Tire + Wheel Insurance Sidebar Advertisement

The Top 10 Things to Do in the Berkshires, Mass.

cranwell mansion in the berkshires

What’s not to love about a place where you can listen to a world-famous orchestra as you picnic, go hiking and antiquing in the same day, and visit cool museums? That place is the Berkshires, a hilly corner of western Massachusetts where the focus is on living well via active pursuits, cultural immersion and culinary indulgence. And it doesn’t hurt that the Berkshires features some of the Northeast’s most beautiful landscapes. Here is what to do in the Berkshires when you visit.

102 National Park Attractions

See the most beautiful sights in America with help from this Your AAA guide to national parks.

Download Now!

Top 10 things to do in the Berkshires, Mass.


When summer arrives, the Boston Symphony Orchestra decamps to Tanglewood, a 529-acre music complex in the town of Lenox, where it performs in the Koussevitzky Music Shed from late June to early September. The 5,100-seat performance complex has been home to the orchestra since 1937.

Rockwell’s Studio (Photo: Art Evans. ©Norman Rockwell Museum)


Nostalgic Americana awaits at the Norman Rockwell Museum in Stockbridge, where 998 of the artist’s paintings and drawings reside. It is also home to a collection of over 100,000 other items like photographs, fan mail and more. Pair a visit with lunch at the atmospheric Red Lion Inn, established in 1773.


There are plenty of places to hike in the Berkshires – even a 15-mile segment of the Appalachian Trail. Hardy trekkers can tackle its most rugged section and climb 3,491-foot Mount Greylock  for a panoramic view. And thrill-seekers can get their wet adrenaline fix at Crab Apple Whitewater, a family owned and operated whitewater rafting outpost that provides nothing but memorable experiences.


Head to Lenox for dinner, where options include upscale chow at Table Six, a fine-dining restaurant with unbeatable décor and an amazing outdoor view. Or try local cuisine at the cozy and casual Nudel, where farm-fresh feasts are a fact of life. Other spots include Alta Restaurant & Wine Bar, where you can taste Mediterranean delights (and 24 wines by the glass).


This region is known as Antiques Alley, and the browsing opportunities are non-stop along Route 7, where you will find specialized shops as well as the multi-dealer Great Barrington Antiques Center. Peruse the thousands of collectables, art and antiques in the 5,000-square-foot shop, which is open seven days a week from 10 a.m. to 5 p.m. daily (they close on Wednesdays during the winter). Their inventory of oriental carpets, antique furniture and more changes daily, so you never know what you will find during your next stop.


Contemporary art lovers can check the schedule at MASS MoCA in North Adams, where both temporary and long-term exhibitions ­– notably 105 wall drawings by Sol LeWitt – are on display. The converted factory building is one of the largest centers for art and performance art in the United States. Other exhibitions on display include a presentation of work by German painter and sculptor Anselm Kiefer and a project that shows the growth of six live – and inverted – trees.


Whether you prefer wine, beer or distilled spirits, sampling local artisanal brews makes for a fun afternoon. Options include Balderdash CellarsBig Elm Brewing and Berkshire Mountain Distillers. Try the Truth Serum Albariño at Balderdash for a light and crisp taste with a hint of lime. The 413 Belgian ale brewed with chamomile and orange zest at Big Elm is also a treat, as is the Greylock Gin at Berkshire Distillers.

Beet and blue cheese salad at Allium (Photo: Angela Cardinali)


Known for its wood-fired sourdough-crust pizzas, Baba Louie’s in Great Barrington is a hotspot. The Isabella Pizzarella is a delicious pizza option with roasted sweet potatoes, roasted parsnips, shaved fennel and balsamic vinegar. So is the Pomodoro Bianco, which is topped with fresh mozzarella, roasted portabellas, goat cheese and pesto.


At the Sterling and Francine Clark Art Institute in Williamstown, you can browse amid work from impressionist masters like Claude Monet, Camille Pissarro and Pierre-Auguste Renoir. Established in 1955, the museum and research institution is home to Renoir’s “Self-portrait,” Monet’s “The Cliffs at Etretat and Pissarro’s “The Road: Rain Effect.” Plus, there are many other European and American paintings, sculptures, drawings and photographs from the 14th century to the 20th century.

Sterling and Francine Clark Art Institute (Credit: Jeff Goldberg / Esto)


Golfing is a top activity here from May through October. There are more than a dozen courses with options that include Cranwell Golf Club in Lenox and Wahconah Country Club in Dalton. Bas Ridge Golf Course in Hinsdale and the Blandford Golf & Tennis Club in Blandford are also open to the public. But call ahead for tee times because the word is out on the Berkshires. The area offers so much more than just an amazing place for hiking and camping – although it’s perfect for that too.

Looking for a variety of great lodging options in the area? Find and book great hotels in the BerkshiresCall 1-800-873-8283 to speak to a AAA travel counselor today or click here.


Sign up and receive updates for all of the latest articles on automotive, travel, money, lifestyle and so much more!

3 Thoughts on “The Top 10 Things to Do in the Berkshires, Mass.

Leave A Comment

Comments are subject to moderation and may or may not be published at the editor’s discretion. Only comments that are relevant to the article and add value to the Your AAA community will be considered. Comments may be edited for clarity and length.