Jimmy O’Connor’s Windham Mtn. Inn

Look, this is a little strip of rooms behind a local bar. We found it to be as described. Old school room but it was clean and everything worked. The bar/restaurant was a casual environment with friendly staff. My son and I had burgers and they were good. For a fast trip we would consider staying again.

Popped in for some beers and some dinner after a weekend of work in the area. We immediately fell in love with the cozy, classic charm. Glowing lights, a fireplace, jukebox and piano; all the sweetest touches you don’t find in places anymore these days. The owner stopped by our table and was an absolute gem, just radiating welcoming energy. Beautiful evening, we will return for sure!

Great, atmospheric spot! The steak was amazing 🥩 — super juicy and cooked perfectly. The whole vibe is cozy, clean, and really welcoming. I stayed here overnight before riding at Hunter Mountain — perfect place to rest up and head out early in the morning. Special shoutout to the owner, John — not only a genuinely great guy, but also one of the strongest street snowboarders of his time. ( The latest one according to Denis Bonus 😅) Highly recommend!

Absolutely awful experience. Went there for dinner and drinks with my college friends (one of them being a regular). Got told they weren’t serving food at 6:30 pm on a Monday? Numerous other parties were actively being served food/waiting on food and the table next to us ordered 5 minutes prior to us getting there. We left right away, I can also say they lost a regular and none of us are ever going there again.

We went to the bar for drinks and dinner on a quiet Monday evening and was met with the most genuine and authentic hospitality by John. This is the Windham experience we have been searching for since having our 2nd home here in 2020. The area changed so much after Covid. But John and Jimmy O’Connor’s reminded us that there are still family run businesses who have been here for a long time and who built the community and culture here. We need to support them more!!!