The Berkshires

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

At A Glance: Distance from the Main Line: 4 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(!)


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 Berkshires for a welcome, civilized respite from the pace and demands of urban life. 

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. 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. 

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


Hotel on North 

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

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. 

The Barrington

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

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 a made-to-order breakfast delivered to your room or credit toward breakfast at a restaurant in town.

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The lobby at The Gateways Inn recalls its private mansion past.

The Gateways Inn 

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

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.


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, Route 8, which runs mostly parallel to it, is less developed and more scenic. 


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. This year’s event will be held Oct. 10 and 11.

Our Best of the Main Line Elimination Ballot is open through February 22!