Guidebook to Southern Berkshires
Food Scene
Great for a nice dinner. Reservations recommended on weekends and holidays.
75 locals recommend
Old Mill
53 Main StGreat for a nice dinner. Reservations recommended on weekends and holidays.
Black Rabbit
2 Ethan Allen StGreat lunch and brunch spot.
The Prairie Whale
178 Main StGreat farm to table restaurant in GB.
Best coffee in CT. They open 7am most days and 8am on Sunday.
23 locals recommend
Sweet William's Coffee Shop & Bakery
17 Main StBest coffee in CT. They open 7am most days and 8am on Sunday.
Don't lower your sushi expectations just because you are enjoying the mountains. Bizen in Great Barrington serves sushi that needs no excuses. It has a full menu of Japanese cuisine but honestly I go there for the sushi.
101 locals recommend
Bizen Gourmet Japanese Restaurant and Sushi Bar
17 Railroad StreetDon't lower your sushi expectations just because you are enjoying the mountains. Bizen in Great Barrington serves sushi that needs no excuses. It has a full menu of Japanese cuisine but honestly I go there for the sushi.
Great food and serves breakfast until 4pm! Beautiful views of the creek out back.
14 locals recommend
Mom's Country Cafe
65 Main StGreat food and serves breakfast until 4pm! Beautiful views of the creek out back.
Four Brothers
2828 NY-23Family owned local pizzeria and much more.
Great coffee, breakfast and sandwiches just minutes from our Sheffield cabin.
20 locals recommend
The Marketplace Kitchen and Cafe
18 Elm CtGreat coffee, breakfast and sandwiches just minutes from our Sheffield cabin.
Dad's Copake Diner
178 County Rte 7AIce cream stand around the back is a local favorite.
When all you need is a couple of slices of great pizza this is the spot. You can also order a whole pie to go. Best pizza for miles around - I’ve checked.
Tommy B's Slice Shop
When all you need is a couple of slices of great pizza this is the spot. You can also order a whole pie to go. Best pizza for miles around - I’ve checked.
Great authentic Mexican food. And wonderful people to boot.
52 locals recommend
Xicohtencatl Restaurant
50 Stockbridge RdGreat authentic Mexican food. And wonderful people to boot.
Drinks & Nightlife
The White Hart
15 Under Mountain RdGreat drinks and atmosphere just 15 mins from the cabin.
The Stagecoach Tavern
854 S Undermountain RdQuaint and cozy place to get a great drink and a burger.
Beautifully restored building with a brewery and food in the heart of Hillsdale.
51 locals recommend
Roe Jan Brewing Co.
32 Anthony StBeautifully restored building with a brewery and food in the heart of Hillsdale.
The Barn
17 Main StThe spot for live music and a good time in the Southern Berkshires.
Parks & Nature
Public beach and recreational area in Great Barrington. No resident permit needed.
49 locals recommend
Lake Mansfield Park
Lake Mansfield RoadPublic beach and recreational area in Great Barrington. No resident permit needed.
Lake Taghkanic State Park
1528 New York 82Beautiful lake and hiking trails.
Just a 5 min drive from the house sits this beautiful park with natural walking trails over rolling hills. A children’s playground and a separate dog park add to the appeal. In the summer the local farmers market is held in a barn at the entrance of the park.
12 locals recommend
Roeliff Jansen Park
116 Old Rte 22Just a 5 min drive from the house sits this beautiful park with natural walking trails over rolling hills. A children’s playground and a separate dog park add to the appeal. In the summer the local farmers market is held in a barn at the entrance of the park.
Harlem Valley Rail Trail
Arts & Culture
Extensive collection of Norman Rockwell covers and local history.
344 locals recommend
Norman Rockwell Museum
9 Glendale RdExtensive collection of Norman Rockwell covers and local history.
The Tanglewood Music Center is an annual summer music academy in Lenox, MA. The Center operates as a part of the Tanglewood Music Festival, an outdoor concert series and the summer home of the Boston Symphony Orchestra (BSO).
