Where "Old School" is the Only School Jimmy O'Connor's isn't trying to be a trendy gastropub; it's a family-owned authentic Irish bar that has been a Windham staple for over 50 years. It's the kind of place where the floorboards have stories and the Guinness is poured with the respect it deserves. One of the coolest things about Jimmy's is the family legacy. The bar is a pillar of the local community, and if you're a fan of snowboarding, you've likely heard of John (Johnny) O'Connor. John grew up right here in Windham and went on to become a famous professional snowboarder (riding for brands like CAPiTA). His roots in the mountain culture are baked into the atmosphere of the pub, making it a "must-visit" for anyone who respects East Coast riding history. The Burgers: While the menu covers all the pub classics, the Jimmy O's Burger is the go-to. It's a no-nonsense, juicy mountain burger that hits the spot after a day of freezing temperatures. Pair it with a basket of "Jimmy Fries" and a pint of Murphy's Irish Stout. The Vibe: It feels like a true public house. You'll find a mix of muddy hiking boots, snow pants, and local regulars all sharing the same space. Entertainment: Jukebox & Felt The back of the pub is where the real fun happens: The Pool Table: It's almost always in use, serving as the center of gravity for the room. The Jukebox: It provides the perfect soundtrack to a night of "just one more drink." Whether it's classic rock or Irish folk, the music keeps the energy high without drowning out the conversation. Note: Just a heads-up that Jimmy O'Connor's was recently listed for sale to find its "next chapter" after 50 years of family ownership, so now is the perfect time to visit and experience its classic legacy! read more

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Excellent Irish pub with amazing burgers and a chill vibe. The family owned restaurant is my favorite spot in Windham for a burger and a beer. The Murphy's stout is delicious and similar to a Guinness. Highly recommend! read more

Jimmy O'Connor's Windham Mountain - Best burger in the Catskills - Irish Pub Near Me - Windham, New York

My friend and I were huge fans of this place when we stayed two nights (and had dinner one evening). Background story: we booked another place called Hammo's via Airbnb (and they confirmed our reservation). We picked that place because it advertises itself as dog friendly. We drove 2.5 hours from NYC to find that Hammo's was completely deserted! Asked the restaurant next to Hammo's what's going on, to find that Hammo's has been closed for months, and there were zero visitors. We looked around for a place while I was on hold with Airbnb for 50 minutes. Someone in the neighborhood recommended Jimmy O'Connor's as a possible dog friendly accommodation. My friend asked the friendly owners, and while they aren't normally pet friendly, they were completely compassionate and sympathetic to our situation and let us stay there (and thankfully, my dog is very well-behaved, so I felt confident that she wouldn't leave any damages). They were completely understanding of the fact that I didn't want to kennel her in a place or people that I didn't know. The room had everything we needed: two double beds, a refrigerator, air conditioning, TV, clean shower. Absolutely no complaints about the room. It was also cleaned well while we were out. We asked for late check out, and while they couldn't guarantee it immediately, they worked something out for us and got back to us ASAP. The stay was absolutely wonderful and I would recommend this to anyone! It's also a short drive to a street with several restaurant options. Speaking of restaurants, we ate at the bar outside (since no indoor right now). The burger was delicious! Service was also excellent - the lady running the show was checking on us and was so, so nice. They also have a fire pit. read more

Jimmy O'Connor's Windham Mountain - Burgers and beer (plus doggo) - Irish Pub Near Me - Windham, New York

Delicious burgers, juicy and flavorful. Friendly service at the bar. Old Irish pub decor, lots of family photos and items from the Emerald Isle. Bring quarters to play pool or Galaga/Pacman. read more

I absolutely love this establishment. Jimmy O's is a traditional pub and eatery. Cold beer and delicious burgers, a glass of wine and a steak dinner, Irish coffee and a newspaper; whatever your mood calls for, Jimmy O's can deliver. But, Jimmy O'Connor's is more than just a good beverage and a wonderful meal. Jimmy's is the kind of bar our grandfathers used to drink at (if they were Irish). And I mean that in a good way. Profanity is not tolerated, nor are "wife beater" tee's. The classic juke box, the day's newspaper, the pool table and various arcade games are all mainstays. On cooler evenings, the fireplace is lit, creating an ambience unlike anywhere else on the mountain top. Regardless of the occasion, or even if there is no occasion, Jimmy O's is my favorite place to grab a drink or a meal, alone or with friends and family. read more

This was my first time here, but it felt like home! Such an authentic and cozy pub with a pool table, fireplace and even a Christmas tree with family ornaments on it. The epitome of your local dive bar and 1 minute away from the mountain. Definitely will be coming back! read more

Great place to stay for a night or long weekend. Food and accomodations were excellent! I highly recommend staying here next time you take a trip to Windham. read more

