Guidebook for Canaan
Food Scene
Great for breakfast and lunch. The chef used to be at Canyon Ranch.
59 locals recommend
Blueberry Hill Market Cafe
515 US-20Great for breakfast and lunch. The chef used to be at Canyon Ranch.
Wood fired pizza and good family atmosphere. The wings are great, too, and they have a great on-tap beer selection.
12 locals recommend
M&M'S Tap and Tavern
501 US-20Wood fired pizza and good family atmosphere. The wings are great, too, and they have a great on-tap beer selection.
The Prairie Whale
178 Main StVery hip with great food on the main drag in Great Barrington.
Highly recommended. You can call ahead to (413) 274-1313 and order amazing bread, croissants, cookies, frozen pizza and chicken pot pies among other goodies and it’s a pretty ride to pick them up!
64 locals recommend
Berkshire Mountain Bakery Inc
367 Park StHighly recommended. You can call ahead to (413) 274-1313 and order amazing bread, croissants, cookies, frozen pizza and chicken pot pies among other goodies and it’s a pretty ride to pick them up!
Good Mexican food from the lady who owns Blueberry Hill. About a 15 minute drive from the cottage up Route 22. Call 518-755-1081 for pickup.
17 locals recommend
Norte Azul Cantina
15952 NY-22Good Mexican food from the lady who owns Blueberry Hill. About a 15 minute drive from the cottage up Route 22. Call 518-755-1081 for pickup.
Really great restaurant with an excellent takeout selection! Look for them on Instagram for the daily choices.
21 locals recommend
Pleasant and Main Cafe General Store
1063 Main StReally great restaurant with an excellent takeout selection! Look for them on Instagram for the daily choices.
About the best one stop shopping in Pittsfield for salads, sandwiches, bakery, pizza, milk, cheese, coffee....Really, really good.
19 locals recommend
Berkshire Mountain Bakery Pizza Cafe
180 Elm StAbout the best one stop shopping in Pittsfield for salads, sandwiches, bakery, pizza, milk, cheese, coffee....Really, really good.
Nice coffee spot with breakfast in West Stockbridge, MA.
82 locals recommend
No. Six Depot Roastery & Cafe
6 Depot StNice coffee spot with breakfast in West Stockbridge, MA.
Old Chatham Country Store & Cafe
639 Albany TurnpikeGreat spot for beer, cider, and really good Vietnamese/Thai food made fresh right there with great seating areas. Highly recommend.
The Greenhouse Cidery
Great spot for beer, cider, and really good Vietnamese/Thai food made fresh right there with great seating areas. Highly recommend.
Parks & Nature
Gorgeous place for all levels of hiking!
41 locals recommend
Mass Audubon's Pleasant Valley Wildlife Sanctuary
472 W Mountain RdGorgeous place for all levels of hiking!
Berkshire Botanical Garden
5 W Stockbridge RdThe Columbia Land Conservancy - https://clctrust.org/public-conservation-areas/ - has many gorgeous sites in Columbia County for bird watching, hiking, kayaking, etc.
Columbia Land Conservancy
49 Main StreetThe Columbia Land Conservancy - https://clctrust.org/public-conservation-areas/ - has many gorgeous sites in Columbia County for bird watching, hiking, kayaking, etc.
Very cool art park. Next to Depot 6 coffee shop in West Stockbridge.
10 locals recommend
Turn Park Art Space
2 Moscow RdVery cool art park. Next to Depot 6 coffee shop in West Stockbridge.
Arts & Culture
Tanglewood
Check for performance schedule and tickets at Tanglewood.org
Amazing place to learn about the Shakers and their way of life. Fabulous place to take kids. Very interactive and wonderfully preserved.
161 locals recommend
Hancock Shaker Village
1843 W Housatonic StAmazing place to learn about the Shakers and their way of life. Fabulous place to take kids. Very interactive and wonderfully preserved.
The first Shaker settlement in the area. Beautifully preserved buildings and exhibits.
18 locals recommend
Shaker Museum | Mount Lebanon
202 Shaker RdThe first Shaker settlement in the area. Beautifully preserved buildings and exhibits.
Naumkeag is a turn-of-the-century mansion in Stockbridge that is beautifully preserved. The surrounding gardens are also gorgeous. Well worth a visit: http://www.thetrustees.org/assets/documents/places-to-visit/trailmaps/Naumkeag-House-Gardens-Map.pdf
109 locals recommend
Naumkeag
5 Prospect Hill RdNaumkeag is a turn-of-the-century mansion in Stockbridge that is beautifully preserved. The surrounding gardens are also gorgeous. Well worth a visit: http://www.thetrustees.org/assets/documents/places-to-visit/trailmaps/Naumkeag-House-Gardens-Map.pdf
Norman Rockwell Museum
9 Glendale RdSummer home of the artist who carved the Lincoln statue at the Lincoln Memorial. Gorgeous grounds. His studio is still there with a lot of his other works.
63 locals recommend
Chesterwood
4 Williamsville RdSummer home of the artist who carved the Lincoln statue at the Lincoln Memorial. Gorgeous grounds. His studio is still there with a lot of his other works.
Turn Park Art Space
2 Moscow RdShopping
Guido's Fresh Marketplace
760 S Main StGreat gourmet market 15 minutes from the cottage.
Your basic, has everything supermarket. 15 miles west directly on Rte 295 in Chatham/Ghent NY.
65 locals recommend
Price Chopper
2614 NY-66Your basic, has everything supermarket. 15 miles west directly on Rte 295 in Chatham/Ghent NY.
Your basic has everything supermarket. In Pittsfield, very near to Guido's.
61 locals recommend
Stop & Shop
876 State RdYour basic has everything supermarket. In Pittsfield, very near to Guido's.
Drinks & Nightlife
Chatham Brewing
59 Main StGreat selection, good space, good food.
Great local winery with that view. They also have a good food truck. Dog friendly, too!
29 locals recommend
Balderdash Cellars
81 State RdGreat local winery with that view. They also have a good food truck. Dog friendly, too!
Cool local brewery with great outdoor area for families with food trucks and bocce courts.
11 locals recommend
Roaring 20s Brewery & Taphouse
565 US-20Cool local brewery with great outdoor area for families with food trucks and bocce courts.
Mooncloud
47 Railroad StOn Great Barrington’s cool Railroad Street.
Entertainment & Activities
Excellent old school bowling alley with a hilariously bad indoor miniature golf course attached to it. Hey, why not?
14 locals recommend
Cove Bowling Lanes
109 Stockbridge RdExcellent old school bowling alley with a hilariously bad indoor miniature golf course attached to it. Hey, why not?
Great seats, never crowded. $10 a seat, $7 for matinees
44 locals recommend
Phoenix Theatres Beacon Cinema
57 North StGreat seats, never crowded. $10 a seat, $7 for matinees
Imperial Bowl
555 Dalton AveCandle pin bowling in Pittsfield!
Cool local brewery in an Old school house. Great outdoor family area with food truck and Bocce courts.
11 locals recommend
Roaring 20s Brewery & Taphouse
565 US-20Cool local brewery in an Old school house. Great outdoor family area with food truck and Bocce courts.
Liquor stores
Doesn’t look like much on the outside but they have an Excellent wine selection (Italy, France, Spain, California), whiskey/bourbon, beer, hard to find European liqueurs....15% case discount. No tax on alcohol in Massachusetts!
Liquors Inc.
485 Dalton AveDoesn’t look like much on the outside but they have an Excellent wine selection (Italy, France, Spain, California), whiskey/bourbon, beer, hard to find European liqueurs....15% case discount. No tax on alcohol in Massachusetts!