Country Retreat to The Berkshires

Advisor - Amanda Blakley

Curated By

Amanda Blakley

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  • 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.

The Fora Difference

Book with Amanda to access exclusive perks and experiences on your trip.

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

Killer perks

Free upgrades, spa credits and more—we got you

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Personalized recs

Customized travel planning for your style

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Insider knowledge

Expert advice from people who’ve actually been there

Where to stay

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Red Lion Inn

For history buffs and vintage lovers, there is no greater place to lay your weary heads than this great American inn.

Blantyre

This gorgeous Tudor revival mansion is perfect for a fabulous romantic getaway.

Fora Perks

  • ★

    $100 resort credit.

  • ★

    Breakfast daily.

  • ★

    Upgrade & extended check-in/out whenever possible.

Kemble Inn

Self-described as the height of country elegance, this refined b&b is located in one of the gilded-age mansions the area is famous for.

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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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