Atmosphere: Good, Irish Pub / Dive Bar vibe Burger: excellent Bartender: Not Good. If the group I was with was not in the bar, the place would have been empty. I think she was annoyed we came in the place. read more

I've been coming to Jimmy O'Connors for just over a decade and always enjoyed all aspects. The rooms are very comfortable and always clean. The staff is incredibly friendly and helpful. The bar is a fantastic place to hang out with a terrific burger, drink options, and a pool table. Conveniently located just minutes from the mountain, this cozy gem in the mountains is my number one spot when visiting Windham. read more

Jimmy O'Connor's Windham Mountain Inn! W00t! Oh boy, what a hoot. Bar is a local watering hole / juke joint. Down-home flavor and local custom. Dance floor and pool table, simple gastropub menu, and a sign declaring "No Russian vodkas served here." What's not to love? Inn consists of about half a dozen rooms in a separate building out back. Pros: Affordable, well-heated, clean, and only about 1/4 mile from mountain. Cons: Paper-thin walls, tiny restroom with no vent/fan. read more

Jimmy O'Connor's Windham Mountain - View from South Street - Irish Pub Near Me - Windham, New York

Delicious steak, fries and and salad dinner. The steak was made perfectly and was New York strip. The service was good and friendly. Enjoyed the beer on tap and the pool table as well. It was a very cozy, old fashioned atmosphere. read more

Nothing fancy, everything good. Classic, just what you need after a long day of skiing.

Dank smelly bar. Nasty bar maid from Ireland. Good Murphy's Stout. Had the burger which was served on the thinnest cheapest paper plate: essentially a thick napkin. If they are cutting corners on paper plates---what are they cutting corners on in the kitchen? If you want a good burger go to Zacks place. read more

Very disappointed, room smelled badly "old musty smell" sheets and towels also smelled they were not freshly laundered, for $150.00 i would expect better, bad experience i would not recommend. read more

I just came back from a weekend at Windham and a friend and I stayed here. Considering it was a last minute trip and it's a long holiday weekend, it was the least expensive place with a room available and it's only literally 2 minutes from the mountain... they're on the same road. You can see the ski slope from outside your hotel room. The bar was also the front desk, so we had no problem checking in at 12:30 in the morning. it's a quaint little bar with some really interesting covers of songs. We heard an acoustic version of "Livin' on a Prayer" but it was so slow. It was an ok bar with cheap-ass food and drinks. No 4 or 5 star rating because like the previous review, the walls really are paper thin. We could hear our neighbors coming back from the bar and moving around their room. The shower spray was painful... you know how workers spray the graffiti-ed walls with the water hose? Yeah, that was our shower head. And the water got cold real fast. And the jukebox didn't work in the bar... i lost 25 cents trying to put in a song. That was 25 cents i could have used for the tolls getting home. read more

We always look for local spots when we come into town. Talk about not being welcomed. The waitress completely forgot to place our order which was fine because we were having drinks. We ordered a few rounds and one of beers that the waitress put down partially spilt but I caught it so it wouldn't completely fall over. The waitress didn't apologize for that beer spilling all over my friends pants and she didn't bother removing the half spilt beer off the bill. She than took the bill back and added even more tax which came out of nowhere. As we were getting ready to leave, she said "Happy New Year" and before we could even say anything back, she goes "yeah me too." The food is simple but good. I definitely won't go back because of that waitress alone. I wasn't going to even write a review but that was an appalling experience. Maybe that waitress had something personal going on. We didn't even want to ask her questions because we were met with a cold and negative attitude every single time. Dive bars are usually the way to go but this was something else. read more

1 hour wait, menu was poor. Food was horrible. Cook actually showed up with a bag of cheat like 1 hour after opening.

Go here and order the hamburger right now. Seriously, stop what your doing and go there now. And the chicken wings. He grinds fresh beef himself, that day as far as I can tell. amazing flavor and simplicity. If you have ever been camping or on a long hike then you may know how amazing a burger tastes after that long day when you cook it outside over a campfire you just made. No frills, just simple taste of meat smoked lightly with that campfire taste. Thats exactly what you get here. It's just perfect. The bar its self is a local joint with nice people, old arcade games and a pool table. You don't see the kitchen or anything, you just see two hands pop out from behind the door with your food behind the bar and then the bartender brings it to you. Theres a hotel attached apparently but i was to drunk and obsessed with my burger to notice. read more

Worst waitress/bartender. No people skills. Mean nasty rude. Went in party of 5 ordered drinks. No drinks, food only we were told. We looked around, no one had food on their table. We wanted to order food also but the nasty attitude left us feeling we needed to get out of there. As we left we asked 2 tables we walked past that had drinks on the table if they ordered food, both said no. We went to The Tap House on Main Street had food, cocktails and a great time and spent a couple hundred dollars. read more

Good Irish pub. Quiet with a friendly crowd and staff. Best burgers in town, hands down. Pool table is a plus.

