Sightseeing
One of the best things to do in the area, hands down! Their cafe is really fantastic, as well (love their coffee!)
310 locals recommend
Art Omi
1405 Co Rte 22One of the best things to do in the area, hands down! Their cafe is really fantastic, as well (love their coffee!)
Stockbridge is pretty close, and what a fun opportunity to check out some great artwork!
343 locals recommend
Norman Rockwell Museum
9 Glendale RdStockbridge is pretty close, and what a fun opportunity to check out some great artwork!
This is basically just in our backyard, often open seasonally, it's definitely worth a visit!
6 locals recommend
Austerlitz Historical Society
11550 New York 22This is basically just in our backyard, often open seasonally, it's definitely worth a visit!
Great hiking, and literally just up the hill (er...mountain) from us!
9 locals recommend
Harvey Mountain State Forest
Great hiking, and literally just up the hill (er...mountain) from us!
Just a quick drive away, take in Edith Wharton's Home!
167 locals recommend
The Mount, Edith Wharton's Home
2 Plunkett StJust a quick drive away, take in Edith Wharton's Home!
Du Bois Boyhood Homesite (or W.E.B. Du Bois Homesite) is a National Historic Landmark in Great Barrington, Massachusetts, commemorating an important location in the life of African American intellectual and civil rights activist W.E.B.
12 locals recommend
W.E.B. Du Bois National Historic Site
612 S Egremont RdDu Bois Boyhood Homesite (or W.E.B. Du Bois Homesite) is a National Historic Landmark in Great Barrington, Massachusetts, commemorating an important location in the life of African American intellectual and civil rights activist W.E.B.
Gorgeous place to spend the day, we love this historic home, and nearby Stockbridge is such an adorable town to walk around.
109 locals recommend
Naumkeag
5 Prospect Hill RdGorgeous place to spend the day, we love this historic home, and nearby Stockbridge is such an adorable town to walk around.
Odds & Ends
Beebe Hill State Forest
County Route 5Great hiking area!
In the event that you need to mail anything, the post office is just a few minutes away! It's adorable.
6 locals recommend
United States Postal Service
1961 NY-295In the event that you need to mail anything, the post office is just a few minutes away! It's adorable.
Walgreens
19 Central AveForget something? Walgreens in nearby Chatham has you covered!
Need some groceries? Head to Price Chopper (they're open late if you need to make a quick run!)
65 locals recommend
Price Chopper
2614 NY-66Need some groceries? Head to Price Chopper (they're open late if you need to make a quick run!)
Crandell Theatre
48 Main StGreat spot to go to catch a movie!
Shakespeare & Company is about 20 minutes away, check out their season!
134 locals recommend
Shakespeare & Company
70 Kemble StShakespeare & Company is about 20 minutes away, check out their season!
Chatham Wine & Liquor
53 Main StGreat local wine shop!
Shaker Mill Books
3 Depot StGreat bookstore in nearby West Stockbridge!
Calyx Berkshire Dispensary
Really excellent dispensary in Great Barrington!
Venture off the beaten path to Hoffman Pottery and be enchanted by a magical forest of works that "dance with energy." Elaine Hoffman's unique feeling for form and multi-layered decoration create a rhythm all their own.
Hoffman Pottery-W Stockbridge
103 Great Barrington RdVenture off the beaten path to Hoffman Pottery and be enchanted by a magical forest of works that "dance with energy." Elaine Hoffman's unique feeling for form and multi-layered decoration create a rhythm all their own.
Shaker Mill Books is the "retirement" project of Eric Wilska - former owner of the Bookloft for 42 years - selling new, used, rare and out-of-print books. They have an extensive collection of art, architecture and photography books to complement their unparalleled selection of books on and about the Berkshires. Spend a leisurely afternoon browsing the collection and enjoying the deck overlooking the river.
Shaker Mill Books
3 Depot StShaker Mill Books is the "retirement" project of Eric Wilska - former owner of the Bookloft for 42 years - selling new, used, rare and out-of-print books. They have an extensive collection of art, architecture and photography books to complement their unparalleled selection of books on and about the Berkshires. Spend a leisurely afternoon browsing the collection and enjoying the deck overlooking the river.
This funky country store also sells old-time toys, candies, baking ingredients, greeting cards, and miscellaneous sundries. Check out their old-time photo booth!
6 locals recommend
Charles H. Baldwin & Sons
1 Center StThis funky country store also sells old-time toys, candies, baking ingredients, greeting cards, and miscellaneous sundries. Check out their old-time photo booth!
PS21: Performance Spaces for the 21st Century
2980 NY-66Great performance space in Chatham
Crandell Theatre
48 Main StFancy a movie? Here's your spot!
Stone Corner Minerals
Lovely spot for an lux earthy souvenir
Tanglewood is a music venue that’s considered a local gem in Lenox. It’s the summer home to the Boston Symphony Orchestra and hosts the extremely popular Tanglewood Music Festival.
Tanglewood
Tanglewood is a music venue that’s considered a local gem in Lenox. It’s the summer home to the Boston Symphony Orchestra and hosts the extremely popular Tanglewood Music Festival.
