8 Best Cocktail Bars near Lenox

Cello Restaurant American • $$$
37 Church St, Lenox

Customers` Favorites

Roasted Striped Bass over Cauliflower Puree and Lima Beans
Pork Belly Tacos with Wasabi Crema
Fish Cake with Bacon Aioli
Chipotle Roasted Carrots
Pâté
Salads

“Visiting our daughter, we came to Cello for dinner…what an amazing choice!! From the moment you walk in, you are greeted by the warm smiles of both Kim and Ryan…the inviting smells of delicious food and the cozy atmosphere….from our drinks to the desserts, our experience was so wonderful! Starting with the warm corn bread and soft butter, the sweet and savory ribs, and the perfect stack of onion rings to the delicious homemade pasta dishes - the ramp pesto or the boar ragu——we are still raving about the amazing flavors! We will definitely be back!!!“

4.9 Superb94 Reviews
1894: A Miraval Experience Fine Dining
55 Lee Rd, Lenox

“Found this from online reviews and decided to try and was very happy we did. From the service to the food, you got the feeling that they really cared and delivered beyond. The servers and host were so genuinely friendly, interested, and timing was perfect, I was very impressed. And then each course was a true pleasure, delicious, surprising, and interesting flavor combinations, cooked to perfection. It was our 15th anniversary which I had written in our opentable reservation and they made sure to make it special for us above and beyond. From a fancy meal in the Berkshires at a very cool resort-like setting, I'd recommend trying it.“

4.2 Good9 Reviews
110 Grill American • $$
489 Pittsfield Rd, Lenox

Customers` Favorites

Fig and Prosciutto Flatbread
Pulled Pork Mac & Cheese
Crispy Fried Pickle Chips
Bang Bang Cauliflower
Pulled Pork Sandwich
BBQ Chicken Flatbread
Kale Brussels Salad
Gnocchi Bolognese
Loaded Tater Tots
Hot Honey Chicken

“Great food and service! This is our go to place. Tommy is an excellent server. All employees are friendly & professional. Manager always stops by the table to see if we are happy with our meral. I highly recommend going there !!!“

4.1 Good184 Reviews
The Lion's Den Bar • $$
The Red Lion Inn, 30 Main St, Stockbridge - 5.33 miles

Customers` Favorites

Corn Chowder
Clam Chowder

“Stopped in last night with my boyfriend and best friend 5/3/25 for a drink and lucked out with a lovely duo performance! My boyfriend used to come to the Red Lion Inn as a kid and he hadn't been in years. We had to stop in while we were in town and it was a very special moment. The only downside would be we only ordered the nuts and they took 30 minutes to come out. Seemed like our waiter was preoccupied with another table and we couldn't help but take notice. Our waiter, very tall slender looking man, was being disrespectful to a younger couple who was staying at the Inn for a weekend getaway. He was hitting on the girlfriend and openly crossing a boundary. The boyfriend even expressed to the waiter how uncomfortable he was that this is his girlfriend. He was asking the couple how they met and if they were even attracted to each other. It was incredibly uncomfortable and creepy to witness and I was appalled at the servers remarks to the couple. As someone who has been a waitress and a bartender, talking down to customers and hitting on their partner is so unbelievably unprofessional and I would be fired immediately. I am really hoping a consequence can come from this. Really upsetting way to leave such a gorgeous establishment with so many memories. Out of respect for this incredible establishment I gave it a 4 stars but it would've been a 5 otherwise.“

3.9 Good190 Reviews
Methuselah Bar and Lounge Wine Bar • $$
391 North St, Pittsfield - 6.95 miles

Customers` Favorites

Flourless Chocolate Cake
Sea Salt Caramel Gelato
BBQ Chicken & Onion
Marinated Olives
Pigs in a Blanket
Family Taco Night
Mushroom Tarts
Chicken Reuben
Chicken Tacos
Korean Kalbi

“Came here after checking in with our hotel quite late in the day. the place was clean and the atmosphere was great even though it was a monday night and there were many customers. service was amazing by the bartender Joshua. he was quite understanding after my lil trip up since Ive been drinking out in canada but Im not yet legal in the states, will be back when I am tho! the drinks he served were wonderful and the mocktail I got was delicious. The food from the kitchen was also amazing and we had the mushroom turnovers, bbq chicken & onion pizza, chicken reuben, and I had the korean kalbi. overall the night was good.“

4.5 Superb72 Reviews
101 Restaurant & Bar American • $$
1 West St, Pittsfield - 6.49 miles

Customers` Favorites

Fried Chicken Sandwich
Catfish Andouille Ragu
Chicken and Dumplings
Crawfish Mac & Cheese
Cajun Rubbed Salmon
Loaded Baked Potato
Smoked Pork Belly
Country Fried Pork
Shrimp and Grits
Fish and Chips

“I went to dinner last week with a friend and my significant other. Everything we had was delicious! Shrimp and grits were AMAZING! We also had pulled pork with the dirty rice. So good! Not to mention the drinks..... Craig served us amazing drinks!! We will be back“

4.1 Good45 Reviews
El Habanero Mexican Grill Pittsfield MA Mexican • $
685 Merrill Rd, Pittsfield - 8.56 miles

Customers` Favorites

Churros with Ice Cream
Chips and Salsa
Grande Burrito
Refried Beans
Taco Tuesday
Mexican Flan
Rice & Beans
Chimichanga
Tamales

“Every time I (or we) go, it’s always top notch! Food is flavorful and delicious. If shells are supposed to be crispy, they are CRISPY. Not soggy. Some of our favorites are the flautas, fajitas, tacos, taco salad & now enchiladas! The staff is always very friendly & attentive. Five stars!!“

3.8 Good44 Reviews
Sideline Saloon Bar • $
434 Fenn St, Pittsfield - 6.71 miles

“I've been in search for a great old throw back feel to Brooklyn Irish pubs. The great pubs are usully Irish ones. I found sideline and I must say with in minutes I felt a level of comfort. The owner Colleen was smart and engaging , fun to talk with.The GUINESS was the highlight for my husband it was perfect. There was no food but that didn't matter. The best Irish pubs have no food and offer good conversation and,the customers were filled with good conversation. I love this place. I will return to listen to their music when they have music. First time there but not the last time there. I was beginning to lose hope in finding a good Irish pub.I can't wait until football season to catch a game. They promised us the Steallers !! LolGreat establishment.Annie“

3 Average3 Reviews