The Berkshires Guide


The Berkshires, simply put, is special. Located about 2 1/2 hours from Boston or New York it offers a place of history, nature, and cultural attractions. No wonder it has served as an epicenter for artists, musicians, and authors for over a century. People such as Edith Wharton, Nathaniel Hawthorne, Herman Melville, and Daniel Chester French all found themselves at different times in the Berkshires, and the tradition continues to this day of cultural movers and shakers passing through this famous region.

When I meet people who have visited the Berkshires, their eyes instantly take on a euphoric glaze recalling those special memories in a place that is unlike any other. It has such personal meaning for me because it is also the summer home of the Boston Symphony Orchestra, where my father was a member and where we spent all our summers. My best memories are in the Berkshires so it was a sentimental trip to return after 10 years, and I felt happily relieved that not too much had changed and I got to see the profound beauty the area has to offer with more experienced adult eyes.

There is no excuse for boredom with so many things to explore and discover and yet one can also just quietly immerse themselves in the mountain views and gorgeous countryside. That’s what makes it so great - the Berkshires can be whatever you want it to be.



Rubi’s Cafe | A cheese shop and cafe, this is one of my favorite places in the area. The grilled cheese menu is like no other, but I always order their Cubano sandwich. It is also a good place to stop in for an afternoon coffee and pastry. Make sure to duck into their cheese shop for some gourmet goodies to-go. | Great Barrington, MA

Brava Wine Bar & Restaurant | A casual bar with tasty bites and craft beer. Try the Garlic Shrimp or one of their handmade pizzas. | Stockbridge, MA

Ben Gable Savories | This cute little lunch spot has scrumptious buttery quiches, savory pastries, and local ingredient salads. | Chatham, NY

Botanica | A new addition to Great Barrington, a great place for a quick taco lunch or a happy hour craft cocktail at their beautifully stocked bar. | Great Barrington, MA

Bartlett’s Orchards | A must stop for a freshly made apple cider donut, homemade pie, or hand pressed bottle of apple cider. It also has seasonal farm fruits and vegetables, as well as jams, vinegars, and chutneys, all available to purchase. | Richmond, MA

Other options: Allium, Baba Louie, Nudel, The Praire Whale, Guido’s Fresh Market Place, The Six Depot, & Bistro Box


Hammertown | A great home store filled with new and vintage finds. It has furniture, linens, candles, coffee table books, kitchen items, and antiques. | Great Barrington, MA

One Mercantile | A curated gift shop with a selection of artisanal good gifts including locally made products. | Great Barrington, MA

Twigs | This clothing store has a great selection of denim, as well as an impressive choice of designer pieces from The Great, Ulla Johnson, and Nili Lotan. | Great Barrington, MA

Baldwin’s Extracts | Established in 1888 by Charles Baldwin, the store sells their famous vanilla extract, along with other flavors, as well as their own maple syrup, rose water, aftershaves, retro candies and toys. | West Stockbridge, MA


The Mount | The Berkshire Estate of Edith Wharton is worth visiting for its beautiful gardens and grounds. Edith Wharton was a pioneer of her time and the first woman to win a Pulitzer Prize. | Lenox, MA

Chesterwood | The home and studio of American sculptor Daniel Chester French. He has created many well known pieces most notably the Lincoln Memorial in Washington D.C. and the Minute Man in Concord, MA. This is one of my favorites places to recommend for people to visit in the Berkshires. | Stockbridge, MA

Tanglewood | The summer home of the Boston Symphony Orchestra. It is an absolute must to take a picnic to a concert at Tanglewood for a quintessential Berkshires evening under the stars. A place so close to my heart, I spent my entire childhood running on the lawns of Tanglewood listening to the orchestra rehearse. Frequent guest performers are James Taylor, Conductor John Williams, and Yo Yo Ma. | Lenox, MA

Jacob’s Pillow | The dance center and school is considered the oldest acclaimed summer dance festival in the US. Go see a live performance in one of the theaters or watch one of their free outdoor performances offered on certain nights.

The Clark Art Institute | The Sterling and Francine Clark Art Institute is an art museum and research center located on 140-acre campus. It has many beautiful and important works and is especially known for the French Impressionist works of Renoir, Monet, Degas, and the American painter John Singer Sargent.

Other: Shakespeare & Company, Hike at Bash Bish Falls, Hancock Shaker Village


The Inn at Kenmore Hall | Frank Mjuytens and Scott Edward Cole have brought to life an 18th-Century house and reimagined it into the idyllic New England home it is today. Newly opened, every corner of the house looks as though it has always been that way and is layered with midcentury furniture, antiques, pieces of art, and seasonal flowers. Their handsome resident dog Dutch oversees it all. The attention to detail is something you will not find elsewhere, with the most comfortable rooms and impeccable bathrooms, and a delicious daily breakfast with the best coffee. (see the incredible spread of seasonal quiche, smoked salmon, pastries, yogurt and granola, and fruit below.) This charming bed-and-breakfast will be filling up fast once the word is out. I am already looking forward to returning next year!

Hotel on North | A modern boutique hotel with a casual restaurant located in the heart of Pittsfield. | Pittsfield, MA

Wheatleigh | A splurge-worthy hotel located on 22 acres of land surrounded by trees and mountains. It’s worth stopping in for a glass of champagne to take in the surroundings or go for a bite in one of their acclaimed restaurants.

Blantyre | A Tudor style style house built in 1902, it has recently undergone renovations to the 110-acre property. It also offers a spa, casual bistro, and fine dining restaurant.

Other options : AirBNB