Such a great towny bar. Adrian is amazing bartender who remembered our names and our drinks after just one visit. She is always cheerful and friendly. Food is surprisingly good. I definitely thought it wouldn't be so delish just because it's a town bar. Boy was I wrong!!! You need to try the burgers. They are out of this world!! read more

After so many years coming here, it still never disappoints! The food is still excellent especially their buffalo wings and burgers. However I have to give a high praise for their chili, so good I left the bowl clean . The service is still excellent and they really take good care of you. We enjoyed the music playing on the box and we still love the decor inside, that's what makes the place fun. Very fair prices, great drink options and a good time is always happening. So long as The Winchester is around, I will always come here whenever I visit. read more

Winchester Cafe - House Chili - American Near Me - Portland, Connecticut

Stopped in here to get drinks, and had a great time. Bartenders are friendly and quick. The vibe is super cozy, divey biker bar (in a good way!) I loved it here. Can't wait to go back! read more

unless you are a "regular" don't bother. Unresponsive and rude bartenders, mediocre food. Strike 3. sorry June, sadly I won't return... I believe you and a multitude of others watched me sit patiently, then gently request service a multitude of times before being snapped at and having the menu grabbed out of my hands after trying to smile and politely order... read more

My wife and I stopped in for a lunch with our daughter and her husband. Everyone got something different. Our wait staff (god bless her) was clearly on drugs,so sad. The food was pretty bad. I am not looking to rip a place but even if you're five sheets to the wind this food would still taste lousy. Thats about it.. read more

My burger was very dry. I asked my waitress for crispy fries. She brought out what looked like what's left in the bottom of the fryer. It's a place for locals but they were very loud and stared a lot. read more

Came solo looking for a place I could relax and have a beer with locals. Yea this was it! They had musician Steve McGrath playing he was amazing. I got their signature Winchester burger and it was perfect. Chilled here for a couple hours a couple beers and it just feels like home. read more

See all

The owner of this bar is one of the rudest human beings I've ever encountered. My boyfriend and I were having fun dancing and she asked us to stop. I've never gone out at night being told to not dance with my significant other based on someone being so wretched. If you go enjoy her misery. 0 stars read more

Cute place with nice outside patio. Inside is super cozy snd cute too. Food was good for a casual place like this. We had burgers and a pulled pork sandwich. Service was good and friendly. read more

Winchester Cafe - Patio - American Near Me - Portland, Connecticut

See all

A unique cafe-bar on the 66 CT. When it's real dark and cold, the lights of this cafe looks like big M sign. Food and drink are not far! One time we were driving from Massachusetts very late, couldn't find any place open, and we saw the lights! When we went in, it was so warm inside, music was live, people were standing all over in this tiny cafe! It was heaven for us. Last Saturday, I went there with my son. It was karaoke night. We had a few beer while we're waiting for karaoke to start. My son like the juke box behind our seats. He put few coins and others too. Around 8:30, someone started to sing. It was bad. almost everyone who sang were extremely bad. But it was fun to watch people singing without hesitations. read more

Winchester Cafe - Winchester cafe - American Near Me - Portland, Connecticut

See all

We love this place! It's a cool relaxed vibe inside - it's like stepping into an old country bar. The bartenders hustle and even when it's busy we always have great service. The food is really good - especially the bbq. They have a nice patio on the side and they allow dogs out there too. They always come out with a bowl of ice water for our pups. Great biker stop too - would highly recommend! read more

Went out and enjoyed a Bacon, Mushroom/Sour cream burger (A Winchester original)! Mmmmm! It hit the spot with a nice cold tap beer. This spot is a local landmark! Donna (the owner, has really made this place a delightful and fun destination that serves a dedicated local crowd and impresses all travelers who stop in! read more

A great dive cafe that really brings that unique country side bar in the woods. Decent amount of beer on tap, and a nice local bar to support. It's a nice place for drinks, happy hour and food. Live band also makes it a plus. read more

Winchester Cafe - Potty jokes always make fir good menu - American Near Me - Portland, Connecticut

See all

First, Linda is awesome! She was kind, prompt, attentive and pleasant; I'd be disappointed to find anyone at the bar when I return! Secondly, the food: oh.my.god. We had the chili; fantastic! Hearty and delicious. Not spicy. We also had the BBQ Beef sandwich and patty melt. The beef literally melts in your mouth. Smoked perfectly, tender and full flavored, you can't go wrong if looking for a BBQ delight. The patty melt was extraordinary; one of the BEST burgers to ever cross the threshold of my lips. The cheese was a gooey and delicious complement; not overwhelming by any means. The buttery, crispy, golden bread held everything together perfectly. As far as the drinks were concerned, they are delicious and generous. Loved my Bloody Mary & screw driver. He had beer on tap and was without complaint. The decor is fun and fascinating. From silly comical signs to the old fashioned chandelier and telephone there are elements to this place that make the experience fun and homey! I highly recommend stopping here for a bite and a brew if you happen by. read more

Winchester Cafe - Patty Melt & Fries - American Near Me - Portland, Connecticut

See all

Worst service I have ever had. I ordered a sliced prime rib sandwich and they literally took a gray, fatty huge slice of a steak on a roll. Who orders a huge piece of prime rib and slaps it between 2 buns. When I told them this wasn't what I ordered, they refused to acknowledge it and doubled down charging for food I did not touch. read more

Wow. This was unexpected. A bunch of us gals headed into this place after my friend's baby shower. I know.....we're savages. Any way, we got some looks when we walked in but the mood changed for the better. We got some brews and listening to the Tom Petty cover band that they had there. It was a great bar. The bathroom was also impressive because it was clean and roomy. And the patrons were so friendly to us. I would totally go back to this bar. Thanks Winchester!!!! read more

