Arts & Culture
Tanglewood
The famous music venue is near by.
Jacob's Pillow
358 George Carter RdThe famous dance center is near by.
Great live broadcasts of theatre, music and dance from around the world. Live music events. Lectures. All sorts of great stuff. Check out their website for the latest:
www.mahaiwe.org/
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Mahaiwe Performing Arts Center
14 Castle StGreat live broadcasts of theatre, music and dance from around the world. Live music events. Lectures. All sorts of great stuff. Check out their website for the latest:
www.mahaiwe.org/
A wonderful local theatre company showcasing both new and classic works by some of the nation's top writers and directors.
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Barrington Stage Company
30 Union StA wonderful local theatre company showcasing both new and classic works by some of the nation's top writers and directors.
The museum dedicated to all things Norman Rockwell in Stockbridge, MA - a beautiful old town with lots of shopping and dining options.
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Mużew Norman Rockwell
9 Glendale RdThe museum dedicated to all things Norman Rockwell in Stockbridge, MA - a beautiful old town with lots of shopping and dining options.
The home of author Edith Wharton is now a museum and cultural institution offering garden and house tours, a literary circle, and ghost tours on Friday nights.
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The Mount, Dar Edith Wharton
2 Plunkett StThe home of author Edith Wharton is now a museum and cultural institution offering garden and house tours, a literary circle, and ghost tours on Friday nights.
Summer stock theatre located in Sharon, CT - a 35 minute drive from Skylight.
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Sharon Playhouse
49 Amenia RdSummer stock theatre located in Sharon, CT - a 35 minute drive from Skylight.
Food Scene
Historic Inn & Restaurant. Recently under new management. A Fine Dining experience.
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The White Hart
15 Under Mountain RdHistoric Inn & Restaurant. Recently under new management. A Fine Dining experience.
Lovely laid back of the moment atmosphere. A good choice for a romantic meal. Delicious food and great service. Beautiful fields to look out on while you eat.
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Cantina 229
229 Hartsville-New Marlborough RdLovely laid back of the moment atmosphere. A good choice for a romantic meal. Delicious food and great service. Beautiful fields to look out on while you eat.
Another historic Inn. With several Intimate small dining rooms, each unique in character, offering delicious comfort food.
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The Old Inn On The Green
Another historic Inn. With several Intimate small dining rooms, each unique in character, offering delicious comfort food.
A local favorite. Unique farm to table dishes. A real farm that has been converted into a B&B and restaurant and event space.
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Gedney Farm
34 Hartsville-New Marlborough RdA local favorite. Unique farm to table dishes. A real farm that has been converted into a B&B and restaurant and event space.
A fun place to hang out in the village of Southfield for a casual brunch or lunch. A cafe/restaurant with delicious fresh baked goods and bread. Also great desserts, ice cream and of course Coffee.
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The Southfield Store
163 Norfolk RdA fun place to hang out in the village of Southfield for a casual brunch or lunch. A cafe/restaurant with delicious fresh baked goods and bread. Also great desserts, ice cream and of course Coffee.
A famous Inn and Restaurant in nearby Stockbridge. A local and tourist favorite for decades in this area.
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The Red Lion Inn
30 Main StA famous Inn and Restaurant in nearby Stockbridge. A local and tourist favorite for decades in this area.
Great coffee, baked goods, and healthy but yummy lunch menu at a good price. A good place to sit with your computer and take in the local color of nearby Great Barrington, MA
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Fuel Bistro/ Coffee Shop
293 Main StGreat coffee, baked goods, and healthy but yummy lunch menu at a good price. A good place to sit with your computer and take in the local color of nearby Great Barrington, MA
Great Mexican food at a good price. Right near the movie theatre in Great Barrington, MA.
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Fiesta Bar and Grill
284 Main StreetGreat Mexican food at a good price. Right near the movie theatre in Great Barrington, MA.
Great Brunch & Lunch menu. Good quick service. Hearty delicious food.
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GB Eats
282 Main StGreat Brunch & Lunch menu. Good quick service. Hearty delicious food.
This local Farmer's Market is still open during the summer and early fall on Saturdays from 9-1. Great produce, baked goods, organic meat, and a casual outdoor brunch spot.
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Great Barrington Town Hall
Church StreetThis local Farmer's Market is still open during the summer and early fall on Saturdays from 9-1. Great produce, baked goods, organic meat, and a casual outdoor brunch spot.
A great place to get fresh baked sweets or stop for brunch or lunch in nearby Canaan, CT. Across from Stop & Shop on Main Street.
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Blackberry River Baking Co
18 E Main StA great place to get fresh baked sweets or stop for brunch or lunch in nearby Canaan, CT. Across from Stop & Shop on Main Street.
