A short list of where to stay and dine in The Berkshires


Sumptuous accommodations at Cranwell

The scenic and historic Berkshires deserve at least a few days to fully appreciate the region’s beauty and rich culture. There is a wide range of accommodations in the region. At the top end are several top-drawer resorts located near Lenox, including Wheatleigh, know for its posh comfort and cuisine; Blantyre, a 220-acre former private estate now operated as a Relais et Chateaux-member luxury hotel; and Canyon Ranch, the continent’s premier wellness spa. Another grand resort and former estate is Cranwell, known for its spa and on-property golf course. But for those focused on taking in the area’s museums, historical attractions and performing arts festivals, there’s a good selection of country inns and chain hotels.


The dining room at The Red Lion Inn

One of the prime hoteliers in the area is Main Street Hospitality Group, with an entourage of properties anchored by the Red Lion Inn, a 120-year old fixture in Stockbridge with a colonial-era origin. The Red Lion consists of the large, four-storey main building and a 10 guest houses spread across a large campus in the center of this historic town where Norman Rockwell once painted in his studio on Main Street. The Red Lion’s antique-laden rooms and suites provide a cosy and convenient base for visits to the nearby Norman Rockwell Museum, as well as Tanglewood and Shakespeare & Company just minutes north in Lenox, and Jacob’s Pillow Dance Festival a short drive east. It is down the street from the Berkshire Theatre’s principal summer venues, the Fitzpatrick Main Stage and Unicorn Theatre.


A superior room the Williams Inn in Williamstown

The hotel group’s newest property opens in May in downtown Pittsfield, the Berkshires’ de facto capital. Hotel on North is a major renovation and repurposing of a pair of attached 1880s buildings on North Street, Pittsfield’s principal street. It will offer elegant accommodation in 45 rooms located on the upper floors, steps away from the theatres of Barrington Stage Company and Berkshire Theatre Group. Hotel on North will include the Eat and Drink Kitchen and Bar, with a menu featuring local and regional foods.

Main Street Group’s other properties are in the northern end of the Berkshires, near The Clark Institute and MASS MoCA art museums. In Williamstown, the Williams Inn sits on the village green on the edge of the Williams College campus. It is next door to the Williamstown Theatre Festival and a two-minute drive to The Clark. The prime accommodation for visitors to the venerable Ivy League school for more than a century, the Williams Inn has 124 rooms, a large dining room and adjacent bar, an indoor pool, hot tub, and sauna.


The Williams Inn on The Green is across the street from the Ivy League Williams College

Minutes east in North Adams, across the street from MASS MoCA, is The Porches Inn, a collection of former Victorian row houses renovated in 2001 into 47 guest rooms and suites. The key architectural features are, well, porches, of 145 feet and 95 feet connecting the clusters of buildings, painted in vibrant colours, which visually hold their own beside the vast museum complex next door.

North Adams is a busy service centre that celebrates its history beyond the MASS MoCA complex. One is on Furnace Street, a collection of former industrial buildings by the old railway station, and includes a great place for a burger or other great pub food, The Freight Yard Restaurant & Pub. Hamburgers are its specialty, with nine gourmet versions on the menu. Tucked away in the Furnace Street mall just off busy State Street (the main route south out of town), The Freight Yard is a popular spot for both Berkshires residents and MASS MoCa visitors.

For the more practically minded who seek comfort without historic ambience, most of the major hotel chains have hotels in the area. Among the best and newest is the Hampton Inn Berkshires, conveniently located between Lenox and Pittsfield, and a short drive from Herman Melville’s Arrowhead. Hampton Inns are known for their consistent quality across North America, and the Lenox property receives high scores by its guests on the Trip Advisor travel-rating website. The 79-room hotel has an indoor pool, workout room and a large cathedral-ceiling lounge and breakfast area. Well set back from bustling Route 7, it offers a quiet refuge after a busy day touring the Berkshires many attractions.


The elegant Cranwell has its own
championship 18-hole golf course

Travel Planner

The Berkshires Official web site: www.berkshires.org

Red Lion Inn, Stockbridge: www.redlioninn.com

Canyon Ranch, Lenox: www.canyonranch.com

Hampton Inn & Suites, Lenox: www.berkshirehampton.com

The Williams Inn, Williamstown: www.williamsinn.com

The Main Street Hospitality Group www.mainstreethospitalitygroup.com

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