We were very disappointed based on the reviews we saw here. The bartender was also responsible for the tables and seemed to be the only person working (on a Saturday night). I don't blame her at all for things taking a long time, she was nice but definitely busy. We both ordered burgers, and I asked for mine with onion rings which it did not come out with. The fries it came with instead were very undercooked. I didn't say anything about the mistake because she seemed very busy, and I've been in her shoes, I get it. Our burgers were flavorless and we both only ate half. When she finally came with the check I was still charged for the onion rings. I told her and she made the change in price which I appreciate. The food was so disappointing however that we probably won't me back. read more

What could have been an enjoyable experience was ruined by the nasty bartender who felt it necessary to point out that she felt under tipped. Too bad because we had a great time here on several occasions with good food and good friends The owner is nice-too bad her Saturday night bartender is unfriendly and downright RUDE. read more

Term "cafe" is misleading in their name. We were expecting a bar/grill type place with good burgers and their "award winning chili" as was advertised. We were pretty much in the middle of who knows where in the "backwoods" of Connecticut and just looking for a place to eat before driving down to watch a play in East Haddam. Yeah... replace "cafe" with "Dive Bar." I am ALL ABOUT the dive bars, but not when I'm starving and want food! Everything was just pre-fab, throw in fryer and cook, and serve on plastic (PLASTIC!) plates. And um... no real service to speak of. I liked the jukebox I could play country at, the local townies that all knew each other, but the food and "service" was HORRIBLE. Which is... what you should expect at a dive bar. Shame on us for expecting any kind of real food at this place. But I guess... I was hoping for a diamond in the rough. :) read more

So I am updating my review since my dad's band has had several more gigs here and apparently the singer told the owner about the issues. Since then, I have had nothing but an enjoyable experience here. I was surprised by how delicious the food was!! The Philly cheesesteak wrap is amazing. So is the crispy chicken ranch wrap. I also love their Quesedillas. Sandy the bar tender is really sweet and helpful. The bar service is still slower to non locals, and one time I asked for a glass of tap water before I went on and sang with the band and had to pay for a bottle "because there was a band". A few minutes later I saw a local with a glass of water. Still would call it a dive bar, but the food is worth checking out! read more

We stopped here on the way from NYC to Maine. It's a very quant place with a bunch of antiques, old posters, lighting fixtures and cool signs like: this is not the Burger King, you don't get it your way, you get it my way or you get no dam thing. Don't worry, the place is super friendly, very accommodating, delicious and no frills food and amazingly warm service. They have outdoor seating n the tables inside are so country style fab, it's a shame I didn't take more pics. The place reminds me of an old west saloon with all the cowboy n Indians memorabilia. read more

Eclectic atmosphere. Definitely something to keep the conversation going. The weekly specials egg rolls are delicious and interesting! Regulars seem to prefer the bar although there are a few tables as well. It is a bit dark and dated, but cozy at the same time. I wasn't impressed by the menu, but it has some solid munchies and burgers. read more

The food is horrible.... The chicken wings tasted like they were coated in cigarette ashes and the burgers were burnt and fries were cold. The karaoke entertainment is entertaining when all the locals get drunk and become Elvis for the night. But the place is a dive read more

Went here a couple Saturday's ago and it was PACKED with bikers. Really cool vibe. I was surprised how much food they had on the menu. Best ham and grilled cheese I've ever had! And the bartender was super attentive and nice. Definitely recommend if you're in the mood for awesome weekend food and drinks read more

First time here . Have driven by many times... Wish we had stopped sooner! Sandy the bartender was awesome ...guided us through the menu specials . Just had the philly cheese steak egg rolls with Gorgonzola spicy dip...... Awesome !!!!!! So good had to order a second batch along with a salad with that awesome Gorgonzola dressing!!!!! Husband had the chicken sandwich on a biscuit with bacon and cheddar cheese....over the top!!!!!! Well worth the stop!!!!!!! read more

Very rude bar tender. Flat soda and the prises are out of control. The beer is warm. At least the band kicked ass.

Husband and I love this place. We try to make it as a pit stop when we ride. Sitting at bar you get great service. Food is very good for a bar. There are bikers there but we don't bite...much. Brought young son there and he was a bit taken aback by all the bikers, but when he loudly announced that he was a "biker" ( on his mountain bike) he got a lot of laughs and a high five from one of the surly biker guys! We always had a good meal there and met some good people. read more

I disagree that this is a "dive" cafe. I think it's what the bar at Ft. Wilderness in Disney World ought to look like. Authentic (looking??) Winchester rifles hanging over the bar. Rustic in a nice way. Food was better than Disney but that is damning with faint praise. The french Fries were inedible. The side salad was fresh, but the vinaigrette came from a jar. The Buffalo Burger was fine. Not inspired, but OK. Next time its down the street to Farrels read more

I've been stopping in here for 20 years now.the food is good and the beer is cold. Sandy the bartender is really nice.a nice place to stop when your out riding around. read more

I read the previous post and the girl doesn't say what she ordered or what time she was there but everytime we stop in "The Winny" the food is good, the burgers are awesome, and they even have Bison (Buffalo)burgers. Their chili is very good ,the beer is cold and the service is always the best. Maybe the fist reviewer ordered fried food and she got what she ordered. read more

Stopped by on a weekend drive. Excellent service and dog friendly staff on the patio. The food was solid American grub, good with a cold beer on a hot day. Waitstaff was awesome. read more

This isn't a biker bar, its just a bar, that some bikers frequent because its a diner on 66 which is a great strip to cruise down. Anyway, great burgers and beer cool atmosphere. read more