Art & musicSummer
Tanglewood
Lenox
Summer home of the Boston Symphony Orchestra, with concerts and picnics on the lawn.
All homes in LenoxBerkshire Guide
Let us help you have the most fun, relaxing, delicious, and memorable trip.
We've spent years exploring every corner of the Berkshires — the hidden restaurants, the trails with the best views, the galleries that stop you in your tracks. This is our curated guide to the places we love most, organized so you can plan your perfect day without the guesswork.
Start planningPlan by season
Every season has its own Berkshires
Pick a season to see what's on.
7 places
Art & musicYear-round
Norman Rockwell Museum
Stockbridge
The world's largest collection of Rockwell's original art, set on 36 acres.
All homes in StockbridgeOutdoorsSummer
Lake Garfield
Monterey
Clear water, quiet coves and some of the best sunset paddles in the county.
All homes in MontereyOutdoorsSpring – Fall
Beartown State Forest
Monterey
Miles of trails through hemlock and hardwood, with Benedict Pond at its heart.
All homes in MontereyOutdoorsWinter
Catamount & Jiminy Peak
Egremont · Hancock
Two of New England's favorite family ski mountains, minutes from our ski homes.
All homes in EgremontFood & townsYear-round
Downtown Great Barrington
Great Barrington
Farm-to-table dining, the historic Mahaiwe theater and independent shops.
All homes in Great BarringtonFood & townsYear-round
Downtown Lenox
Lenox
Walkable streets of cafés, galleries and restaurants, close to Tanglewood.
All homes in LenoxThe Berkshires. Come see for yourself.
Want personal recommendations for your dates? Our local team is happy to help plan your trip.