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.
398 locals recommend
Tanglewood
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.
257 locals recommend
Jacob's Pillow
358 George Carter RdIncredible outdoor venue for all types of dance performances all summer.
Naumkeag
5 Prospect Hill RdLovely 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.
21 locals recommend
Pontoosuc Lake
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.
14 locals recommend
Lake Garfield
A lake just a few minutes away with a small beach, swimming area, and launch for kayaks and boats.
Apple Tree Inn
10 Richmond Mountain RoadCute hotel near Tanglewood with great live music in an enchanted feeling old bar
The Barn
17 Main StExcellent live music venue with outdoor seating and good casual food
Lion's Den
30 Main StLive 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.
46 locals recommend
Cantina 229
229 Hartsville-New Marlborough RdIncredible 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.
72 locals recommend
The Old Inn On The Green
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.
44 locals recommend
The Southfield Store
163 Norfolk RdBest deli nearby, with a fantastic Sunday breakfast and just excellent vibes all week long.
Guido's Fresh Marketplace
760 S Main StBest grocery store; lovely organic and local options
Perfect spot to pick up wine, cheese, charcuterie, and everything else you need for a Berkshires picnic.
52 locals recommend
Rubiner's Cheesemongers
264 Main StPerfect 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
203 locals recommend
The Prairie Whale
178 Main StDelicious, 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.
7 locals recommend
Rawson Brook Farm
185 New Marlboro RdJust a little walk down the road; see the goats and pick up some incredible goat's cheese at the farmstand.
Brava
65 Church StWine bar, small plates, great late night energy.
The Red Lion Inn
30 Main StClassic 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.
188 locals recommend
Great Barrington
Perfect little town where we pick up groceries and often go out to eat. Farmers market on Saturday mornings.
Lenox
Cute town with lovely restaurants, art galleries, and parks.
About an hour away, incredible restaurants, furniture and vintage stores, bars, etc. etc.
442 locals recommend
Hudson
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
69 locals recommend
Stockbridge
Adorable historic old New England town to walk around and grab an ice cream or coffee