15 Best Things to Do in the Berkshires

The Berkshires, a rural mountain region in western Massachusetts, draws countless visitors every year thanks to its fascinating history, ample outdoor activities, burgeoning food scene, and incredible shopping. The area's charming towns, including Lenox, Stockbridge, and Great Barrington, offer a surprising number of activities for every type of traveler.

Culture seekers will appreciate the Norman Rockwell Museum and the Tanglewood music venue, while nature lovers will find no shortage of trails with spectacular views. Whether you're in the mood for history or craft beer, here are some of the best things to do in the Berkshires, no matter the season.

Catch a concert at Tanglewood.

This open-air music venue in Stockbridge serves as the summer home of the Boston Symphony Orchestra. While the lush grounds and expansive lawns are open all year round (free of charge), you'll want to plan your trip during the summertime, when you can listen to music under the stars. (Bringing along a delicious dinner and cozy blanket is highly recommended.) Event programming is always rotating, but previous acts include performances from Ringo Starr & His All-Starr Band, James Taylor, the Juilliard String Quartet, and The Black Crowes, to name a few.

Go shopping in Lenox.

Lenox is famous for its charming downtown area dotted with eclectic boutiques and one-of-a-kind shops. Pick up some unique home goods at Annie Selke Shop, Design Menagerie, or MacKimmie Co.; add to your wardrobe with staples from Catwalk Boutique, or Purple Plume; or grab some vacation reading material (and enjoy a glass of vino) at The Bookstore & Get Lit Wine Bar. Meanwhile, gourmands can peruse the aisles of Oliva Gourmet Olive Oils & Vinegars and Dare Bottleshop & Provisions.

Hike Mount Greylock.

At nearly 3,500 feet tall, Mount Greylock is the highest point in the state of Massachusetts. The entire Mount Greylock State Reservation spans around 12,000 acres and boasts several hiking trails, including a stretch of the famous Appalachian Trail. At the summit, visitors can stop at the Veterans War Memorial Tower, a 93-foot granite lighthouse with 89 steps leading to an observation deck. From there, enjoy panoramic views stretching across five states (Massachusetts, New York, Connecticut, Vermont, and New Hampshire).

Eat your way through Great Barrington.

The streets of Great Barrington are lined with tasty restaurants that'll satisfy a range of cravings. Keep it casual at Baba Louie's, famous for its selection of sourdough pizzas. For authentic Mexican staples like mole and margaritas, head straight to Xicohtencatl, which occupies a striking yellow house with a sprawling porch. Prairie Whale is a dinner-only haunt known for its rustic-chic aesthetic, lively ambience, elevated American entrees featuring locally sourced ingredients, and creative cocktails. For a true treat, make a reservation at Number Ten, which serves up all sorts of steaks, poultry, and seafood, plus mouthwatering sides like creamed spinach, mac and cheese, and mashed potatoes.

Check out the Norman Rockwell Museum.

Founded in 1969, the Norman Rockwell Museum in Stockbridge boasts an expansive selection of the artist's work — almost 1,000 original paintings and drawings, to be exact. (Rockwell lived in the town from 1953 until 1978, when he died.) The 36-acre campus is home to 10 galleries, the artist's beloved Stockbridge studio (which was moved here in 1986), and an impressive collection of 100,000-plus items that range from personal calendars to fan mail.

Embark on your own dessert trail.

Grab a sweet treat (or three) at one of the many dessert spots in and around the Berkshires. In Pittsfield, indulge in some summertime soft serve at Dairy Cone. Then, make your way to Lenox to check out the seasonal Sweet Dreams cafe, which sells crowd-pleasing pastries like cinnamon buns and chocolate chip cookies, or the beloved Chocolate Springs Cafe for specially crafted confections like truffles, chocolate-covered pretzels, and marshmallows. Candy lovers of all ages will also appreciate the nostalgia-inducing Robin's Candy, a Great Barrington shop stocked with a curated collection of sweets to suit every palate. Another nearby favorite is the Parisian-inspired Pixie Boulangerie.

Travel back in time at Hancock Shaker Village.

