Top of Mt. Greylock

Top of Mt. Greylock, photo by Monika Sosnowski.

The Berkshires is a relatively short drive from NYC and its suburbs, as well as Boston, New Haven, and Hartford – but it’s a world away in its feel.

Life operates at a slower pace here. The Berkshire Visitor’s Bureau has said of the Berkshires, it is a place where “nature sets the scene, but culture steals the show.” A truer statement has never been written.

Environmentally, the Berkshires is rural with rolling hills, which include Mount Greylock — Massachusetts’ tallest mountain and Herman Melville’s inspiration for Moby Dick. The Appalachian Trail cuts through the Berkshires, going through October Mountain in Lee and Lenox and hitting Mount Greylock where you can view five states (MA, CT, NY, VT and NH).

Outdoor Sports

If you’re an outdoor sports enthusiast, the Berkshires has it all!

Hiking and Animal Watching

We have fabulous hiking trails (Bash Bish Falls, Ashley Falls, Bartholomew’s Cobble, Monument Mountain, Lenox Mountain, October Mountain, and many more).

We have two fantastic Audubon Sanctuaries for hiking as well as bird and animal watching.


Do you prefer biking? Try out the Ashiwilticock Trail, a paved former rail trail turned hiking, biking and skating trail, which runs from the Berkshire Mall in Lanesborough north to Adams. It is approximately 22 miles round trip along water and rolling hills.


In the winter, the Berkshires offers plenty of opportunities for both Nordic and Cross Country skiing as well as snowshoeing. In the south are Catamount and Butternut, in central county there’s Bousquet, and in north county you’ll find Jiminy Peak. Cranwell Resort offers groomed trails for XC skiing in Lenox, and Canterbury Farm in Becket offers trails for both XC skiing as well as snowshoeing (rentals available too, with a discount when you show your Rookwood Inn key).

Water Sports

Laurel Lake, photo by Kara Thornton

Laurel Lake, photo by Kara Thornton

In the summer, if you’re into water sports, you can swim or boat in Laurel Lake. They have a boat ramp for your small pleasure craft. If canoeing or kayaking is your thing, the Arcadian Shop of Lenox rents, if you don’t have your own. They will even provide lessons.

Bring your boat to the Stockbridge Bowl and enjoy a day or evening on the lake. During Tanglewood season, a small watercraft is a perfect location from which to enjoy the wonderful music coming from the BSO. You can also enjoy Pontoosac and Onota Lakes in Pittsfield.

If a swimming pool is more your style, Berkshire West Athletic Club has a pool which is covered in the winter and open in the summer. Day passes are available for both the pool and the exercise equipment/classes. Lenox Fitness is another gym which offers day passes (show your Rookwood key for a discount here too!).

Cultural Attractions

In addition to its natural beauty, the Berkshires are famous for their cultural offerings.

We have a wealth of museums, theaters, dance and music which are native to our area. My book, Devouring the Berkshires – One Cultural Bite at a Time, is an arm chair traveler’s guide to the cultural institutions as well as a cookbook.

Museums Everywhere!

In Williamstown…

The most famous museum is probably the Sterling and Francine Clark Art Institute in Williamstown. They are best known for their amazing collection of impressionist paintings; although their permanent and visiting exhibits are always world renown.

The Williams College Museum of Art, nearby, also has a lovely collection of work. In the neighboring town of North Adams is the Massachusetts Museum of Contemporary Art (MassMoCA) which houses some fascinating examples of modern and even futuristic art. Our guests always leave with an impression!

In Pittsfield…

In Pittsfield, there’s the Berkshire Museum which houses an impressive collection of Hudson River School paintings, a small movie theater, which shows foreign and arts films, a small aquarium, and many wonderful visiting exhibits.

Hancock Shaker Village

Hancock Shaker Village

In Hancock…

Hancock Shaker Village, in Hancock, is a living history museum of the Shakers. Here you can experience what life was like for these people in the 1930’s. Explore their farm, learn about heirloom breed animals and heirloom seeds. Attend one of their special days of quilts or antiques. Hear and see performances of their songs and dances, which were done as they worked for everything they did was done for God.