398 locals recommend
Tanglewood
The Tanglewood Music Center is an annual summer music academy in Lenox, MA. The Center operates as a part of the Tanglewood Music Festival, an outdoor concert series and the summer home of the Boston Symphony Orchestra (BSO).
Jacob's Pillow
358 George Carter RdBest of the Berkshires!
An open air museum like no other. Highly recommended for architecture aficionados.
310 locals recommend
Art Omi
1405 Co Rte 22An open air museum like no other. Highly recommended for architecture aficionados.
Essentials
Stop & Shop
55 Village Green DrLarge supermarket and household items.
Great local market close to the cabin with everything you need to prepare a gourmet meal.
23 locals recommend
LaBonne's Market
22 Academy StGreat local market close to the cabin with everything you need to prepare a gourmet meal.
Guido's Fresh Marketplace
760 S Main StGourmet marketplace just outside of Great Barrington.
Hillsdale Supermarket
2628 NY-23Great supermarket option close to Catamount.
Beautiful country store with and coffee shop that serves sandwiches plus a gourmet market where you can pickup everything for your meals.
31 locals recommend
Random Harvest
1785 NY-23Beautiful country store with and coffee shop that serves sandwiches plus a gourmet market where you can pickup everything for your meals.
Fruits, veggies and everything else you need to prepare a fancy meal. Many of the products are from local farms.
27 locals recommend
Copake General Store
171 Columbia County Rd 7AFruits, veggies and everything else you need to prepare a fancy meal. Many of the products are from local farms.
Sightseeing
Berkshire Botanical Garden
5 W Stockbridge RdYou can walk to the beginning of the Race Brook Falls trail in 10 minutes from the cabin.
22 locals recommend
Race Brook Falls
You can walk to the beginning of the Race Brook Falls trail in 10 minutes from the cabin.
Sheffield has it's own distillery about 10 mins from the cabin. It's open for tours starting every hour on Friday and Saturday (first tour is at 12:00 – last tour starts at 4:00). Tours are $10 per person. They last approximately one hour and end with tastings!
35 locals recommend
Berkshire Mountain Distillers
356 S Main StSheffield has it's own distillery about 10 mins from the cabin. It's open for tours starting every hour on Friday and Saturday (first tour is at 12:00 – last tour starts at 4:00). Tours are $10 per person. They last approximately one hour and end with tastings!
Visit their Tap Room, open from 12-6 on Thursdays, Fridays and Saturdays for pints and beer to go. They also do free tours on Saturdays. If you bring your growler they can filler-up.
31 locals recommend
Big Elm Brewing
65 Silver StVisit their Tap Room, open from 12-6 on Thursdays, Fridays and Saturdays for pints and beer to go. They also do free tours on Saturdays. If you bring your growler they can filler-up.
Beautiful waterfall and hike on the border of MA and NY.
282 locals recommend
Bash Bish Falls State Park
Falls RoadBeautiful waterfall and hike on the border of MA and NY.
Entertainment & Activities
Catamount Mountain Ski Resort
78 Catamount RdSki area just 15 minutes from the cabin.
Ski Butternut
380 State RdSki area 20 minutes from the cabin.
Mohawk Mountain Ski Area
46 Great Hollow RdSki mountain in CT, 35 minutes from the cabin.
Kripalu Center For Yoga & Health
57 Interlaken RdTheir 18-hole Golf Course is enveloped by the foothills of the Berkshire Mountains, the shores of Copake Lake, and the unparalleled vistas of Columbia County in upstate New York.
The Greens — its restaurant and bar serves club fare and finely prepared American cuisine. It's also a great place to relax by their outdoor fireplace and watch the sunset.
46 locals recommend
The Greens at Copake Country Club
44 Golf Course RdTheir 18-hole Golf Course is enveloped by the foothills of the Berkshire Mountains, the shores of Copake Lake, and the unparalleled vistas of Columbia County in upstate New York.
The Greens — its restaurant and bar serves club fare and finely prepared American cuisine. It's also a great place to relax by their outdoor fireplace and watch the sunset.