You’ll Love the Art, History and Beauty of Western Mass

Our suggestions for the best ways to spend your time time in Berkshire County

Berkshire County is located in the Western part of Massachusetts. It may be connected to Boston by the Mass Pike, but you will feel as if you are in a different state if you visit the Berkshires. The county has become a bit of a cultural center. It is the perfect place to spend a long weekend, especially during the summer. Here are some of the many places that you will want to visit in Berkshire County.

Red Lion Inn, Stockbridge / facebook

Red Lion Inn

30 Main Street, Stockbridge, MA, 01262

If you’re looking to have a memorable long weekend in the Berkshires, you’ll need someplace special to stay. The Red Lion Inn in Stockbridge is one of the most iconic places to rest that you will find in the state. The main building dates back to 1773, when it used to be a tavern. The Red Lion Inn is listed on the Historic Hotels of America, as well as the National Trust for Historic Preservation. Part of the charm of the Red Lion Inn is that the rooms are not all the same. In this day and age of cookie-cutter hotel rooms, that is a nice change of pace! If you don’t stay at the Red Lion Inn you can still drop by and dine in one of several different areas. It is a meal that you won’t soon forget.

Shakespeare & Company, Lenox / Facebook

Shakespeare & Company

70 Kemble Street, Lenox, MA, 01240

Being a cultural center, there is a fair amount of theater in Berkshire County. Shakespeare & Company goes a step above the rest because they are truly part of the community. The company is active in several local schools, giving students a new appreciation of the performing arts. There are also actor training programs for adults. There’s more to Shakespeare & Company than education. There are performances throughout the year, but the season comes alive in the summer. There will usually be at least two different Shakespearean classics rotating during the summer, and works by other playwrights could also be featured. You don’t have to be a fan of Shakespeare to love Shakespeare & Company.

Hancock Shaker Village, Pittsfield / Facebook

Hancock Shaker Village

1843 W Housatonic Street, Pittsfield, MA, 01201

The Shakers were a religious sect with roots that date back to 1747 in Manchester, England. Hancock Shaker Village was one of nineteen major villages where the followers settled in the New World. The Shakers were famous for the simple furniture that they designed and sold. They lived communally, and practiced abstinence. Hancock Shaker Village is a working recreation of sorts. It is staffed by Interpreters who will happily explain the Shaker way of life to you. Hancock Shaker Village is home to one of the most famous buildings in Berkshire County; the Round Stone Barn. In total there are 20 buildings spread over approximately ten acres. There is also a working farm. Hancock Shaker Village is open mid-April through October, although there are sometimes special events during the offseason.

Ventfort Hall Mansion and Gilded Age Museum, Lenox /

Ventfort Hall Mansion and Gilded Age Museum

104 Walker Street, Lenox, MA, 01240

While the Shakers lived a simple life, for a while the opposite was true of some residents of Lenox, Massachusetts. There are many mansions from the gilded age in the town. One that you can easily visit is Ventfort Hall. It’s located near the center of town, and the Ventfort Hall Association is actively working to restore the property to its former glory. Ventfort Hall was built in the late 1890s for George and Sarah Morgan, who was the sister of J.P. Morgan. Parts of the movie The Cider House Rules were filmed on the property. Guided tours are available daily, and there are special events held throughout the year. Ventfort Hall is a great place to visit when you have a couple of hours to explore during your long weekend. You can get a glimpse of what extreme luxury looks like.

Jacob’s Pillow /

Jacob’s Pillow Dance Festival

358 George Carter Road, Becket MA, 01223

For those who love the performing arts, Jacob’s Pillow is a must. It dates back to 1931. While Jacob’s Pillow has events and classes year-round, it is best known for the summer performances. The season runs from mid-June until late August. Different dance companies are featured, and various styles of dance are exhibited. There is more than one theater on the property, so you can catch two different types of performances in one day if you would like.

Norman Rockwell Museum / Facebook

Norman Rockwell Museum

9 Glendale Road, Stockbridge, MA, 01262

Norman Rockwell might have been known for his Saturday Evening Post covers in most of the country, but in Stockbridge, Massachusetts he was a well-loved resident for the last 25 years of his life. He was known for talking to people on the street about the possibility of painting them. He died in 1978, but his memory in the town lives on in the Normal Rockwell Museum. The museum is home to 574 of his original pieces, including some of his most famous paintings. The Norman Rockwell Archives contains over 100,000 items, including letters and rare photos. The Norman Rockwell Museum is open year round, with the exception of major holidays.

Tanglewood – Boston Symphony Orchestra /


297 West Street, Lenox, MA, 01240

Tanglewood is the main reason why Berkshire County is filled with tourists during the summer months. Dating back to 1937, it is the summer home of the Boston Symphony Orchestra. The season begins in the middle of June and runs through the beginning of September. You can purchase an assigned seat and watch from The Shed, or buy a Lawn ticket and listen to the music under the stars. There are more acts than just the Boston Symphony Orchestra at Tanglewood. James Taylor performs sold-out concerts every year as part of the Popular Artists series. Another well-loved yearly event is Film Night. The legendary John Williams will lead the Boston Pops in some of his iconic scores. Film Night will also feature guest artists and possibly another conductor. Tanglewood on Parade also features John Williams, as well as Boston Pops Conductor Keith Lockhart. You will want to arrive early and explore the grounds, they are spectacular. No matter who is performing or what the program is, Tanglewood offers a near-perfect time. It needs to be part of your long weekend.

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