Sightseeing
Picturesque river with amazing trails to hike, bike or 4-wheel on.
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Chesterfield Gorge Reservation
Picturesque river with amazing trails to hike, bike or 4-wheel on.
Annual fair at the end of August that is over 125 years old! Old time country fair that features 4-H animal events, concerts and demolition derby.
Cummington Fair
97 Fairgrounds RdAnnual fair at the end of August that is over 125 years old! Old time country fair that features 4-H animal events, concerts and demolition derby.
Stop by for penny candy, ice cream, baked goods and small gifts including earrings, incense, kitchen & bath items, as well as a nice kids' department with toys, crafts and books.
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Williamsburg General Store
12 Main StStop by for penny candy, ice cream, baked goods and small gifts including earrings, incense, kitchen & bath items, as well as a nice kids' department with toys, crafts and books.
William Cullen Bryant Homestead
207 Bryant RdGreat place on a rainy day. Park in the garage out back, and walk right into Thornes Marketplace. A cute mix of boutique shops & restaurants.
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Thornes Marketplace
150 Main StGreat place on a rainy day. Park in the garage out back, and walk right into Thornes Marketplace. A cute mix of boutique shops & restaurants.
Great collection of books, and a fun place to spend an hour or two.
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The Bookstore and Get Lit Wine Bar
11 Housatonic StGreat collection of books, and a fun place to spend an hour or two.
Grab a table on the front porch and spend a few hours enjoying the views of Stockbridge village center.
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The Red Lion Inn
30 Main StGrab a table on the front porch and spend a few hours enjoying the views of Stockbridge village center.
Kripalu Center For Yoga & Health
57 Interlaken RdVisit MASS MoCA for an afternoon and get blown away by some of the most amazing comtemporary art. Bookstore and cafe on-site.
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MASS MoCA
1040 Mass MoCA WayVisit MASS MoCA for an afternoon and get blown away by some of the most amazing comtemporary art. Bookstore and cafe on-site.
Academy of Music Theatre
274 Main StHistoric music venue and theater in Northampton.
Spare Time Northampton
525 Pleasant StClassic bowling alley in Northampton
Lee Premium Outlets
17 Premium Outlet BoulevardNorman Rockwell Museum
9 Glendale RdThe Baker's Pin
34 Bridge StGourmet cooking store in Northampton, that also offers cooking classes.
WEBS - America's Yarn Store
75 Service Center RdYarn superstore in Northampton.
Yankee Candle
25 Greenfield RdMagic Wings Schmetterlingskonservatorium
281 Greenfield RdJacob's Pillow
358 George Carter RdTanglewood
Look Park in Northampton has a spray park, playground, train, pedal boats, tennis and mini-golf. Great place for families with young kids.
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Look Denkmalpark
300 N Main StLook Park in Northampton has a spray park, playground, train, pedal boats, tennis and mini-golf. Great place for families with young kids.
The Parlor Room
32 Masonic StSmall, music venue in downtown Northampton.
Mount Greylock
Hancock Shaker Village
1843 W Housatonic StThe Clark Art Institute
225 South StBerkshire East Mountain Resort
66 Thunder Mountain RdFood scene
Great place for coffee, bagels, sandwiches and a large dose of local flavor.
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Old Creamery Co-op
445 Berkshire TrailGreat place for coffee, bagels, sandwiches and a large dose of local flavor.
Chesterfield General Store
432 Main RdLocal wood-fired pizza and general store.
Long time Northampton vegetarian restaurant. Early pioneers of the clean food movement.
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Paul and Elizabeth's
150 Main StLong time Northampton vegetarian restaurant. Early pioneers of the clean food movement.
Guido's Fresh Marketplace
760 S Main StA great local organic marketplace in Pittsfield.
Delicious croissants that rival something you'd find in New York or Paris.
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Bread Euphoria
206 Main StDelicious croissants that rival something you'd find in New York or Paris.
Great local food coop, for organic foods and vegetables. Meats, prepared foods, lots of unique products! You do not have to be a coop member to shop here.
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River Valley Co-op
330 N King StGreat local food coop, for organic foods and vegetables. Meats, prepared foods, lots of unique products! You do not have to be a coop member to shop here.
Tandem Bagel Company
9 Railroad StGreat local bagel shop with sandwiches and smoothies.
One of the many local breweries that have popped up in the Hilltowns over the past decade.
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Fort Hill Brewery
30 Fort Hill RdOne of the many local breweries that have popped up in the Hilltowns over the past decade.
A great cafe and eatery in Northampton that is loved by locals.
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Woodstar Cafe
60 Masonic StA great cafe and eatery in Northampton that is loved by locals.
One of the amazing apple orchards that you can visit to pick your own, or stop by the store for a bag of delicious Honey Crisp apples, cider donuts and other fall favorites.
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Pine Hill Orchard
248 Greenfield RdOne of the amazing apple orchards that you can visit to pick your own, or stop by the store for a bag of delicious Honey Crisp apples, cider donuts and other fall favorites.
Quonquont Farm offers blueberries, peaches and apples throughout the summer and fall months.
Quonquont Farm
9 North StQuonquont Farm offers blueberries, peaches and apples throughout the summer and fall months.
Bistro Zinc
56 Church StGreat place for lunch or dinner when in Lenox.
Herrell's Ice Cream & Bakery
8 Old S StLocal favorite in Northampton for icecream.
Spoleto is open for happy hour & dinner, and has a great outdoor patio & bar. Plus, convenient parking behind the restaurant!
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Spoleto
1 Bridge StSpoleto is open for happy hour & dinner, and has a great outdoor patio & bar. Plus, convenient parking behind the restaurant!
Busy seasonal, outdoor dining spot in Williamsburg! After your food, you can walk next door to get an ice cream!
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Local Burgy
93 Main StBusy seasonal, outdoor dining spot in Williamsburg! After your food, you can walk next door to get an ice cream!
Bascom Lodge
3 N Adams RdCool local brewery and restaurant with pour room & outdoor beer garden.
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Tree House Brewing Company - Deerfield
1 Community PlaceCool local brewery and restaurant with pour room & outdoor beer garden.
Listons Bar & Grill
324 Old North Rd