Exploring the Berkshires was happening long before the Gilded Age. This area of New England in the United States has always attracted people from near and far.

Exploring the Berkshires

This very cultural and geographically stunning area of western Massachusetts and Connecticut, has been something that travellers have always put on their must do list. The Berkshires is especially popular in leaf peeping season, but attracts visitors year round.

Exploring the Berkshires

Where are the Berkshires?

The Berkshires are located in the western parts of Massachusetts and Connecticut. The Berkshires have always been the summer refuge of the rich and famous who built summer homes of grand proportions. It still attracts an affluent clientele, though not as exclusively as it once did. It is now a very popular summer retreat for New Yorkers escaping the city heat and heading to the mountains and to the cultural activities that have made the Berkshires so attractive. The Massachusetts section of the Appalachian Trail draw the trekkers and walkers, and other outdoor enthusiasts.


Exploring Lenox

Lenox town shows obvious wealth and always has. This was the summer playground to the Carnegie, Vanderbilt and Westinghouse families, who loved the peace and the serenity of this part of the Berkshires. Tanglewood as the summer home of the Boston Symphony Orchestra and the many theatre and art groups that exist here are a testament that it remains a cultural drawcard.

It is an easy town to wander around, and there are some very charming shops. There are some lovely restaurants, and Alta Restaurant &Wine Bar is our recommendation for great food and ambience, and a bit of star spotting too.

There are also some epic sunsets that we watched throughout the Berkshires.

Gateways Inns and Restaurant

The Mount is the country house of the famous American author Edith Wharton, who designed the house and its grounds and considered it her “first real home.” The estate, located in The Berkshires, is open to the public.

2 Plunkett St, Lenox, MA 01240


Try and see a show at Shakespeare & Company.

You are in the US version of Stratford-upon-Avon


70 Kemble St, Lenox, MA 01240

James Taylor lives nearby in Lenox. He is a renowned singer song writer who performed two impressive songs, buy cialis bali “Fire and Rain” and had his first No. 1 hit the following year with “You’ve Got a Friend”. He is also a treasured performer at Tanglewood.

It would be just wrong not to try some of the famous chocolates at the Chocolate Springs Cafe. Wrong, wrong, wrong.

55 Pittsfield Rd, Lenox, MA 01240


Exploring Stockbridge

The Norman Rockwell Museum, is “the world’s largest collection of original Norman Rockwell #travelCLICK TO TWEETart, including beloved paintings from The Saturday Evening Post and the Four Freedoms, and the best in the field of American illustration.

9 Route 183, Stockbridge, MA 01262



Stockbridge looks quite an alternate town judging by the people, and it has a nice little walking tour around the village, where you can see the Red Lion Hotel and explore the Mews Mall and some pleasant parks.


Exploring West Stockbridge

West Stockbridge is set on the Williams River, and both are worth walking around. Stop at No. Six Depot for a coffee and a bite to eat. It also has a great little art gallery attached.

6 Depot Street (the old train station), West Stockbridge, MA 01230

West Stockbridge


Exploring Pittsfield

This is an eclectic town and quite a multicultural town, known as the “Brooklyn of the Berkshires,” It was where Herman Melville wrote Moby Dick. This is a novel about a whale at sea, yet it was written here at Arrowhead in the Berkshires.

780 Holmes Road, Pittsfield, MA


The Berkshire Museum in Pittsfield features works by American artists, an Egyptian mummy, and antiquities from Classical Greece and Rome.

39 South St, Pittsfield, MA 01201


We wanted to visit the Hancock Shaker Village, but it is low season people.

1843 West Housatonic St. Pittsfield MA, 01201

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Staying in the Berkshires

You will be split for choice with a diverse range of accommodation options. Inns and B&B’s in the Berkshires are a really lovely way to enhance you experience. The Gateways Inns and Restaurant, Lenox MA is a part of the Distinctive Inns of New England.

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