Learn more about Shaker history at Hancock Shaker Village, which dates back to the late 1700s. Today, the site has been transformed into a living history museum with a working farm, a one-mile walking trail, and thousands of fascinating artifacts (think: furniture, tools, textiles, and more). It's also worth noting that Hancock Shaker Village is open seasonally (typically from mid-April through October), so plan your visit accordingly.

Get out on the lakes.

The Berkshires is home to dozens of pristine lakes for swimming, paddling, boating, and fishing. The 511-acre Pontoosuc Lake is among the region's most scenic, and its bright blue waters make it a popular spot for boating. Pack a picnic lunch, some towels, and a chair to lounge on the grassy lawns along the shore. With the Berkshires being one of the best fall vacation destinations, it's no surprise the lake is also a must-visit for foliage views when the surrounding trees turn fiery red, orange, and yellow. Meanwhile, Lake Onota is slightly larger at 617 acres. Here, you can relax along the sandy beach area before heading into the water to swim, kayak, or canoe.

Wander through Mass MoCA.

The Massachusetts Museum of Contemporary Art (Mass MoCA) in North Adams offers a whopping 250,000 square feet of gallery space, so be sure to carve out enough time to explore it all. Expect to be dazzled by an array of extravagant masterpieces, including eye-catching ceramics, interactive exhibitions complete with lights and sounds, larger-than-life wall drawings, and striking sculptures.

Get a taste of everything at the Berkshire Museum.

Get a little more culture during your visit with a stop at the Berkshire Museum in Pittsfield. Here, guests can explore the museum's vast and varied collection of more than 40,000 objects in its exhibits and at community events. According to the museum's website, its founder, Zenas Crane, was inspired by the American Museum of Natural History, the Smithsonian, and the Metropolitan Museum of Art, and decided to combine all their best attributes into one space. Thus, the Berkshire Museum makes it possible to see fine art, natural science, and history exhibits under one roof. 

Indulge your bibliophile dreams at Edith Wharton's The Mount.

One of the best things to do in the Berkshires is visit The Mount, the former home of author Edith Wharton, who wrote books like "The Age of Innocence" and "The House of Mirth." The property is now a National Historic Landmark and cultural center dedicated to preserving the space and her legacy. Guests can come to tour the gardens, the home's interiors, and a rotating list of exhibits showcasing both literature and life during the early 20th century. Visitors can even come for a quick ghost tour of the property — if they dare.

Pluck the perfect apple at Hilltop Orchards.

Participate in one of the area's favorite fall pastimes — apple picking — with a visit to Hilltop Orchards. The farm, located just on the edge of the Massachusetts and New York border, has been a Berkshire institution for more than a century. Guests can pick (and eat) 27 different apple varieties come fall and indulge in a sweet cider donut, too. Not visiting the area during the autumn? No problem — the orchard is open year-round and offers cidery tours and tastings, as well as access to its trail system, spread across the 200-acre grounds, which are ideal for hiking in the spring, summer, and fall, and snowshoeing all winter long.

Seek out more art at The Clark Art Institute. 

Another stellar cultural institution in the Berkshires, The Clark Art Institute has been open to the public since 1955 and has a dual purpose. In addition to preserving the classics as a museum, it's also a research center dedicated to higher education and expanding the public understanding of art. Come explore its permanent and rotating exhibitions, which have spotlighted international artists such as Edvard Munch and Pierre-Auguste Renoir. If you have some extra time, don't forget to marvel at its spectacular 140-acre campus grounds, too. 

Take a ride at the Berkshire Scenic Railway Museum.

Weave your way through some of the area's most beautiful landscapes with a ride on a historic railway. The Berkshire Scenic Railway Museum, founded in Lenox in 1984, aims to preserve the railway and its history by maintaining historical data and equipment. It also offers visitors the chance to hop aboard for fun seasonal rides. Excursions include a fall foliage trip, a winter Santa train, and more. Check out the railway's website to see what's available when you visit. 

Toast to a successful trip.

Cap off a fun-filled trip at one of the nearby breweries, wineries, or cideries. Oenophiles will especially appreciate Balderdash Cellars, where you can lounge on a lawn overlooking a lake. For craft brews, make your way to Wandering Star Craft Brewery, Berkshire Brewing Company, or Big Elm Brewing. Alternatively, if you prefer cider, look no further than the Berkshire Cider Project.