Going: The Berkshires, MA

What are the Berkshires? Culturally, the term refers to the highland region west of the Connecticut River and lower Westfield River, but most know them as the range of mountains in western New England. Perfect for outdoor adventure, the Berkshires are one of the best summer vacation spots if you love to explore in style. With a plethora of art museums, high-end restaurants, romantic views, and incredible hiking trails, the Berkshires are truly an American treasure in every sense of the word.



One of the oldest mountain ranges in the world, dating back nearly 500 million years, the Berkshire Mountain range is comparable in size to the Himalayans, though without a peak like Everest. The rich and diverse forest provides habitat for a magnificent variety of animal wildlife and American culture. Bird watchers, leaf peepers, and mountain enthusiasts will feel right at home. History buffs and fans of American art will find multiple can’t miss sites of cultural significance.




No trip to the Berkshires would be complete without a trip to The Norman Rockwell Museum. The museum houses the world’s largest collection of the artist’s work, including 998 of his original paintings and drawings. His personal Stockbridge studio was moved to the museum site and is open to the public May through October, making the summer the peak season to explore the inner life of an American icon. The museum is also known for its beautifully manicured grounds, so pack lunch for an amazing afternoon picnic experience. One thing to keep in mind, however, is that the museum closes at 4pm Monday through Friday and at 5pm on weekends, so plan accordingly.



Literature buffs and historians should definitely consider a stop at Arrowhead Home, the home of American literary icon Herman Melville. It was at this farmstead where Melville found the solitude and beauty that inspired some of his best writing, and some of the greatest works of American literature, including Moby Dick. The home is known for its extraordinary view of nearby Mount Greylock. Even if you are unfamiliar with the works of Melville, the home offers an intimate look at the history of Berkshire County. Originally built in the 1740s, the Berkshire County Historical Society has taken great strides to preserve the farmstead’s authenticity and historical value. It is a truly unique window into 18th and 19th century American pastoral life.



If you’re looking for something a bit more adventurous, nearby Mount Greylock has some of the best hiking trails in the whole Berkshire region. The mountain stands at 3,491 feet tall and is the highest mountain in Massachusetts. It is also part of a trail network that runs through the Berkshires and Taconic Mountain ranges, meaning multiple paths and peaks to explore. There are several trails that lead to Greylock’s summit, and for the slightly less adventurous, there’s even a road for motorized vehicles and bicycles that takes visitors to the top.



Another peak worth viewing is Bear Mountain. The highest peak in Connecticut, Bear Mountain stands at 2,316 feet, but don’t be fooled by the shorter height; the trails at Bear Mountain are fairly strenuous and require one to be in good shape physically. It’s well worth the extra effort, however, as the mountain features some of the best views in the entire range. Hikers should look to start their adventure at the Undermountain Trail at Bear Mountain or starting at Lion’s Head, which boasts some of the shortest hikes with the best views.




Once all your hiking and sightseeing has worked up an appetite, you’ll want to explore some of the best restaurants New England has to offer. For farm-to-table dining with a high-class yet cozy atmosphere, it’s hard to beat Mezze Bistro and Bar located in Williamstown, MA. The restaurant is actually in an old homestead that is so tastefully curated, it could double as an art museum. Expect three course meals and fine dining with reasonable prices and an unbeatable atmosphere.

If you’re looking for something a bit sweeter, we highly recommend checking out The Lost Lamb in Stockbridge, MA. This Parisian style bakery has some of the finest croissants and cupcakes in New England and is well worth the trip. Pastry Chef Claire Raposo graduated top of her class from Le Cordon Bleu Paris at only 19 years old, so rest assured you’re getting an authentic Parisian pastry experience with a creative and youthful flare.




For lodging, there’s no better place to stay than the Wheatleigh. Built in 1893, this 16th century-style Florentine palazzo is set on 22 acres overlooking the Berkshire Mountains. The hotel has recently undergone a multimillion-dollar renovation and provides historical elegance with 21st century comfort. The hotel is only two and a half hours from New York and Boston with easy access by private plane. The Wheatleigh hotel and restaurant was recently awarded AA Five Diamond, meaning you don’t have to wander far to find some of the best dining in the area. When it comes to experiencing the Berkshires in all their old-world glory, there’s no better way to do it than at the Wheatleigh.