Guidebook for Canaan
Food Scene
Great for breakfast and lunch. The chef used to be at Canyon Ranch.
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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.
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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.
Very hip with great food on the main drag in Great Barrington.
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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!
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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.
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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.
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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.
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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.
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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.
Excellent NYC quality food. Sit in the bar area in the basement for cozy atmosphere.
Bimi's Canteen & Bar
Excellent NYC quality food. Sit in the bar area in the basement for cozy atmosphere.
Apple Tree Inn
Parks & Nature
Gorgeous place for all levels of hiking!
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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.
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Turn Park Art Space
2 Moscow RdVery cool art park. Next to Depot 6 coffee shop in West Stockbridge.
In the summer you can walk up the ski mountain. Beautiful views at the top.
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Bousquet Ski Area
101 Dan Fox DrIn the summer you can walk up the ski mountain. Beautiful views at the top.
Arts & Culture
Amazing place to learn about the Shakers and their way of life. Fabulous place to take kids. Very interactive and wonderfully preserved.
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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.
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
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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
Makumbusho ya Norman Rockwell
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.
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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 RdSummer home of The Boston Symphony. They also have fun pop concerts. Sit on the lawn and have a picnic. Check tanglewood dot org for the schedule.
Tanglewood
Summer home of The Boston Symphony. They also have fun pop concerts. Sit on the lawn and have a picnic. Check tanglewood dot org for the schedule.
Dr. Seuss National Memorial Sculpture Garden
21 Edwards StArt Omi
1405 Co Rte 22PS21: Performance Spaces for the 21st Century
2980 NY-66Drinks & 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!
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Balderdash Cellars
81 State RdGreat local winery with that view. They also have a good food truck. Dog friendly, too!
Mooncloud
47 Railroad StOn Great Barrington’s cool Railroad Street.
Cool local brewery in an Old school house. Great outdoor family area with food truck and Bocce courts.
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Roaring 20s Brewery & Taphouse
565 US-20Cool local brewery in an Old school house. Great outdoor family area with food truck and Bocce courts.
Entertainment & Activities
Cove Bowling Lanes
109 Stockbridge RdExcellent old school bowling alley.
Great seats, never crowded. $10 a seat, $7 for matinees
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Phoenix Theatres Beacon Cinema
57 North StGreat seats, never crowded. $10 a seat, $7 for matinees
Imperial Bowl
555 Dalton AveOld school bowling alley.
Jiminy Peak Mountain Adventure Park
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!