch with great service. I will keep this in mind for the future, definitely merits a return visit. read more

Best subs in Middletown! Best chicken cutlet, nice thin and crispy, but not too thin and also packs some great crunch and flavor read more

This place was okay. We ate outside and it took the waitress quite a while to get back and forth to our table from inside the restaurant. I'm not sure if I missed something but it seems very tiny inside and mostly a bar. Is also very dark and basement like. It's not a place I would be concerned about returning to for another visit. read more

It was our first time trying out Harrie's Jailhouse. I thought it was ok. I may give them another chance although I wasn't 100% satisfied. We ordered lemon chicken wings which indeed were jumbo and delicious. The chili was a little pricey for the bowl considering the take out container was only 3/4 full. For $11 I did think that was unacceptable. The cheesy bread that came with the chili was good. The chili was good. In addition we had the roast beef sandwich and onion strings which were good. I wasn't happy with the sweet potatoes; they were hard and spicy. I'm just used to sweet and soft sweet potatoes. I wouldn't order that again. read more

Went to Harrie's for lunch today, ordered a house salad with pulled chicken, which ended up being shredded/plain chicken. Not only was the chicken flavorless, but it tasted old....like DAYS old. When I told the waitress about this she informed us that food prep occurs on Wednesday's and that the chicken was prepared the day before. Which means, the chicken was not fresh AT ALL. The salad itself okay, balsamic dressing was pretty bland and basic. The waitress did remove the price for the chicken "add-on". Overall, I find this place to be under-whelming. The fact the food is not fresh, is a huge disappointment. Update: later that same day I had a pretty bad stomach bug and was VERY sick. Coincidence? I think not. read more

Wow. Just wow. After a fun Sunday afternoon of apple picking, the 5 of us were looking for some dinner: 2 adults, 2 teens (13 & 14) and a 10 yr old. This place got decent reviews and was close by so we decided to check it out. "Comfort food" sounded perfect. Upon arriving, parking was tight but the building was really cool. The restaurant is nestled in a residential area and built into the backyard and basement of an old 3 story brick house. The patio is around back for outdoor seating which we initially thought we would want but the hostess let us know they had a large party coming. They had one table for us outside, but I appreciated the heads up on the expected crowd, and we opted to go inside. Inside is literally a basement bar. It's not huge, but it's not crowded either. We were seated right away. There was one, really LOUD guy at the bar cursing and dropping f-bombs which was not cool. My 14 yr old asked if we could go back to the outside table to get away from him, but as a couple more families filed in either someone asked him to tone it down or he left- I don't know which but we didn't have to hear his mouth anymore which was fantastic. The menu was fun and interesting. The specialty cocktails were unique. The food options were different but familiar. The bartender doubled as our waitress which made me a little skeptical at first, but service was great. You would never have known that she was double-hatting. She was super friendly and happy, took our orders quickly and the food was delivered quickly. This is where the experience turns from good to amazing. The food. Oh my goodness- THE FOOD was out of this world! Served on a tin tray with imitation newspaper, it's not fancy looking but the flavors were incredible. While my little guy enjoyed the homemade Chex mix, the older 2 shared the lemon pepper wings as an app. They were visibly crispy but not greasy, layered in seasoning and lean. I don't know what kind of chicken they use but there was no fat between the skin and the meat. They were so good we ordered 2 more to go to take home with us. They were THAT good. Then the meals came, serves on similar but larger tin trays. My son's "chicken tenders and fries" was an actual chicken cutlet, freshly breaded and cut into pieces. It was NOT the usual pre-fab, probably frozen junk you get at most restaurants. This was a hand-needed cutlet you would see in a dish like chicken park. It was big and enough for 2 meals, but priced for one. We brought half of it home. The older boys ordered a Philly cheese steak and a cheese burger and fries. Both raves about their sandwiches and the fries were gone within minutes. Although the food looked averaged sized on the big metal tray- it was an illusion. Neither of these insatiable boys could finish (despite their talk of how hungry they were.). We brought home half of each. I don't know what my husband ordered but there was nothing but crumbs left on the plate (and he's a pretty big guy.) I ordered a salad with buffalo pulled chicken on it. Holy cow- I didn't realize how big that salad was. Again, the optical illusion of the gray is misleading but the flavors I'm the salad popped but married together nicely. The pickled jalepeños were unique and fresh- adding some kick. The pulled chicken just melted in my mouth with the zing of the buffalo sauce and creaminess of the blue cheese dressing. I was full about halfway through but couldn't stop eating it. All the produce was fresh and crispy- the dressing was oddly light but flavorful. I seldom rave about a salad (and to be honest- I thought I was ordering a "chicken salad" sandwich that just had a lot of veggies on it ) but this sucker was epic. In the end, we had a great service, phenomenal food at reasonable prices and left with full bellies plus enough leftovers for the kids to have a second meal. read more

