The Heart and the Art of The Berkshires
Pittsfield & Lenox, MA
Sat. Nov 22 - Sun. Nov 23, 2025
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This swath of low mountains in western Massachusetts has been home to writers, artists and artisans working at the absolute peak of their powers.
Escape to Pittsfield and Lenox for a sampling of the natural beauty and creative energy that runs through these hills.
Your stay, dinner, and curated local experience. Bookable in one click.
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—> 3 hours from NYC
—> 2½ hours from Boston
Why here?
“A very paradise of painters,” said Herman Melville of the the Berkshire high hills ringing his home in Pittsfield. “The circle of the stars cut by the circle of the mountains.”
The Berkshires, a range of modest mountains in Western Massachusetts, have produced a disproportionate of amount of vision and artistry.
Moby Dick was born here; the civil rights pioneer W.E.B Du Bois was raised here; Nathaniel Hawthorne and Edith Wharton wrote some of their best-known works here; an enslaved woman named Elizabeth Freeman sued the state of Massachusetts for her freedom and won here; Norman Rockwell painted its shopkeepers and storefronts here; Stephen Sondheim wrote his first musicals in college here; Leonard Bernstein and countless others made it their musical home in summertime. All of it happened in the Berkshires.
None of that is to mention the beauty of the place. The mountains (by Massachusetts standards ) roll and merge together, more towering-feeling than their altitudes give them right to seem, with villages and mills and curling rivers plunked between them.
In the Berkshires, you can walk the surrounding fields of Melville’s home, and take in the same same little-changed circle of mountains he wrote of 175 years ago. And be part of a place that has contributed to the world much more than its fair share of art, beauty and history.
This weekend in the Berkshires, discover…
The stay.
Hotel on North
Nestled nicely into quaintness of downtown Pittsfield, at something close to the exact geographic center of this region, Hotel on North is an ideal home base no matter where your Berkshirian wanders take you.
The property is spread over a pair of historic 19th century buildings, with meticulously preserved features: spans of exposed brick, tin ceilings (an Ovenrightist favorite, always) and eclectic design features; all restored beautifully.
It’s a terrific rendering of Pittsfield’s past, blended with glimpses of its future.
Arrowhead
If there is one ironclad must-do in in the Berkshires (and, respectfully, we will not be hearing arguments) it’s Herman Melville’s Arrowhead: the homeplace, backdrop, and frequent inspiration of Herman Melville’s most enduring work as a writer.
This modest-looking yellow farmhouse is a marvel of literary history; and it feels that way as you step through the transom. It was the birthplace of Moby Dick, written in Melville’s second-floor writing studio.
A guided tour of Arrowhead is included here. It features a spin through the writing room, where you can stare off at Mt. Greylock, the hump-like mountain that reminded Melville of a whale.
The day.
The find.
An American Craftsman
A fixture in nearby Lenox (where, incidentally Melville’s friend Nathaniel Hawthorne also lived and wrote for a time), An American Craftsman curates a wonderful collection of handmade, artful items, from glass and metal to jewelry and apparel.
The food.
Cello
Threads of artistry and memory also run through the culinary scene in the Berkshires.
”We find great fulfillment in knowing that we’re contributing to the memories our guests will carry with them about their meals,” say the creators of Cello, an intimate, 29-seat restaurant in Lenox.
It has a locally-sourced seasonal menu, changing day to day with availability, and a lunch-counter style bar looking into an open kitchen.
”[W]e get ingredients when they’re truly at their peak, and that translates to fresher flavor, better texture, and a deeper connection to what we’re serving,” the executive chef and general manager partners say. “It creates this wonderful rhythm for the menu, because what’s available changes with the seasons.”
Edith Wharton’s Library
Not to make this itinerary all writers all the time, but yet another of America’s greatest writers, Edith Wharton (author of Ethan Frome and The Age of Innocence) lived and worked in these hills.
At The Mount, her grand estate in Lenox, a well-preserved library of 2,700 volumes remains. The books include incredible marginalia and notes in Wharton’s hand, and taken together, the space is a wood-paneled portal into Wharton’s time and her broad constellation of influences.
The tucked away.
Nightwood, The Mount
After your library-stop, hang around The Mount for the fantastical Nightwood, a theatrical light and music exhibition staged after sundown in the extensive gardens of the estate. It only happens a handful of dates in November, and you’ll be there for one of them on Saturday night.
Drinks and food are served at the Nightwood Café in the courtyard, and there’s a bookstore too.
The evening mood.
One-night stay for one or two at Pittsfield’s Hotel on North. Sat. Nov 22, 2025.
Pre-paid dinner at Cello in nearby Lenox, You have reservations at 6:30pm on Saturday evening.
Guided tour of Herman Melville’s Arrowhead. Saturday morning, 11am.
You’ll receive a detailed itinerary after booking confirmation.
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