The Berkshires

Culture seekers will find no shortage of attractions in Western Massachussetts’ mountains.

During the Gilded Age, moneyed Bostonians and New Yorkers (think Carnegie, Westinghouse, Vanderbilt, et al.) would escape the frenzy and filth of the cities and head to their stately “cottages” (read: mansions) in the bucolic Massachusetts Berkshires for a welcome, civilized respite from the pace and demands of urban life. Artists and writers, too—including Nathaniel Hawthorne, Herman Melville, Henry David Thoreau, Edith Wharton, and Norman Rockwell—have sought the tranquility and inspiration found amid the iconic tall pines, rolling hills, and verdant pastures of what became known as the “Inland Newport.” Today, urban and artistic influences, past and present, give the Berkshires an arresting combination of rustic, scenic beauty, cultural sophistication, and quintessential New England charm.

Most of the Berkshires’ towns and villages are dotted around Route 7, which serves as the commercial spine of the region. At 54 miles, Route 7 runs the entire length of the Berkshires from Sheffield, the southernmost town, to Williamstown, the northernmost.

If a walk down the street of a Berkshires town feels like you’re stepping into a Norman Rockwell painting (you’ll see mom-and-pop shops, antique stores, art galleries, and chef-owned eateries), it’s for good reason—Rockwell lived most of his life here (in Stockbridge). The Norman Rockwell Museum, located on the outskirts of Stockbridge, exhibits the single largest collection of the artist’s work. 

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The region’s other notable museums include the Clark Art Institute in Williamstown and The Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams. The Clark, which completed a major renovation in 2014, features an eclectic exhibit of 19th- and 20th-century American and European paintings, Impressionist art, and a stunning silver collection. 

Other attractions worth adding to your itinerary include The Mount, author Edith Wharton’s home and gardens, in Lenox; Arrowhead, Herman Melville’s home-turned-museum (where he penned Moby-Dick), in Pittsfield; and Ventfort Hall, one of the original surviving cottages-turned-museum of the Gilded Age. Serious antiquers should head to Sheffield, where many of the region’s best antique and vintage stores are clustered, while nature lovers should avail themselves of the walking and hiking opportunities in the region’s countless state parks and forests, especially Beartown in Monterey, and October Mountain in Lee, the largest forest in the state.


• Distance from White Plains: 2 hours to Great Barrington
• Location: The Berkshires are located in Berkshire County, Massachusetts, and are bordered by Vermont to the north, New York to the west, and Connecticut to the south.
• Population: 129,585 (as of 2013)
• Highest Peak: Mount Greylock (3,491 ft) in Adams; summit is accessible by car. (Great photo op!)
• Best Known for: Norman Rockwell; Tanglewood (summer home of the Boston Symphony); BerkShares, an alternative local currency(!) (


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The foliage typically peaks in the northern Berkshires (above Pittsfield) during the first week of October and in the southern Berkshires during the second week. While Route 7 is the main corridor in the Berkshires, Route 8, which runs mostly parallel to it, offers a less developed and more scenic experience. Another less-traveled choice is Route 183, from Lenox to Great Barrington. For scenic foliage walks, the flat, 1.5-mile loop trail encircling Benedict Pond in Beartown State Forest in Monterey provides great photo ops. More ambitious walkers can hike one of two trails (easy or steep) to the 1,642-foot-high summit of Monument Mountain in Great Barrington, for a breathtaking panorama of Berkshires foliage at its best. 

The lobby at The Gateways Inn recalls its private mansion past


The Berkshire Botanical Gardens in Stockbridge hosts the Berkshires’ annual Harvest Festival on its grounds. With more than 10,000 attendees annually, it is one of the country’s largest and longest-running harvest festivals, combining live music; crafts, food, and a farmers’ market with more than 100 vendors; book, plant, and tag sales; and children’s activities. This year’s festival will be held October 10 and 11. (


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Hotel on North 

Opened June 1 of this year, Hotel on North comprises a pair of 1880s buildings in downtown Pittsfield that are on the National Register of Historic Places. Mixing 19th-century and industrial chic motifs, this 45-room boutique hotel offers exceptional attention from its staff and the best location in the Berkshires, with all other Berkshire County towns and attractions within a 30 to 40 minute radius. Furnished with locally crafted furniture and décor, the spacious hotel features all of the amenities you’d expect from a more urban hotel, such as 24/7 valet parking, a fitness center, gift shop, art gallery, bar, lounge, restaurant (Eat + Drink on North), and late-night room service. Room amenities include an oversized walk-in shower with rain showerhead, minibar, in-room coffee maker, refrigerator, separate sitting area with second flat-screen TV, and Bluetooth-enabled sound system. Some rooms include a fireplace, kitchenette, and claw-foot soaking tub. The hotel’s inviting common areas (especially its three sky-lit atrium lounges) are perfect for relaxing or socializing. 

297 North St, Pittsfield, Massachusetts
(413) 358-4741
Rates begin at $259/night in September and $179/night beginning October 13

One of The Barrington’s eight suites, all of which are 500+ square feet

The Barrington

Opened in 2014, The Barrington offers the personal touch of a B&B with the convenience of hotel accommodations. The boutique property is located on the third floor of a building right on Main Street, making it the only accommodations residing in the walkable part of downtown Great Barrington—putting the town’s myriad shops, bars, restaurants, and theaters literally steps away from your oh-so-comfy queen-size poster bed. The property’s eight salon-suites also feature flat-screen TVs, Keurig coffee makers, refrigerators, separate sitting areas, and spacious bathrooms with walk-in showers. In the morning, you have a choice of made-to-order breakfast delivered to your room or credit toward breakfast at a restaurant in town.

281 Main St, Great Barrington, Massachusetts 
(413) 528-6159;
Rates begin at $235/night

The Gateways Inn 

Located in the heart of Lenox, this 11-room bed and breakfast perfectly blends old-world charm and elegance with modern-day luxury. The former Procter mansion features sleigh beds (complete with a teddy bear), fireplaces, plush robes, coffee makers, and mini-refrigerators. Innkeepers Michele and Eiran Gazit will even stock your refrigerator with breakfast should you need to leave in the morning before breakfast is served. The restaurant at The Gateways Inn offers delicious Mediterranean seasonal cuisine, and The Lounge features live music, and serves late-night fare. The bar has an impressive selection of whiskies (more than 200, of which half are Scotch). Within walking distance of Tanglewood, The Gateways Inn is also a good choice for summer, but make sure you book early.

51 Walker St, Lenox, Massachusetts
(413) 637-2532;
Rates begin at $170 per night, with a two-night minimum from June to October


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