Guidebook for Canaan
Food Scene
This lovely general store turns into a sophisticated American bistro on the weekends, boasting a nice wine list and locally sourced fair. Reservations are necessary.
9 locals recommend
Old Chatham
This lovely general store turns into a sophisticated American bistro on the weekends, boasting a nice wine list and locally sourced fair. Reservations are necessary.
Nothing chi-chi about this burger and beer joint. But it's got a lovely lake view and a casual, local vibe. The scallops wrapped in bacon are a sinful treat.
6 locals recommend
Backwater Grille
42 Queechy Lake DrNothing chi-chi about this burger and beer joint. But it's got a lovely lake view and a casual, local vibe. The scallops wrapped in bacon are a sinful treat.
Housed in an atmospheric, historical landmark building in the center of Chatham, this nice, mid-priced restaurant is hit and miss on the food front, but convenient. Nice bar setting in the basement.
68 locals recommend
Blue Plate
1 Kinderhook StHoused in an atmospheric, historical landmark building in the center of Chatham, this nice, mid-priced restaurant is hit and miss on the food front, but convenient. Nice bar setting in the basement.
Always lively, this old standard in Hudson is where all the locals gather. It's especially merry in the colder months.
65 locals recommend
Red Dot Bar & Restaurant
321 Warren StAlways lively, this old standard in Hudson is where all the locals gather. It's especially merry in the colder months.
Lovely room; inventive, locally sourced menu; cheerful staff; easy access. Highly recommended.
79 locals recommend
Local 111
111 Main StLovely room; inventive, locally sourced menu; cheerful staff; easy access. Highly recommended.
I'm a sucker for most anything French and this place, with it's specially imported bread oven—not to mention head baker—is the real deal.
101 locals recommend
Le Perche
230 Warren StI'm a sucker for most anything French and this place, with it's specially imported bread oven—not to mention head baker—is the real deal.
Arts & Culture
What can we say? This is one of those memorable experiences you shouldn't miss if you're visiting in high summer. Pack a picnic, chill some wine, and borrow our crystal candleholders.
15 locals recommend
Tanglewood Lions Gate
Hawthorne RoadWhat can we say? This is one of those memorable experiences you shouldn't miss if you're visiting in high summer. Pack a picnic, chill some wine, and borrow our crystal candleholders.
Having been both an audience member and a performer at Shakespeare & Co., I can't recommend this theatrical experience enough.
134 locals recommend
Shakespeare & Company
70 Kemble StHaving been both an audience member and a performer at Shakespeare & Co., I can't recommend this theatrical experience enough.
Contemporary art enthusiasts: Don't miss it! The 45-minute drive to North Adams is scenic and pleasant, plus the facility and various collections will knock your socks off.
382 locals recommend
MASS MoCA
1040 Mass MoCA WayContemporary art enthusiasts: Don't miss it! The 45-minute drive to North Adams is scenic and pleasant, plus the facility and various collections will knock your socks off.
Contemporary, impressionist, modern, this art museum has something for every inclination. The setting is pretty spectacular, as well. We often go on rainy days. Wonderful.
329 locals recommend
The Clark Art Institute
225 South StContemporary, impressionist, modern, this art museum has something for every inclination. The setting is pretty spectacular, as well. We often go on rainy days. Wonderful.
Berkshire Museum
39 South StGreat rainy day fallback, especially for kiddos.
You don't have to be passionate about the dance to appreciate this incredible venue, nestled against a majestic mountain backdrop. I go for the ballet and tango, my husband joins me for the setting.
257 locals recommend
Jacob's Pillow
358 George Carter RdYou don't have to be passionate about the dance to appreciate this incredible venue, nestled against a majestic mountain backdrop. I go for the ballet and tango, my husband joins me for the setting.
Shopping
The lovely Sandy Klempner has an unbeatable eye for design and her eclectic, West Stockbridge antiques store is a delight to visit. Some great deals to be had, as well! Some of our most treasured pieces are from her! sandyklempnerathome.com
Sandy Klempner Antiques & Interiors
22 Main StThe lovely Sandy Klempner has an unbeatable eye for design and her eclectic, West Stockbridge antiques store is a delight to visit. Some great deals to be had, as well! Some of our most treasured pieces are from her! sandyklempnerathome.com
Everything Else
One of our favorite conservation areas to hike in, Hand Hollow is an easy meander for little ones, yet scenic enough to keep adults entertained.
28 locals recommend
Hand Hollow Conservation Area
4079 County Rd 9One of our favorite conservation areas to hike in, Hand Hollow is an easy meander for little ones, yet scenic enough to keep adults entertained.
One of my favorite places in the world. 'nough said.
63 locals recommend
Ooms Conservation Area at Sutherland Pond
480 Rock City RdOne of my favorite places in the world. 'nough said.
Columbia Memorial Hospital
71 Prospect AveSecondary hospital option
We don't downhill ski, but if you do, you can practically roll out of bed and go here. Also, great tubing for the little ones.
115 locals recommend
Bousquet Ski Area
101 Dan Fox DrWe don't downhill ski, but if you do, you can practically roll out of bed and go here. Also, great tubing for the little ones.
A pretty drive south, this is slightly more challenging skiing then the much closer Bosquet.
329 locals recommend
Catamount Mountain Ski Resort
78 Catamount RdA pretty drive south, this is slightly more challenging skiing then the much closer Bosquet.
Jiminy Peak
37 Corey RdFor more serious skiers. We here tell it's great.
This easily negotiated, 10-foot wide, paved trail passes through the Hoosic River Valley, between Mount Greylock and the Hoosac Mountain Ranges. Stunning views. Great for all levels.
74 locals recommend
Ashuwillticook Rail Trail
Rail TrailThis easily negotiated, 10-foot wide, paved trail passes through the Hoosic River Valley, between Mount Greylock and the Hoosac Mountain Ranges. Stunning views. Great for all levels.
Sightseeing
The site of one of the first and largest Shaker settlements, this historical gem is a must-visit for lovers of history, American design, and students of world religions.
161 locals recommend
Hancock Shaker Village
1843 W Housatonic StThe site of one of the first and largest Shaker settlements, this historical gem is a must-visit for lovers of history, American design, and students of world religions.
Yes, it's a bit out of the way just to pick up a pint of (AMAZING) ginger yogurt, but it's well worth the visit. Children will especially love visiting the baby lambs in the springtime.
12 locals recommend
Old Chatham Sheepherding Company
155 Shaker Museum RdYes, it's a bit out of the way just to pick up a pint of (AMAZING) ginger yogurt, but it's well worth the visit. Children will especially love visiting the baby lambs in the springtime.