A historic diner located next to the railroad tracks on Main St. in Canaan, Ct. Great for a quick and easy breakfast or lunch in a vintage setting.
Collin's Diner
53 Main StA historic diner located next to the railroad tracks on Main St. in Canaan, Ct. Great for a quick and easy breakfast or lunch in a vintage setting.
Sheffield Farmers' Market
125 S Main StGreat farmer's market on Friday afternoons from 3-6pm.
Stateline Pizza
340 N Elm StGreat pizza and casual Italian and American food.
Parks & Nature
This magical place is minutes from the house by car, and about 15 minute hike on foot to get there. A truly beautiful waterfall. Serene and exciting at the same time. Great for hiking in during the summer. Or for watching the water run through the ice in the winter. They have places to bbQ and picnic as well.
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Umpachene Falls Park
Umpachene Falls RoadThis magical place is minutes from the house by car, and about 15 minute hike on foot to get there. A truly beautiful waterfall. Serene and exciting at the same time. Great for hiking in during the summer. Or for watching the water run through the ice in the winter. They have places to bbQ and picnic as well.
Campbell Falls State Park
Spaulding RoadMonument Mountain Reservation
Bartholomew's Cobble Reservation
105 Weatogue RdWonderful hiking
Bear Mountain
Park tal-Bash Bish Falls
Falls RoadHaystack Mountain State Park
Connecticut 272Wonderful hiking all year round. And swimming in the summer.
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York Lake
Wonderful hiking all year round. And swimming in the summer.
Entertainment & Activities
A fun retro bowling alley with a small arcade and a bar. Also a funky indoor miniature golf course.
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Cove Bowling Lanes
109 Stockbridge RdA fun retro bowling alley with a small arcade and a bar. Also a funky indoor miniature golf course.
About a 20 minute drive from the house and near lots of great restaurants and shops in downtown Great Barrington.
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The Triplex Cinema
70 Railroad StAbout a 20 minute drive from the house and near lots of great restaurants and shops in downtown Great Barrington.
Butternut is a 15 minute drive from Skylight. They offer skiing, boarding and tubing during the winter months. And a leaf-peeper gondola ride in the fall. Rope and zip line courses are open during the summer.
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Butternut Basin
Butternut is a 15 minute drive from Skylight. They offer skiing, boarding and tubing during the winter months. And a leaf-peeper gondola ride in the fall. Rope and zip line courses are open during the summer.
This community center in Great Barrington has an indoor pool where you can swim for a small fee. Great for people who like to swim during the cooler months of the year.
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Berkshire South Regional Community Center
15 Crissey RdThis community center in Great Barrington has an indoor pool where you can swim for a small fee. Great for people who like to swim during the cooler months of the year.
Essentials
Big Y World Class Market
10 Pleasant StPrice Chopper
300 Stockbridge RdStop & Shop
55 Village Green DrGood donuts on weekend mornings. As well as several area papers are available. Good for basics like milk, juice, etc. Also stocks specialty ice cream and a decent selection of wine.
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Mill River General Store
10 Great Barrington RdGood donuts on weekend mornings. As well as several area papers are available. Good for basics like milk, juice, etc. Also stocks specialty ice cream and a decent selection of wine.
A specialty grocery store. Lots of special edible goodies for your special visit to the Berkshires.
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Guido's Fresh Marketplace
760 S Main StA specialty grocery store. Lots of special edible goodies for your special visit to the Berkshires.
Everything Else
A nationally known center for wellness and R&R. Offers a wide variety of workshops on various topics related to yoga and self-care. Also offers massage and bodywork.
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Kripalu Center For Yoga & Health
57 Interlaken RdA nationally known center for wellness and R&R. Offers a wide variety of workshops on various topics related to yoga and self-care. Also offers massage and bodywork.
Offers yoga classes for all levels in nearby Great Barrington.
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Yoga Great Barrington
30 Elm CtOffers yoga classes for all levels in nearby Great Barrington.
Shopping
Awesome independent bookstore with both bestsellers and small press alike. In a small mall on Stockbridge Road in Great Barrington, right next to Price Chopper and Kmart.
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The Bookloft
63 State RdAwesome independent bookstore with both bestsellers and small press alike. In a small mall on Stockbridge Road in Great Barrington, right next to Price Chopper and Kmart.
Main Street and Railroad street in Great Barrington have a wide variety of shops and restaurants. Fun to walk and browse, stop for a bite, etc.
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Main Street
317 Main StMain Street and Railroad street in Great Barrington have a wide variety of shops and restaurants. Fun to walk and browse, stop for a bite, etc.