21 Best Bars near Lenox

“We never go wrong when we head to the Olde Heritage Tavern. Great food & drinks, great service, great atmosphere!“

“gorgeous, well-maintained grounds, serene well-sited pool with a view and surrounded by flower gardens, comfortable beds and room, and charming reception area. Not to mention the location within walking distance of both Tanglewood and Kripalu. The breakfast was surprisingly lackluster and available only 8-10, but overall it was the perfect stay and we will definitely be back.“

“The food was great and the service was even better. Jake went out of his way to make us feel welcomed and comfortable. He offered advice on food selection and was attentive to our every need. He is the kind of person that you want as the example of the kind of staff that you hire. We'll be back again. Thanks Jake, and all the staff at Antimony.“

“My wife and I stopped in for Valentine’s Day last night and were reminded why Brava is the best restaurant in the Berkshires. We have been three times and every time we go we are impressed. Initially we were hesitant, thinking it would be over priced but it is always less expensive than we expected. Pizzas, wings, and the bread pudding were the favorites this time. 10/10.“

“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.“

“The BEST thing to happen in Housatonic forever!! Thank you Krissy and your wonderful gang for having such a friendly, welcoming bar with great food and one of the best draft beer lineups around. I might come back tomorrow... and the next day!“

“Sherry was great she made great drinks“

“It's a nice place, but just be warned that it's a Beer & Whiskey bar. They have very limited mixers, so very limited cocktail options. If you're a Beer and/or Whiskey fan, you'll enjoy it. They had one option each for Red & White wine in case there's a wine drinker in your group.“

“Great friendly staff. Love the cocktails. Nice cozy spot. Now they have pizza. Every one I tried is wonderful. My favorite stop when I am in Pittsfield.“

“Great staff! Good times! Love the place !“

“nice little hole in the wall bar“

“Great food but everything costs extra. Bought $67 worth of food which included 3lbs of wings for about $30-$32. Only comes with two sauces. The ranch wasn’t filled and didn’t go as far as it needed to. I will not pay $1 extra for more when you can get a bottle for about that.“

“First time to the Dream Away Lodge and it did not disappoint. Food was great, wait staff was very attentive, music was a good time. Highly recommend to anyone pass through the Berkshires. Can’t wait to go back!!“

“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.“

“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“

“Stopped here for lunch on the way back to Amsterdam NY, from Boston. We sat at the bar as we usually do everywhere. The service was excellent, the food came out fast and it was delicious. Will go back for sure.“

“I was born and raised in the Berkshires and this place always tastes like home! Every region has their niche and this is the niche of western Massachusetts. If you’re expecting a hot dog approved by Gordon Ramsay, look elsewhere. If you enjoy great flavor and an atmosphere that is very small town local, this is your place! Anyone from this area doesn’t need to google the best hot dog spot, we know where to go. Teos.“

“We were there in June. Food was great. Very friendly the owners gave us a jar of their spaghetti sauce. Delicious.“

“The new addition of Shabu (hot pot) is a refreshing option to the mundane offerings of most Pittsfield restaurants. Delicious and huge portions! Will be going again soon! I recommend to everyone!“

“On our way home from drone daughter off at camp we stopped in. I got the brisket and rib combo. My wife got the burger. We got a pretzel and Mediterranean snack. It was all delicious. Friendly staff and nice atmosphere. I will go again.“