In Stockbridge…

The Norman Rockwell Museum, in Stockbridge, houses collections of his art as well as visiting exhibits. You can walk along the Housatonic River and visit Rockwell’s studio too.

Chesterwood, the home and studio of Daniel Chester French, the sculptor of the Lincoln Memorial and the Minuteman. Visit his home, walk the property’s many acres, enjoy the outdoor sculpture show in the summer, and learn about how he created his majestic masterpieces.

Berkshires Botanical Garden, photo by Kara Thornton

Berkshires Botanical Garden, photo by Kara Thornton

Up the street is the Berkshire Botanical Garden with acres of plants and flowers! Special events like art shows, antiques fairs and their fall harvest festival are not to be missed. The winter festival includes botany competitions as well as a sale of wreaths and greens for your home and for the birds! Naumkeag is a beautiful house museum and gardens. This was the estate of Choate and the gardens were once featured in a PBS program with Audrey Hepburn on the wonders of the world.

In Lenox…

Back in Lenox, there are a few more house-type museums: The Mount (Edith Wharton’s home), the Freylinghausen-Morris Home and Studio, and Ventfort Hall.

The Mount, located in Lenox is the home and gardens of Edith Wharton, an American treasure. She was a very prolific writer, fantastic gardener, and devotee of style. Her home is still in the process of being restored but is well worth the tour. The gardens are fabulous!

The Freylinghausen Morris Home and Studio also located in Lenox is a hidden gem. The museum is open from Memorial Day through Columbus Day and is an example of Bauhaus architecture and showcases these two artists’ works as well as their contemporaries such as Picasso. Tours of their home and studio are available.

Also in Lenox is Ventfort Hall built as a wedding present for Sarah Morgan, the sister of J.P. Morgan. Today you can tour the home, attend a lecture or tea, or perhaps participate in a dance. Venfort Hall’s exterior was used for outdoor shots of the orphanage in Cider House Rules.

The Arrowhead is a beautiful 1780s farmhouse which was Herman Melville’s home during his most productive years, 1850–1863. Here, Melville wrote his most famous novel, Moby-Dick (inspired by Mount Greylock).

In Lee…

Don’t leave the Berkshires without experiencing Animagic – Museum of Animation. Take a tour of the museum and see original models used in movies such as The Matrix, X-Men and Chicken Run. See a real Academy Award won by one of the co-owners. After the tour, create your own model, make an animation movie, record your movie on the computer, add sound, music and title and have your movie uploaded to YouTube! Open daily, by appointment.

World-class Culture

No visit to the Berkshires would be complete without some culture. We have theater, music, and dance.


Berkshire Theatre Group offers classical performances, musicals, and new plays along with performances of comedians and music in three different venues.

Barrington Stage has a full season of drama, comedy, and musicals on their stages in Pittsfield.

In Lenox, Shakespeare & Company has a year-round schedule which includes works by William Shakespeare, as well as other playwrights.


Tanglewood, Lenox, MA

Tanglewood in Lenox, MA, photo courtesy of Berkshire Visitors Bureau

Probably the best known cultural venue in the Berkshires is Tanglewood, the summer home of the Boston Symphony.

You may purchase Shed or Ozawa Hall seats or do like the locals and bring your lawn chairs and blankets, even a table and picnic. You can even do it up high style like some and bring your candelabra, flowers, and wine.


If it is dance that you crave, then make sure you go to Jacob’s Pillow. Here you will be surrounded by nature while you watch traditional, modern dance or ballet or an avant garde performance. Inside Out shows are held before performances on Tuesdays outside at no charge.


Whatever your preference, there’s something for everyone here in the Berkshires. Each season is special and unique. So, don’ t hesitate, make a reservation at The Rookwood Inn — we will be waiting for you!