I came here for the first time yesterday. If my friend hadn't already been here before, I would have been lost. The location is odd and I think they could have better signage. After learning about the history of the building and settling in the basement, I quickly ordered the El Warden cocktail. I personally enjoy spicy cocktails so this one was a winner! I ended up having 3 rounds throughout the night. Choosing food was a little difficult because everything sounded really good. Eventually I decided to get the Dip Set (not pictured) for the table and each dip was satisfying. For my entree, I chose the Sanguiche (minus the ham) and it was yummy and huge! I also ordered fries on the side that were pretty basic...some Harrie's Sauce helped for flavor. Considering the price of the sandwich, I think a side should be included. Overall, I'll be back again to try other food options and sip some more cocktails. read more

Harrie's Jailhouse - El Warden and Watermelon Margarita - Sandwiches Near Me - Middletown, Connecticut

See all

Wow. Wow. Wow! Everyplace I gather info, Harrie's is the place to try! My fellow Yelpers, social media, and CT Magazine all seem to be in line. Went for lunch today and was knocked out. Henry handled the place by himself and he was awesome. The atmosphere is cool. The food, outstanding. The Huntsville Beef and the Sanguich were both worth ordering again. We added Fries and Onion Strands. Also both excellent! Feels like a frequent stop in our future! read more

Cocktails and food were delicious. The service was phenomenal!!! We were in the basement looking forward to see the rest of the restaurant.

Came here for an early dinner 2 weeks ago based on the good reviews, table of 6 very disappointed. our waitress was very nice and the only reason this is a 3 star and not 2 star review. we had 2 orders of mac and cheese one came out cold and soupy . my chicken sandwich was ok at best . my daughters burger was mediocre at best my son got a southern BLT that was very good . out of 6 people at the table only 2 were happy with what they ate. wouldnt come here again. read more

horrible meal . burger was disgusting . meat was rancid tasting . fries were the only reason the one star . I had fire poo all night

Out for an early dinner to take advantage of the sun - sat on the patio without needing heaters. Started with the dip appetizer - would rate it a 3.5 out of 5. The black bean hummus had great flavor but the consistency wasn't hummus - it was thinner, more like a sauce that was hard to leverage with the sides of veggies, pitas and potato chips. The chili queso was good but should have come out hotter - the whipped feta was our favorite- never had whipped feta before but now I will do something like it at home - great concept! When multiple people are sharing a dip platter, it would be great to provide a serving spoon, etc. Next course, hubby and I shared the autumn turkey sandwich spec - really enjoyed this and appreciate them plating separately without us having to ask. Sandwiches are hearty so sharing one worked for us after the appetizer with no additional sides this time. If you are in the market for sides, can vouch for the fries based on previous visits even though I never posted photos. service was friendly and prompt ! read more

See all

I'm in love with this speak easy type atmosphere! Love the history of the building (I'm a sucker for buildings with a story) We walked in the top part of the building and was quickly advised we most likely want to be in the basement. All was not lost though. We got a personal mini tour of the building as we were lead to the basement/bar area. We ordered the chili cheese fries. Which were perfect! They do not salt their foods so if you are a salt lover you may want to ask for it on the side. We also got the fried deviled eggs ... they really did something with that! Those are hands down the best thing on the menu! We also split philly cheese sandwich which was underwhelming especially for the price. No flavor just meat,cheese and bread. The sandwiches don't come with any sides but they are very large. The staff was wonderful. Our waitress even made me a fresh lemonade which I thought was so nice of her. It's worth the experience. read more

See all