Neighborhoods
Lenox is just a close drive away, so many great restaurants, cafes, shops, & galleries. Check it out if you're looking for a fun outing!
85 locals recommend
Lenox
Lenox is just a close drive away, so many great restaurants, cafes, shops, & galleries. Check it out if you're looking for a fun outing!
Charming town with great views, nice restaurants & a little shopping
19 locals recommend
West Stockbridge
Charming town with great views, nice restaurants & a little shopping
Great Barrington is a great place to go for a bite to eat, shops, culture, & more!
188 locals recommend
Great Barrington
Great Barrington is a great place to go for a bite to eat, shops, culture, & more!
Food scene
Our Daily Bread Deli
116 Hudson AveWe love this place! Great for breakfast/brunch.
Blue Plate
1 Kinderhook StGreat spot to have a nice dinner.
Chatham Brewing
59 Main StDefinitely a local favorite!
Excellent local coffee shop. Outdoor tables, great place to sit & write.
82 locals recommend
No. Six Depot Roastery & Cafe
6 Depot StExcellent local coffee shop. Outdoor tables, great place to sit & write.
Great spot for a nice dinner in Lenox. Really friendly staff and big plates!
7 locals recommend
Prime Italian Steakhouse & Bar
15 Franklin StGreat spot for a nice dinner in Lenox. Really friendly staff and big plates!
feast & floret
#Nomnom
Amici is a casual Italian restaurant serving simple good comfort food at approachable prices, in a warm and friendly atmosphere. Large outdoor patio & lounge.
AMICI
Amici is a casual Italian restaurant serving simple good comfort food at approachable prices, in a warm and friendly atmosphere. Large outdoor patio & lounge.
The Mazzeo family has been serving up old school Italian classics for nearly half a century. They are famous for their eggplant parmesan and cavatelli, a thin shell pasta featured in a variety of main dishes, lovingly made by the family matriarch. The robust menu also includes a variety of meat, seafood and other Italian classics. Reservations recommended.
34 locals recommend
Mazzeo's Ristorante
1015 South StThe Mazzeo family has been serving up old school Italian classics for nearly half a century. They are famous for their eggplant parmesan and cavatelli, a thin shell pasta featured in a variety of main dishes, lovingly made by the family matriarch. The robust menu also includes a variety of meat, seafood and other Italian classics. Reservations recommended.
Chef Davide Manzo has created one of the most romantic and beautiful restaurants in the Berkshires. Enjoy sophisticated southern Italian fare in a lantern-lit, brick-and-stone interior, featuring specialties cooked in a wood-fired oven. Delightful alfresco dining in season.
22 locals recommend
Trattoria Rustica
27 Mc Kay StChef Davide Manzo has created one of the most romantic and beautiful restaurants in the Berkshires. Enjoy sophisticated southern Italian fare in a lantern-lit, brick-and-stone interior, featuring specialties cooked in a wood-fired oven. Delightful alfresco dining in season.
Yummy Japanese in Great Barrington
101 locals recommend
Bizen Gourmet Japanese Restaurant and Sushi Bar
17 Railroad StreetYummy Japanese in Great Barrington
Lunch, anyone? Yummy spot to grab a sandwich or a quick bite.
18 locals recommend
Main St Goodness, home of PieconicNY bakery
20 Main StLunch, anyone? Yummy spot to grab a sandwich or a quick bite.
Bimi's Cheese Shop
21 Main StExcellent spot to stock your cheese board!
Rubiner's Cheesemongers
264 Main StThe go to spot for fancy cheese in Great Barrington
The best spot for apple picking in the Berkshires...and a lovely shop for quick farm to table bites.
27 locals recommend
Bartlett's Orchard
575 Swamp RdThe best spot for apple picking in the Berkshires...and a lovely shop for quick farm to table bites.
Visit this 100-year-old, family run orchard with breathtaking views of three states. Plan a day or an afternoon of apple cider sipping, wine tasting, cider donut eating, cidery touring, hiking, strolling, relaxing and rejuvenating at the foothills of the Berkshires.
41 locals recommend
Hilltop Orchards Home of Furnace Brook Winery
508 Canaan RdVisit this 100-year-old, family run orchard with breathtaking views of three states. Plan a day or an afternoon of apple cider sipping, wine tasting, cider donut eating, cidery touring, hiking, strolling, relaxing and rejuvenating at the foothills of the Berkshires.
Once Upon a Table
36 Main StExcellent brunch/lunch spot in Stockbridge!
Skiing/Snowboarding
Butternut Basin
Looking for a fun ski hill? Check out Butternut!
Catamount Mountain Ski Resort
78 Catamount RdAnother great skiing option!
Bousquet Mountain Ski Area
101 Dan Fox DrivePopular ski area in the Berkshires
City/town information
Hudson is really close, especially if you're coming to/from NYC. Lots to see and do!
440 locals recommend
Hudson
Hudson is really close, especially if you're coming to/from NYC. Lots to see and do!