Our favorite Berkshires spots

Susan
Our favorite Berkshires spots

To do

Live music and the Boston Symphony's home for the summer. Bring a picnic and enjoy a classic Berkshires night under the stars.
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Tanglewood
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Live music and the Boston Symphony's home for the summer. Bring a picnic and enjoy a classic Berkshires night under the stars.
Incredible outdoor venue for all types of dance performances all summer.
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Jacob's Pillow
358 George Carter Rd
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Incredible outdoor venue for all types of dance performances all summer.
Lovely old estate for events and a nice picnic spot
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Naumkeag
5 Prospect Hill Rd
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Lovely old estate for events and a nice picnic spot
We often rent pontoon boats here with friends on sunny days. Reserve in advance. U-Drive Boat Rentals.
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Pontoosuc Lake
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We often rent pontoon boats here with friends on sunny days. Reserve in advance. U-Drive Boat Rentals.
A lake just a few minutes away with a small beach, swimming area, and launch for kayaks and boats.
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Lake Garfield
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A lake just a few minutes away with a small beach, swimming area, and launch for kayaks and boats.
Cute hotel near Tanglewood with great live music in an enchanted feeling old bar
Apple Tree Inn
10 Richmond Mountain Road
Cute hotel near Tanglewood with great live music in an enchanted feeling old bar
Excellent live music venue with outdoor seating and good casual food
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The Barn
17 Main St
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Excellent live music venue with outdoor seating and good casual food
Live music in a historic old bar
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Lion's Den
30 Main St
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Live music in a historic old bar

Food scene

Incredible food, with several different formats depending on the day of the week. We can't recommend taco night on Mondays and Tuesdays enough.
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Cantina 229
229 Hartsville-New Marlborough Rd
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Incredible food, with several different formats depending on the day of the week. We can't recommend taco night on Mondays and Tuesdays enough.
Fantastic dinner in a lovely old inn. Perfect for a celebration.
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The Old Inn On The Green
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Fantastic dinner in a lovely old inn. Perfect for a celebration.
Best deli nearby, with a fantastic Sunday breakfast and just excellent vibes all week long.
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The Southfield Store
163 Norfolk Rd
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Best deli nearby, with a fantastic Sunday breakfast and just excellent vibes all week long.
Best grocery store; lovely organic and local options
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Guido's Fresh Marketplace
760 S Main St
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Best grocery store; lovely organic and local options
Perfect spot to pick up wine, cheese, charcuterie, and everything else you need for a Berkshires picnic.
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Rubiner's Cheesemongers
264 Main St
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Perfect spot to pick up wine, cheese, charcuterie, and everything else you need for a Berkshires picnic.
Delicious, lively, farm to table restaurant in Great Barrington
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The Prairie Whale
178 Main St
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Delicious, lively, farm to table restaurant in Great Barrington
Just a little walk down the road; see the goats and pick up some incredible goat's cheese at the farmstand.
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Rawson Brook Farm
185 New Marlboro Rd
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Just a little walk down the road; see the goats and pick up some incredible goat's cheese at the farmstand.
Wine bar, small plates, great late night energy.
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Brava
65 Church St
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Wine bar, small plates, great late night energy.
Classic hotel, nice food, lovely space
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The Red Lion Inn
30 Main St
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Classic hotel, nice food, lovely space

City/town information

Perfect little town where we pick up groceries and often go out to eat. Farmers market on Saturday mornings.
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Great Barrington
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Perfect little town where we pick up groceries and often go out to eat. Farmers market on Saturday mornings.
Cute town with lovely restaurants, art galleries, and parks.
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Lenox
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Cute town with lovely restaurants, art galleries, and parks.
About an hour away, incredible restaurants, furniture and vintage stores, bars, etc. etc.
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Hudson
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About an hour away, incredible restaurants, furniture and vintage stores, bars, etc. etc.
Adorable historic old New England town to walk around and grab an ice cream or coffee
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Stockbridge
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Adorable historic old New England town to walk around and grab an ice cream or coffee