This was just a place to sleep, but there is a bonus. There is a bar just outside our door and we could drink the night before skiing and have fun with darts and bar games, the juke box was pumping. Stumble back to the room and wake up the next morning. Had the bunk bed room, which was fine for the three of us. Just a place to lay down and rest. Price was cheap, even during ski season and you can drive right up to the room. read more

Just finished a grueling 2 day hike and all we wanted were burgers and fries. This place met and exceeded those needs. It was the only place in the area open at 10:30 at night, and the staff were super friendly and accommodating given the social distancing situation. We left feeling very satisfied. read more

Hands down best burger. We come to Windham for weekend getaways from our home in NYC and I'd take this burger over the famous burgers at Corner Bistro and Minetta Tavern any day! read more

Jimmy O'Connor's Windham Mountain - Heaven - Irish Pub Near Me - Windham, New York

Definitely NOT the best burger in Windham and not even honorable mention. I had no expectations of this frequently visited local standby with respect to service, ambience, and price. Bottom line is the food is pretty pedestrian. The burgers were mealy and tasteless. The wings were crispy and tasty but batter fried always makes everything taste better. If your looking for a reliable watering hole then belly up to the bar. Otherwise I'd would pass for a better "best burger" alternative. read more

I thought I was getting a good deal but you get what you pay for. Staff is super sweet but rooms need serious updating. Bathroom is tiny with one little sink with a little mirror squeezed above it and that is the ONLY mirror in the entire room. We came up for Thanksgiving and the only place to eat here is closed! On Weds it did not serve ford till five and we arrived at 1pm in a snowstorm :( No little store for bottled water or ANYTHING and it is owned by the Windham mt. Could and should be much better. feels like the 80s read more

When calling to book the room, I dealt with the rudest man in recorded history. He ask me where I am driving from. I told him New York. His reply "I'm in New York, where in New York". I told him New York City. His response, "Where in New York City, Queens, Brooklyn . . . " I cut him off and answered "Manhattan". He then told me that Manhattan was the last place that he would have thought of when I said New York. The guy was the epitome of obnoxious. If it weren't for his establishment having the only available reservation in the entire town, I would have let him have it. Please book in advance so that you can avoid this uncivilized human being. read more

Local dive bar with great burgers. Friendly staff and clients. Good stop for skiers looking for a few beers! Bar tender is hilarious

Average roadside bar with equally average bar food. I heard the burger was the thing to order. Ordered a buger and fries. The burger was on the small side more like a slider and average at best. Service on a paper plate without utensils was in keepig with the ambience. read more

Decent small hotel. Jimmy is friendly, as is the bar staff. We had a great time. Our room slept four very comfortably. Good value.

Went in last Friday and the owner couldn't have been more rude. My buddy asked for coffee and he said, "I'm not making a pot for you." This was at 11 pm on a Friday in a nearly empty bar and we were a group of 5. I asked for Bushmills and he was very insulting about Northern Ireland not really being Irish and said he only carries Irish Whiskey. He was totally ignorant and boorish. The woman behind the bar was embarassed and tried hard to make us feel welcome. We left soon after and went to The Cave in town. read more

Hidden gem. Love this place! Absolutely beautiful scenery with cozy accommodations couldn't be more pleased with my stay here.

O'Connor's Windham Mtn. Inn is a great place, warm, friendly, and inviting. Sure the rooms aren't what you would get in Manhattan(at three times the price), but you are in the Northern Catskills for God's sake(in God's country!) Though the menu is somewhat limited, everything on it is excellent and deserving of five stars! You will not get a better steak or burger anywhere, and their prices are fair. Jimmy and staff are legends, I go there all the time from NJ. read more

Fantastic place! For 13 years in the Fall I have spent the weekend in the Motel, inexpensive and everything you need for $80 especially after visiting the Bar/Rest 50 yards across the lawn and then wake up and it the golf course. Thanks for all the good times . mm read more

This place has been a fixture for decades. The rooms are simple, set up for families, bunk beds and all, are well ventilated with windows that open, and stay cool even in hot weather. The retro pink and black tile bathroom brings back memories and they welcomed my dogs who enjoyed sitting out on the large lawn set back well from the road. Simple lawn chairs set up outside give an unobstructed view of the mountains to the east. Not for the pretentious, which sadly Windham has become. Down to earth, great hamburgers and Irish all the way. So go pay double or triple the price for air conditioning and antiques. You wouldn't fit in here with the great people who come to the bar and restaurant. read more