Berkshires Road Trip To Discover Mansions, Music, Art, and Savory Delights

Discover History, Art, Music, and More on a Fun Berkshires Road Trip

Berkshires Road Trip

The Berkshires in western Massachusetts have been a favored getaway destination for generations.  Conveniently located about two hours from either Boston or New York City, cool summer breezes beckon vacationers to spend time roaming tree-lined country roads, rolling hills, and historic sites.  These hills are alive with grand gilded-age summer “cottages”, music, dance, art, and bucolic farms.

With so much to offer, our friends at have asked us to share some of the best sites to visit during a Berkshire getaway.  Whether you come for a weekend or a week, we recommend that you find a lovely hotel in centrally located Berkshire’s towns of Lenox or Stockbridge.  From here, all the best sites are just a short distance away.  Let’s take a look at the top places you won’t want to miss.

Norman Rockwell Museum

Norman Rockwell Museum

The Norman Rockwell Museum is perhaps the most engaging art museum you will ever visit.  Normal Rockwell has been beloved for generations for his ability to capture the magic and poignancy of everyday life.  His depictions of the humor and humanity in family life graced 357 covers of the Saturday Evening Post spanning 47 years.  Most people don’t realize that each cover image was first an original painting.  These wonderful paintings are all exhibited at the museum.  I was amazed by the colors and textures of the paintings that far outshine the printed magazine covers.  Plan to spend several hours at this museum savoring the paintings, dining in the cafe, and enjoying the grounds of its lovely hilltop setting.

Naumkeag House and Gardens

Flickr by:  Massachusets Office of Tourism

Just a short distance away you can tour this grand home that was the summer residence of NY attorney Joseph Choate.  This mansion retains its charm as a family home and not simply a showplace to impress the wealthy social scene that gravitated to the Berkshires during summer months.  The gardens at Naumkeag are something special.  There are 8 acres of terraced formal gardens closest to the house including a rose garden, afternoon garden, and Chinese garden.  Beyond are meadows, pastures, and woodlands.

The Mount

The Mount Lenox MA

Visit The Mount to get an insider’s peek into the life and times of the celebrated author, Edith Wharton, the first female author to win a Pulitzer Prize.  You may be familiar with her popular works that include Ethan Frome, The House of Mirth and The Buccaneers to name just a few.  The house was personally designed by Edith and reflects traditional design elements of England, France, and Italy.  Be sure to do opt for a docent-led tour to learn all the intricacies of the home and the often eccentric life of Edith and her husband.  The estate includes a magnificent home and stables, as well as lovely flower and sculpture gardens.  For an extra treat, sign up for the GHOST tour!

Local Farms

Perhaps you’d like to fill your own picnic basket!  Since picnicking is a popular pastime in the Berkshires, there’s no better way to fill your basket with treats than to visit a local farm.  There are two wonderful farms in the area that offer locally grown produce, plants, and dairy products.  Visit Windy Hill Farm for their array of apple varieties and blueberry fields.  High Lawn Farm is celebrated for its superb cheeses and dairy products.  Between the two stops, your basket is sure to be filled with culinary delights.

Ventforth Hall Mansion and Gilded Age Museum

Ventforth Hall
Flickr by: Massachusetts Office of Tourism

The stately Ventforth Hall Mansion is a prime example of the elaborate “summer cottages” built by wealthy summer residents during the late 1800’s.  This opulent 50 room Jacobean Revival mansion houses a museum dedicated to paying tribute to the “gilded age” when fortunes were spent constructing grand manor homes for seasonal use.  Enter the sweeping great hall and gaze up the magnificent winding staircase and beamed ceiling.  It remains as dramatic today as it was in the last century.  If you yearn to experience the lifestyle of the privileged set, then a visit here will tickle your fancy!


Tanglewood Boston Pops Orchestra
Wikimedia Commons by: Daderot

Tanglewood, the summer home of the Boston Symphony Orchestra has long defined summers in the Berkshires.  The Tanglewood complex now includes The Music Shed, Seiji Ozawa Hall, and three acclaimed music schools.  For generations, visitors have come to picnic on the lawns and hear the ‘hills come alive with the sound of music’.  One of the delightful perks of staying at a lovely hotel or inn in Lenox or Stockbridge is that they often offer to prepare a picnic basket for you to take along to Tanglewood for the day.  No matter what genre of music you prefer, there are most likely performances at Tanglewood to delight you.

Shakespeare & Company

You don’t have to travel to England to see a performance of the greatest works of William Shakespeare.  The Shakespeare & Company venue is often referred to as “The Bard in the Berkshires”.  Outdoor performances of Shakespeare and other noted plays are held at the new Spruce Theatre, an impressive 500-seat, terraced amphitheater surrounded by towering pine trees.

Final Thoughts

Since summer travel this year is bound to have some unexpected adjustments due to Covid-19 conditions, we would encourage you to make plans well in advance and to check with restaurants and attractions for new opening times and any restrictions.  Because of the pent-up demand for family holidays, vacation bookings for The Berkshires are in demand. It is very important to book your Berkshires hotels in popular towns like Lee, Lenox, Stockbridge, and Great Barrington, as quickly and early as possible.  With everyone looking forward to getting out in beautiful settings this summer, there’s no better place to plan a getaway than in the beautiful Berkshires.




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