Drinks & Nightlife
Moe's Tavern is a must stop for 21+ who enjoy craft beer and an alternative environment to the typical bars found in the area. A hit amongst locals and travelers alike, it has been featured in the New York Times and been voted one of Massachusetts 14 best bars outside of Boston!
19 locals recommend
Moe's Tavern
10 Railroad StMoe's Tavern is a must stop for 21+ who enjoy craft beer and an alternative environment to the typical bars found in the area. A hit amongst locals and travelers alike, it has been featured in the New York Times and been voted one of Massachusetts 14 best bars outside of Boston!
Food Scene
Joe's Diner is a classic American diner and is known internationally for being featured in Norman Rockwell's paintings depicting American culture.
10 locals recommend
Joe's Diner
85 Center StJoe's Diner is a classic American diner and is known internationally for being featured in Norman Rockwell's paintings depicting American culture.
Betty's is a family favorite for Pizza. The Shack has a summer surfer vibe which is really fun for all ages. The pizza is stellar too.
13 locals recommend
Betty's Pizza Shack
26 Housatonic StBetty's is a family favorite for Pizza. The Shack has a summer surfer vibe which is really fun for all ages. The pizza is stellar too.
Just the best place around town from brunch all the way through to a late night drink at the bar. All local and fresh food. The vibe is relaxed but prices reflect the quality of food and drinks you'll get at the place.
203 locals recommend
The Prairie Whale
178 Main StJust the best place around town from brunch all the way through to a late night drink at the bar. All local and fresh food. The vibe is relaxed but prices reflect the quality of food and drinks you'll get at the place.
Authentic Mexican cuisine from mostly the central region of the country, very good!
52 locals recommend
Xicohtencatl Restaurant
50 Stockbridge RdAuthentic Mexican cuisine from mostly the central region of the country, very good!
Haven
8 Franklin StBreakfast and brunch favorite for locals and visitors alike!
Arts & Culture
Norman Rockwell was an iconic painter from the 20th century who is known internationally for his artwork which was featured as the cover for time magazine numerous times.
343 locals recommend
Norman Rockwell Museum
9 Glendale RdNorman Rockwell was an iconic painter from the 20th century who is known internationally for his artwork which was featured as the cover for time magazine numerous times.
Tanglewood is one if the Berkshires most notable attractions. The Summer home to the Boston Symphony Orchestra there are none stop concerts at the venue, it is both an indoor and outdoor concert call, most will bring a blanket food and drink and enjoy whomever is preforming under the stars. They have much more than classical as well!
394 locals recommend
Tanglewood
Tanglewood is one if the Berkshires most notable attractions. The Summer home to the Boston Symphony Orchestra there are none stop concerts at the venue, it is both an indoor and outdoor concert call, most will bring a blanket food and drink and enjoy whomever is preforming under the stars. They have much more than classical as well!
One of the main Theater venues in the Berkshires!
10 locals recommend
Barrington Stage Company: The Blatt Center
36 Linden StOne of the main Theater venues in the Berkshires!
Host a variety of different performances throughout the year some formal some very informal!
134 locals recommend
Shakespeare & Company
70 Kemble StHost a variety of different performances throughout the year some formal some very informal!
Amazing Dance performance venue, with free public shows available. Check their website for details....
https://www.jacobspillow.org/
257 locals recommend
Jacob's Pillow
358 George Carter RdAmazing Dance performance venue, with free public shows available. Check their website for details....
https://www.jacobspillow.org/
Shopping
The Prime Outlets are a huge hit among shoppers, myself included, for great deals and tons of variety.
155 locals recommend
Lee Premium Outlets
17 Premium Outlet BoulevardThe Prime Outlets are a huge hit among shoppers, myself included, for great deals and tons of variety.
Entertainment & Activities
Great skiing for the whole family with one of the top rated terrain parks in Massachusetts for those who freestyle ski.
218 locals recommend
Ski Butternut
380 State RdGreat skiing for the whole family with one of the top rated terrain parks in Massachusetts for those who freestyle ski.
Great skiing especially at night! Fun fact Bousquet was the first ski mountain to have night skiing under the lights in the entire country.
They have a great Thursday night skiing deal.
115 locals recommend
Bousquet Ski Area
101 Dan Fox DrGreat skiing especially at night! Fun fact Bousquet was the first ski mountain to have night skiing under the lights in the entire country.
They have a great Thursday night skiing deal.
The Triplex Cinema
70 Railroad StFun little theater in Great Barrington.
Phoenix Theatres Beacon Cinema
57 North StGreat theater with giant reclining seats.
Parks & Nature
Mount Greylock is Massachusetts highest peak. Has day hiking, overnight camping spots, you can drive to the top and locals love to bike up it if you're up for the challenge! also part of the Appalachian trail.
213 locals recommend
Mount Greylock
Mount Greylock is Massachusetts highest peak. Has day hiking, overnight camping spots, you can drive to the top and locals love to bike up it if you're up for the challenge! also part of the Appalachian trail.
Great little hike with stunning views of the Southern Berkshires. Perfect for those who was some physical activity before going into Great Barrington. Locals are obsessed!
112 locals recommend
Monument Mountain Reservation
Great little hike with stunning views of the Southern Berkshires. Perfect for those who was some physical activity before going into Great Barrington. Locals are obsessed!
Olivia's Overlook is a family favorite. It's a stunning view of the Stockbridge bowl (lake) with great little hiking trails, one which has a beautiful spot for a sunset hike!
51 locals recommend
Olivia's Overlook
Hiking TrailsOlivia's Overlook is a family favorite. It's a stunning view of the Stockbridge bowl (lake) with great little hiking trails, one which has a beautiful spot for a sunset hike!