Even Litchfield County, Conn., once home to farm stands and little else, is full of cashed-up city slickers.
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County → cash → slickers
That leaves the Berkshires.
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That → leave → Berkshires
Three hours from Manhattan, this western Massachusetts mountain range has somehow avoided becoming completely unattainable for the regular Joe.
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range → avoid → Joe
You can still book a charming inn, take the kids to dinner and expand your cultural horizons without dipping into the 401(k) — especially if you visit now.
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you → book → 401(k
In the late 19th century, the Berkshires were the Newport of the mountains — a summer refuge for the same Gilded Age families who built mansions on Bellevue Avenue.
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who → build → Avenue
The Vanderbilts and the Carnegies erected sprawling cottages across Lenox and Stockbridge.
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Vanderbilts → erect → Lenox
Edith Wharton wrote “The House of Mirth” at the Mount.
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Wharton → write → Mount
Old-money DNA is everywhere in the Berkshires, but the price of admission today has almost nothing to do with what it cost back then.
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it → have → what
“While summer rates can be higher, our efforts focus on expanding the Berkshires into a year-round destination, offering lower prices in off-peak seasons,” said Lindsay Schmid, senior vice president of the region’s tourism board.
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Schmid → focus → board
“We are actively working to make the region more accessible to underserved, younger, less affluent and more diverse travelers.
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region → work → travelers
In other words: Strike now, while the rates are still within reach.
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rates → strike → reach
Where to stay
For something between a hotel and camping, there is Huttopia Berkshires (from $83), where you can stay in a spacious tent or tiny house and have easy access to mountain biking at Jiminy Peak, as well as hiking on nearby Mount Greylock.
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you → stay → Greylock
In Lenox, Brook Farm Inn (from $194) is the sort of old-fashioned bed-and-breakfast that people crave in New England, complete with fireplaces, four-poster beds and a hearty homemade breakfast included in your rate.
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people → crave → rate
And for something that feels like a splurge but really isn’t, the Williams Inn (from $181) in the heart of vibrant Williamstown offers a boutique hotel experience with front-row access to nearby attractions, including the Clark Art Institute, Mass MoCA and the Williamstown Theatre Festival.
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Inn → feel → Institute
Where to eat
The Berkshires’ dining scene spans everywhere from seasonal New England fare to internationally influenced fine dining.
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scene → eat → dining
Check out State Food and Drink, a rotating restaurant that serves farm-to-table fare on weekends, Southern food on Mondays and Vietnamese food on Tuesdays.
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that → check → Tuesdays
It’s unfussy and inventive.
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It → ’ → ?
The same could be said of Berkshire Mountain Bakery, a Housatonic institution known for its wood-fired sourdough.
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same → say → sourdough
Wherever you go, dinnertime feels like an authentic local event here, especially in North Adams at Casita, which interprets Mexican fare through the lens of Berkshires seasonality.
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which → go → seasonality
It’s proof that the Berkshires’ dining scene has caught up to its scenery, even if the prices haven’t caught up to the Hamptons.
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prices → ’ → Hamptons
What to do
Each October, when the foliage turns, the Halloween spirit becomes palpable.
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spirit → turn → What
Check out the Mount, Edith Wharton’s former estate in Lenox, which runs ghost tours this time of year that lean into the house’s eerie history (Fridays at 8 p.m.; $32 for adults, $25 for those under 18); or Naumkeag, which illuminates its gardens with a popular, kid-friendly Pumpkin Show for the month of October (Wednesdays through Sundays, from 5 p.m. to 9 p.m.; $25 for adults and free for children under 15 on Wednesday and Thursday “Value Nights”).
If the weather turns, the Berkshires’ museum scene exceeds anything in the Hamptons or Hudson Valley.
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scene → check → Hamptons
The Clark Art Institute in Williamstown pairs Impressionist masterworks with 140 acres of trails and landscape art.
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Institute → pair → trails
The Norman Rockwell Museum in Stockbridge houses the largest collection of the all-American artist’s work anywhere.
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Museum → house → work
And Mass MoCA in North Adams fills a converted 19th-century factory complex with room-sized installations that compete with anything you’d see at MoMA or Manhattan’s spendy galleries.
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you → fill → MoMA
But this time of year, the Berkshires’ most important attraction remains its landscape.
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attraction → remain → year
To get up close and personal with that iconic New England fall foliage, consider apple picking with mountain views at Hilltop Orchards in Richmond, or strolling through the Berkshire Botanical Garden (general admission is $22, but it’s free on Tuesdays).
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it → get → Tuesdays
And, of course, the best walks remain free.
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walks → remain → course
There’s a lifetime’s worth of foliage hikes and outdoor routes — a perfect solution for those who would rather spend nothing beyond the gas it takes to drive there.
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it → ’ → gas
The Aporia
