at Monument Mountain, Route #7,
Looking for a great drink or watering hole after a long day of exploring the Berkshires? With so much to do here, there’s no doubt that you’ll need to refuel. Skip the crowds at the touristy spots and experience the area like a local—here’s our list of the best bars to visit in Great Barrington, MA.
Mixologist Billy Jack Paul and Chefs Josh and Emily Irwin have come together to create this unique cocktail bar and lounge that features elevated artistry and flavors in creative cocktails and locally sourced cured meats. Mooncloud is known as one of the best bars in Great Barrington, MA, and is as intriguing as it sounds: a visit to this comfortable and seductive lounge atmosphere will get your creative juices flowing.
This local watering hole features an extensive menu (and we do mean extensive!) as well as a full on-tap beer list with ciders, IPAs, ales, and more both locally and internationally brewed. Hit the pool table, choose from their rotating seasonal selection of beers, and snack on anything from pot stickers and shrimp cocktails to fried pickles and french onion soup.
If you’re a whiskey lover and looking to warm up after a long day of exploring, this local favorite is the perfect place for you to take a load off as it features Jameson Limited Reserve, Angel’s Envy, and Blanton’s Original. The Well in Great Barrington is a pub-inspired restaurant located right on Main Street with a menu that includes local grass-fed burgers, fresh salads, and classic bar food. Visit in the summer months to dine on their patio and enjoy ideal New England weather.
This delicious Mexican restaurant knows how to bring a party. With a large menu and a full bar, there’s no doubt you’ll be able to find a dish you love as soon as you take a peek at the menu. Having been thriving in the area for the past 15 years (and even claims to have the best margarita in the Berkshires), this eatery has perfected its cuisine to the point where you’ll want to come back two nights in a row.
This upscale eatery features signature cocktails, craft beer, and an extensive wine cellar. At cafe ADAM in Great Barrington, dining is more than a daily activity, it’s an experience meant to be savored and enjoyed. They search tirelessly for better and more delicious ingredients while locally sourcing their food from Berkshires farmers, artisan bakers, food crafters, mongers, brewers, distillers, and curators. Visit for a unique food and drinking pairing experience that’ll have your taste buds feeling reborn.
After a full day of an exciting new adventure, Briarcliff Motel will be ready to welcome you back to your home away from home. Explore all that Great Barrington has to offer this season—and don’t forget your pup! Book your stay.