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    Nellie’s

    3.0 (6 reviews)
    Closed 4:00 pm - 9:00 PM

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    Jimmy O'Connor's Windham Mountain - Burger

    Jimmy O'Connor's Windham Mountain

    3.5(34 reviews)
    9.2 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!

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    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)
    9.4 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 - Lentil Soup

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    Lentil Soup

    Chieftans Restaurant & Bar - BEC Sandwich and a Mimosa. Available Sundays 12-4pm for Brunch

    Chieftans Restaurant & Bar

    3.8(126 reviews)
    29.6 mi
    $$

    Great location. Love the historical building. Food was really good. Beer was cold with great…read moreservice. Def recommend

    This place continues to underwhelm. The food is always just…read moreokay to good. Never great, never spectacular, never delicious. On our most recent visit, however, it was the service that was horrible. We didn't get the server that we often have, but we were willing to give a different server a chance. She. Was. Horrible. It took more than 15 minutes to get our soup and salad! My husband had to flag down the hostess to ask for a refill on my water, TWICE. The server never asked if I would like a refill and my meal was buffalo chicken!! As a matter of fact she never asked me anything, only my husband. "How's your meal?". "Would you like another drink (twice)?". "Do you need a carry out container?". All directed at only him. Then, to top it all off, she didn't come back to the table for a solid 10 minutes once we got our containers. She had us, one table that needed their order taken and a third table that was still looking at menus and she was flustered. Once we finally did see her she asked if we wanted anything else, again speaking directly to my husband! He said "Just the check, please." And here comes the best part, we watched her get drinks for her third table, take orders at the second table and walk by us at least six times. We waited nearly 15 minutes for her to bring the check. It was ridiculous. As I said, the food was good, at best. The service horrendous. Usually the food is nothing to write home about but the service is good. This visit was just BAD. We live less than a mile from this restaurant and still only go 2-3 times a year. That number will go down even more now.

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    Chieftans Restaurant & Bar
    Chieftans Restaurant & Bar - French onion soup

    French onion soup

    Chieftans Restaurant & Bar

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    The Cask and Rasher

    The Cask and Rasher

    4.1(119 reviews)
    13.5 mi
    $$

    If you are looking for an incredible couple who owns an amazing pub called Cask and Rasher and…read morecaters weddings with their unbelievable catering service called Fire Candy, look no further. From the moment we met Jocelyn and Jared and tasted their food, we knew they were the right caterers for us. From the freshly baked sourdough Roman-style pizza and the seafood paella to the fried chicken, brisket, and everything in between, these two know how to prepare amazing food for large groups of people, serve it fresh and hot, and make your wedding feel like their only priority. Let's start with the wedding itself. Their range of menu options and bar service is so vast that you will surely find what you're looking for. And if you don't, they are more than willing to adapt to your desires. We worked together to create the best menu for our big day and it came together perfectly. The photos you see online are real. The food is not only delicious but served beautifully. And they work with the Owls Hoot Barn (among other venues in the area) all the time so have everything perfectly coordinated with the venue. We also hosted our Friday night welcome party and Sunday family brunch at their pub, and it was the perfect location, set five minutes from where our guests were staying. They were so hospitable and accommodating and went the extra mile to prepare the venue for our guests and make it the most beautiful, special spot for these moments. Not to mention the food, which was amazing. Their fee includes everything, so there are absolutely no surprises. Their staff is wonderful. They do it all, from food to the bar, from small gatherings to large affairs. We feel like family and look forward to eating at their pub for many years to come. Thank you Jocelyn and Jared, for making our wedding weekend so special.

    The decor of The Cask and Rasher is old fashioned, authentic and wide-spaced. Their safe procedure…read moreof COVID-19 was well-planned, the staff wrote down the contact information of every customer and sanitized tables after dining. The staff was friendly. In order to keep social distance, customers need to order via scanning a QR code on each table to access the menu. There wasn't a great variety of options but enough as a bar. We had their Brisket Nacho, Smoked Drum and a side of salad. We love the brisket, which was cooked tender and flavorful. However the drum was kind of dry and hard to chew. Overall, the ambiance was great and the food was decent. It's a cozy and relaxing dining experience.

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    The Cask and Rasher
    The Cask and Rasher - Yum

    Yum

    The Cask and Rasher - Cojo and Area 51

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    Cojo and Area 51

    Nellie’s - bakeries - Updated July 2026

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