When James Taylor called the Berkshires “dreamlike,” he was certainly onto something. Nestled between the mountain ranges and rolling hills of Connecticut and Massachusetts, it’s served as a worthy mountain escape for East Coasters seeking a getaway from the hum drum of the city for more than a century.


The newest destination in the Inspirato portfolio, the Berkshires is home to Woodland Estate, a stunning, gated five-bedroom lodge set on 72 gated acres of unspoiled beauty. We’ve compiled four of our favorite must-do activities for Inspirato members staying at the estate during their vacation in this postcard-worthy stretch of Massachusetts. We hope it inspires you to begin planning your own Berkshires getaway.

Visit the Clark Art Institute


A small-town art museum with a big-city collection, the Clark houses Impressionist masterpieces from heavy hitters like Renoir, Degas, and Rodin, as well as a collection of 18th-century furniture and fine porcelain. City slickers missing the Met and MoMA won’t be disappointed in the showings.

(Fun fact: The Clark is one of the few places in the world with distinction as both an art museum and a center of higher education, with undergraduate and graduate programs available.)

Catch a show at Tanglewood Music Festival


If you’re visiting in July and August, Tanglewood is a must. The Berkshires’ premier outdoor summer concert series, a tradition since 1936, first began when the Boston Symphony Orchestra first performed here. The festival’s acts are typically a mix of classical musicians and folk singers.

(Fun fact: Tanglewood’s 2021 lineup includes some big names, including Ringo Starr, John Legend, and Brandi Carlile.)

Hike Mount Greylock State Reservation


This picturesque state park is a worthy spot to earn your bragging rights. Hike a section of the Appalachian Trail or go all the way up to the summit of Mount Greylock, the highest peak in Massachusetts at 3,491 feet. You can see up to 90 miles of New England’s idyllic beauty from its peak.

(Fun fact: Mount Greylock is also visible from Woodland Estate.)

Ski Jiminy Peak Mountain Resort


Massachusetts’ premier ski destination, Jiminy Peak is the largest resort in Southern New England. It’s also a great pick for families and beginners. Find fresh powder on its 45 runs and trails, or embrace the evening with a twilight run—the slopes are open till 9:30 p.m.

(Fun fact: During the summer, it also doubles as a mountain adventure park, featuring alpine slides, scenic chairlift rides, a rock wall, mountain biking trails, and more.)

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