Country Retreat to The Berkshires

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Advisor - Amanda Blakley
Curated By

Amanda Blakley

  • USA

  • Massachusetts

  • Arts & Culture

  • Domestic Travel

  • Family Travel

  • Slow Travel

  • Countryside

  • Fall

  • Old-fashioned

berkshires massachusetts tall tree with orange and green leaves on branches and ground and a tan house in the background
Curator’s statement

A country retreat for city folk with a history dating back to the early 1800s, you might call her old-fashioned – but there is nothing stodgy about the beautiful Berkshires. You’ll find elegant homesteads and gilded-age mansions, gardens aplenty, picturesque Americana towns, antique shops and a food trail to rival any farm-to-table culinary destination.

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Where to stay

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Things to do

stack of five golden pancakes with blueberries and maple syrup on a blue plate and wooden platter orange juice in clear glass

Culture & history

Spend an evening channeling the life and times of Edith Warton at The Mount & Gardens, her beloved country estate. Fridays and Saturdays throughout the summer offer live music and jazz, while fall is a great time to take a ghost tour of the home and property.

Tour the gilded age mansion and gardens of Naumkeag. If you happen to visit over a Thursday evening, stay for the live music and food.

A visit to Stockbridge isn’t complete without spending time in the history-filled halls of the Norman Rockwell Museum. Norman lived and painted for much of his life in this community and the largest representation of his work can be found lining the walls. Kids will appreciate the paintings of children their own age.

Live music

Jacob's Pillow is an iconic dance festival and historic landmark nestled in the Berkshires, with performances running all summer. They showcase a wide range of dance companies and styles. A must-do!

If Tanglewood is in season (June through August), be sure to catch a matinee at Seranak Cottage, the summer home of the Boston Symphony Orchestra since the 1930s. You can order a picnic online via their website, or head to Ne Jaime's Wine Cellars in Stockbridge for the best in gourmet fare – pre-packaged picnics or self-curated. They'll even pack your wine or beer on ice and provide serviettes and silverware.

Shopping downtown

Head to Great Barrington to poke around the sweet shops that line Main Street. One Mercantile for copper mint julep mugs, ceramics and salt water taffy, Rubiner's Cheese Mongers & Grocers for some funky fromage and of course, Tom's Toys.

Advisor - Amanda Blakley

A note from Amanda

Consider planning a visit around the Tanglewood and Jacob’s Pillow. If you’re into cool old things, you could coordinate your stay with the Brimfield Flea Market. Summer is generally the best time to visit.

Advisor - Amanda Blakley

Travel Advisor

Amanda Blakley

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