The Berkshires Best Guidebook

Dan
The Berkshires Best Guidebook

Food scene

Organic and local crepes, sandwich’s, salads and more. Vegan and gluten free options. Good coffee, tea, and smoothies. Can be busy in peak times but we’ll worth the wait.
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Starving Artist Creperie and Cafe
40 Main St
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Organic and local crepes, sandwich’s, salads and more. Vegan and gluten free options. Good coffee, tea, and smoothies. Can be busy in peak times but we’ll worth the wait.
Good coffee
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Fuel Bistro/ Coffee Shop
293 Main St
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Good coffee
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Berkshire Mountain Distillers
356 S Main St
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Hilltop Orchards Home of Furnace Brook Winery
508 Canaan Rd
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Bizen Gourmet Japanese Restaurant and Sushi Bar
17 Railroad Street
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The Prairie Whale
178 Main St
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Rubiner's Cheesemongers
264 Main St
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The Old Inn On The Green
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*Seasonal only. High quality roadside spot. Burgers, fries, and some creative other options. Big outdoor space for frisbee, etc. Long lines in peak times so be prepared to wait.
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The Bistro Box
937 S Main St
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*Seasonal only. High quality roadside spot. Burgers, fries, and some creative other options. Big outdoor space for frisbee, etc. Long lines in peak times so be prepared to wait.
Recently open seasonally. Call before heading there. Coffee and drinks only.
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No. Six Depot Roastery & Cafe
6 Depot St
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Recently open seasonally. Call before heading there. Coffee and drinks only.
Great coffee. No food served.
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Lenox Coffee
52 Main St
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Great coffee. No food served.
A great coffee stop on your way to northern destinations
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Dotties Coffee Lounge
444 North St
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A great coffee stop on your way to northern destinations
Ice cream and shop. Local farm to come ice cream. Jersey cows you can see up close.
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High Lawn Farm
535 Summer St
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Ice cream and shop. Local farm to come ice cream. Jersey cows you can see up close.
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Lucky's Ice Cream & Grill
30 W Center St
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District Kitchen & Bar
40 West St
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Cafe Adam, Bar and Restaurant
420 Stockbridge Rd
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Ayelada
505 East St
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Great Barrington Bagel Company
777 S Main St
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A really nice lounge atmosphere in downtown Great Barrington with high end cocktails and light fare.
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Mooncloud
47 Railroad St
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A really nice lounge atmosphere in downtown Great Barrington with high end cocktails and light fare.
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Cantina 229
229 Hartsville-New Marlborough Rd
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Outdoors

Outdoor activities and things to do
Cold swim holes on hot days. The Green River is a great spot to cool down.
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Green River
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Cold swim holes on hot days. The Green River is a great spot to cool down.
A popular hiking destination with two ways up. Head left from the bottom for a longer more gentle hike. The top has expansive views and some areas with shear cliff drops. Best to keep dogs leashed and kids close.
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Monument Mountain
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A popular hiking destination with two ways up. Head left from the bottom for a longer more gentle hike. The top has expansive views and some areas with shear cliff drops. Best to keep dogs leashed and kids close.
Activities available in the summer, fall, and winter
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Catamount Mountain Ski Resort
78 Catamount Rd
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Activities available in the summer, fall, and winter
A family friendly local resort with tubing and skiing/snowboarding
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Ski Butternut
380 State Rd
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A family friendly local resort with tubing and skiing/snowboarding
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Jiminy Peak
37 Corey Rd
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Very good mountain bike trails and frisbee golf course. Brewery with outdoor seating and a few fire pits. Note there are no rentals so you have to bring your own gear.
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Norbrook Farm Brewery
204 Stillman Hill Rd
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Very good mountain bike trails and frisbee golf course. Brewery with outdoor seating and a few fire pits. Note there are no rentals so you have to bring your own gear.
Head into the New York State entrance side for a nice long gentle hike on man-made paths that are also accessible for strollers and wheelchairs
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Bash Bish Falls State Park
Falls Road
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Head into the New York State entrance side for a nice long gentle hike on man-made paths that are also accessible for strollers and wheelchairs
Cold river swimming with fun little waterfalls. Usually a pretty quiet place. Stop at the Southfield Store before or after for food and drinks.
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Umpachene Falls Park
Umpachene Falls Road
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Cold river swimming with fun little waterfalls. Usually a pretty quiet place. Stop at the Southfield Store before or after for food and drinks.
Nice easy hike. 20 mins. The glen has a windy trail that you need to scuttle through but is nice and cool on a hot day and very pretty in winter. Once you cross the suspension bridge, cross over the railroad tracks and head up the trail. Stay right at the split. Usually people turn back at the end and return back the same way. There is also a stroller/wheelchair accessible path along the river as an alternative.
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Ice Glen Trail
Ice Glen Trail
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Nice easy hike. 20 mins. The glen has a windy trail that you need to scuttle through but is nice and cool on a hot day and very pretty in winter. Once you cross the suspension bridge, cross over the railroad tracks and head up the trail. Stay right at the split. Usually people turn back at the end and return back the same way. There is also a stroller/wheelchair accessible path along the river as an alternative.
Network of easy to moderate hiking trails
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Kennedy Park
275 Main St
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Network of easy to moderate hiking trails
Lake beach and walking path loop. Take your favorite floatable out on the water. A 3 minute walk from our space. The walking path (backside of the parking lot) is stroller/wheelchair accessible.
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Lake Mansfield Park
Lake Mansfield Road
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Lake beach and walking path loop. Take your favorite floatable out on the water. A 3 minute walk from our space. The walking path (backside of the parking lot) is stroller/wheelchair accessible.
Moderately challenging hike
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Race Brook Falls
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Moderately challenging hike

