You know those places that just feel like home the second you kick the slush off your boots? That's the vibe at Jimmy O'Connor's Windham Mountain Inn. In a world where corporate resorts are turning everything into a "luxury experience" with $20 artisanal water, this place is a defiant, wood-paneled middle finger to all that pretense. It’s an authentic Irish pub and inn that hasn't lost its soul, even as the mountain across the street transforms into a semi-private club with six-figure initiation fees.
If you’ve spent any time in Windham, New York, you know the green sign. You’ve probably seen the cars packed into the lot on a Friday night. But there’s a lot more to this spot than just a place to crash after skiing. It's a piece of living history.
What Really Happened with Jimmy O'Connor’s Windham Mountain Inn
Let’s clear the air on something first. People often get confused about who "Jimmy" was and whether the place is still the same. James P. O'Connor, the man who started it all, passed away back in 2017. He was a first-generation Irish American who basically built this place on grit and hospitality. He and his wife Mary ran it for nearly 50 years.
Honestly, the community took it hard when he died. Jimmy wasn't just a business owner; he was the guy who helped every Irish immigrant find their footing in the Catskills. He was a Fairfield grad with a Jersey City heart. Today, the family legacy continues through his son, John. If you walk in and see a guy who looks like he knows everyone’s name—that’s likely John. He’s kept the "no-nonsense" spirit alive while the rest of the town goes upscale.
Why people keep coming back
- The Burgers: People talk about the "Jimmy O’s Burger" like it’s a religious relic. It’s not fancy. It’s just a massive, juicy burger that hits the spot when you're starving.
- The Price Point: In 2026, finding a room in a ski town for under $200 is basically a miracle. You can often snag a room here on a Sunday or weekday for around $146.
- Zero Pretense: The rooms are clean, but let's be real—they're "retro." Think carpeted floors and wood paneling. It feels like your cool uncle’s basement in 1985, and that’s exactly why people love it.
The "Anti-Club" Energy
Right now, Windham is going through a massive identity crisis. The main ski area rebranded as the Windham Mountain Club. They’re focusing on "elevated" dining and exclusive memberships. It’s making a lot of locals nervous.
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In the middle of all this change, Jimmy O'Connor's Windham Mountain Inn stands as the anchor. It’s located at 141 South Street, literally across from the golf course. While the mountain is talking about "Italian Alps-style concepts," Jimmy’s is still serving Murphy’s Irish Stout and steak dinners with "Jimmy Fries."
It’s the kind of place where you can actually afford to bring your kids. They’ve got a pool table, a jukebox, and even an arcade area. It’s loud. It’s friendly. It’s exactly what a mountain town needs when the developers start moving in.
A Quick Reality Check on the Rooms
Look, if you’re looking for a spa and a pillow menu, go somewhere else. I’m being serious. The rooms at Jimmy’s are simple. They’ve got:
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- Solid Wi-Fi (essential for 2026).
- Microwaves and fridges (perfect for leftover pizza).
- Immaculate beds (the reviews don't lie about the cleanliness).
The trade-off is that you might find the decor a bit dated. But when you’re three minutes from the lift and you’ve saved $300 on your stay, you won't care about the wallpaper.
The Community Hub Nobody Talks About
Most travel blogs just talk about the skiing. They miss the fact that Jimmy O'Connor's is the heartbeat of the local Irish community in the Catskills. For decades, this was the spot for the AOH (Ancient Order of Hibernians) and anyone with a drop of Irish blood.
There’s a reason it’s listed for sale every now and then—running a legendary inn for 50 years is exhausting. But every time the "For Sale" signs pop up, the community holds its breath. We’ve seen enough "mini-resorts" take over. We don't need another one. We need the pub.
What to expect if you go this season
If you’re planning a trip, keep these things in mind. The check-in is usually at the bar. Yes, the bar. It’s efficient. You walk in, grab your key, maybe grab a pint of Guinness while you're at it.
The service is "stand-up guy" service. They aren't going to grovel, but they will make sure your room is warm and your food is hot. If you have an issue with your booking, talk to John. He’s known for being a straight shooter.
Actionable Insights for Your Visit
If you want the best experience at Jimmy O'Connor's, don't just show up and expect a Hilton. Follow these steps to actually enjoy the local flavor:
- Book via Phone: While they are moving toward online reservations, calling them directly (518-734-4270) is still the best way to ensure you get exactly what you need, especially if you have a big group.
- Sunday Stays: This is the pro tip. The rates drop significantly on Sunday nights. Most of the weekend warriors head back to the city, and the pub gets a bit quieter, which is when the real storytelling happens.
- Skip the Fancy Breakfast: Most rooms have a fridge and microwave. Grab some breakfast burritos from a local spot or stock up at the store. Save your appetite for dinner at the pub.
- The Steak Dinner: Everyone raves about the burger, but the steak dinner with salad and fries is the sleeper hit on the menu. It's old-school portions for a fair price.
- Respect the Vibe: This is a family-owned, local institution. Be cool to the staff. They’ve been through a lot of changes in Windham lately, and a little kindness goes a long way.
To truly experience Windham without the corporate gloss, you have to spend a night here. It’s the last of a dying breed. Grab a seat by the fire, order a round for the table, and appreciate the fact that places like this still exist.
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Check the current room availability by calling the inn directly or visiting their official site at windhaminn.com before the peak ski weekends hit.