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    The Tipp Tavern

    3.1 (20 reviews)
    Open 12:00 pm - 12:00 am (Next day)

    The Tipp Tavern Photos

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    THE TIPP TAVERN ATMOSPHERE

    What's the vibe?
    Outdoor seating
    Happy hour specials

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    Recommended Reviews - The Tipp Tavern

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    Tara O.

    Great spot for a drink in the town of Windham. Lively atmosphere with pool table and darts and the service is always friendly and quick!

    a glass of water with a lime slice and a straw

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    1 year ago

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    1 year ago

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    4 months ago

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    2 months ago

    friendly service. Welcoming atmosphere. And great food. Love the lounge area with pool tables and other fun

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    8 months ago

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    Danielle F.

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    8 months ago

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    3 years ago

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    Danielle F.

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    2 years ago

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    7 months ago

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    Danielle F.

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    Danielle F.

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    Danielle F.

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    3 years ago

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    Danielle F.

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    Review Highlights - The Tipp Tavern

    The good amount of hand cut fries were a bit short, lightly salted.

    Mentioned in 2 reviews

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    Jimmy O'Connor's Windham Mountain - Burger

    Jimmy O'Connor's Windham Mountain

    3.5(34 reviews)
    0.5 mi
    $$

    Where "Old School" is the Only School…read more 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!

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

    Photos
    Jimmy O'Connor's Windham Mountain - Motel Room

    Motel Room

    Jimmy O'Connor's Windham Mountain - Motel Room

    Motel Room

    Jimmy O'Connor's Windham Mountain - The bar, john and patsy are the best

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    The bar, john and patsy are the best

    Lilly's Steaks & Cocktails - French onion soup

    Lilly's Steaks & Cocktails

    3.9(59 reviews)
    0.0 mi

    Lily Steaks & Cocktails came highly recommended by locals, so we were excited to give it a try. The…read moreinterior is stylish and welcoming, and the service throughout our meal was attentive and friendly. We ordered a variety of dishes from the menu, and while most things were enjoyable, the star of the meal--the 42 oz porterhouse--left us a bit underwhelmed. It had decent flavor, but it was served cold, which took away from the overall experience. We also asked for it to be sliced, but it came out only partially cut, which felt a bit odd and made it harder to share. While it's not on par with high-end steakhouses in Manhattan or Long Island, for what it is, Lily holds its own as a decent local spot. I'd definitely consider returning to give it another shot--there's potential here with a few tweaks.

    This restaurant has a nice rustic vibe, with lots of wood and custom accents. The wicker…read moregrasshopper, which serves as the hostess counter, is quite unique and memorable. Our meal here was a bit disappointing. Their menu is different from what was posted online. We came wanting to try the brussel sprouts. Online, they were described as crispy, but turned out to be roasted with pancetta. I was also eager to try the soft pretzel. Online, it mentioned it came with a three cheese sauce, but at the restaurant it was served with beer cheese, which I can't eat. The name of the restaurant literally has "cocktails" in it, but they were out of nearly all of their fall cocktails. That being said, we tried to redeem the experience. Our waitress was friendly and kindly let us know that the sulphur in the tap water might be irritating, so we ordered bottled. The house salad was nice and fresh, and I loved the tanginess of the lemon vinaigrette. The mac and cheese was a generous portion size. It was a bit bland and could've used a sharper cheese, but it was very creamy with a nice baked top layer. The broccoli side was tasty and well seasoned with garlic. The onion rings were very crispy and also a good portion. My husband had the New York steak and enjoyed how buttery it was. However, they initially forgot to bring him a steak knife and it was hard to flag down a waitress to get one. Overall, we left full, but our expectations were not quite met.

    Photos
    Lilly's Steaks & Cocktails
    Lilly's Steaks & Cocktails - Lobster risotto

    Lobster risotto

    Lilly's Steaks & Cocktails

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    Chicken Run Family Restaurant and Steak House - Just brownie side :)

    Chicken Run Family Restaurant and Steak House

    4.0(254 reviews)
    1.2 mi
    $$

    I have been here about 4 times the past two years. I recommend the burger, it was good. I got the…read morefried chicken and it was hammered, overcooked and dried out. I had the ribs once and they weren't great either. I really want to see how they cook steak so I will probalby get it next time. I like Hazy IPAs, I wish they would get Westkill or something similar and replace Fiddlehead. Fiddlehead is old school NEIPA. The prices are very good and I the atmosphere is family oriented and very friendly IMO. Whenever I'm in Windham this is where I go. I like the bar a lot if you want to just hang out and enjoy the scene. The outdoor area is really nice too when its not winter. It is definetly the best value in Windham.

    Since opening its doors in 2012, Chicken Run has become the de facto "living room" for the Northern…read moreCatskills. Whether you're coming off a long day at Hunter Mountain or just passing through Windham, this spot perfectly balances a rustic, family-friendly atmosphere with a menu that doesn't cut corners. The Butcher Steaks: This isn't just a "chicken joint." They take their beef seriously, offering fresh-cut, flame-grilled steaks like the 24oz Ribeye and NY Strip. They even age their own steaks in-house when available, resulting in a tender, seasoned-to-perfection cut that rivals high-end steakhouses but at much friendlier "mountain prices." The Signature Fried Chicken: This is the restaurant's namesake for a reason. The chicken is consistently hot, crispy, and juicy. Pro tip: Get the combo that comes with their special honey sauce and "cornbread cake." Dipping the savory, salty skin into that honey is a game-changer. BBQ Ribs: If you're looking for "fall-off-the-bone," you found it. Their ribs are slow-cooked and slathered in a rich, tangy sauce that requires a stack of napkins and zero regrets. Save room--or just admit you're having a second dinner--for the homemade desserts. Their dessert bar and soft-serve ice cream are staples, but the real magic happens in the summer (or around the outdoor firepits) with their S'mores kits. It's the perfect way to cap off a mountain day. With a massive backyard featuring a firepit, live music on the weekends, and a "come as you are" dress code, it's easily the best spot for big groups. The service is fast, the portions are massive, and the "old-school country" energy makes you feel like a local the moment you walk in.

    Photos
    Chicken Run Family Restaurant and Steak House
    Chicken Run Family Restaurant and Steak House - Brownie Sunday without whipped cream

    Brownie Sunday without whipped cream

    Chicken Run Family Restaurant and Steak House

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    The Tipp Tavern - irish_pubs - Updated June 2026

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