Arts and Culture

Classic Americana artwork by Norman Rockwell. Beautiful grounds and facilities.
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Norman Rockwell Museum
9 Glendale Rd
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Tanglewood is a very popular summer music venue. Several venues within but it’s popular to bring a picnic and sit on the large green space. Be prepared to walk a good distance. You can rent chairs there if you don’t want to carry them and there’s a variety of food options.
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Tanglewood
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Tanglewood is a very popular summer music venue. Several venues within but it’s popular to bring a picnic and sit on the large green space. Be prepared to walk a good distance. You can rent chairs there if you don’t want to carry them and there’s a variety of food options.
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Mahaiwe Performing Arts Center
14 Castle St
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Very unique industrial repurposed space. Often hosts music concerts and has a brewery, cafe, and food as well.
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MASS MoCA
1040 Mass MoCA Way
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Very unique industrial repurposed space. Often hosts music concerts and has a brewery, cafe, and food as well.
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Barrington Stage Company
30 Union St
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World class dance company. Very accessible to all. Free outdoor shows throughout the week in the summer. Get there early for a seat up close or else bring a chair of your own.
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Jacob's Pillow
358 George Carter Rd
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World class dance company. Very accessible to all. Free outdoor shows throughout the week in the summer. Get there early for a seat up close or else bring a chair of your own.
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The Mount, Edith Wharton's Home
2 Plunkett St
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Chesterwood
4 Williamsville Rd
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Sightseeing

Many great restaurants, cafes, galleries, and shops. Easily walkable.
Railroad Street
Railroad Street
Many great restaurants, cafes, galleries, and shops. Easily walkable.
Great place to visit with different exhibits throughout the year. The Fall Harvest festival is always a lot of fun.
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Berkshire Botanical Garden
5 W Stockbridge Rd
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Great place to visit with different exhibits throughout the year. The Fall Harvest festival is always a lot of fun.

Health & Wellness

Just down the street from our space on the way to town. Family friendly sessions as well.
LifeWorks Studio
50 Castle St
Just down the street from our space on the way to town. Family friendly sessions as well.
Beautiful views and hiking trails on the property.
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Kripalu Center For Yoga & Health
57 Interlaken Rd
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Beautiful views and hiking trails on the property.
A local well-regarded place for body work/massage.
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Body & Soul
184 Maple Ave
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A local well-regarded place for body work/massage.
Indoor swimming pool and warm pool. Basketball court/gym and workout facilities. Day passes available.
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Berkshire South Regional Community Center
15 Crissey Rd
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Indoor swimming pool and warm pool. Basketball court/gym and workout facilities. Day passes available.

Groceries

A local grocery with a good selection.
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Guido's Fresh Marketplace
760 S Main St
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A local grocery with a good selection.
In-town groceries and supplies
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Berkshire Food Co-op
34 Bridge St
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In-town groceries and supplies
Larger grocer with a good selection including beer/wine.
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Big Y World Class Market
10 Pleasant St
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Larger grocer with a good selection including beer/wine.
The only grocer open later night in town
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Price Chopper
300 Stockbridge Rd
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The only grocer open later night in town

Outdoor Gear

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Berkshire Bike and Board
29 State Rd
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Arcadian Shop
91 Pittsfield Rd
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Plaine's Bike Ski Snowboard
55 W Housatonic St
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