The Berkshires, Massachusetts: Best Things to Do - Top Picks

The Berkshires in Western Massachusetts is a treasure trove of natural beauty and culture. It's a place where travelers from everywhere come to explore. But what makes it so special?

Here, you can enjoy top-notch music festivals and quaint towns. The Berkshires are perfect for outdoor lovers, culture seekers, and food enthusiasts. Whether you want to hike, visit museums, or stroll through charming streets, you'll find something to love.

Key Takeaways

• The Berkshires are a popular vacation destination in Western Massachusetts, known for their natural beauty, cultural attractions, and outdoor activities.
• The region is easily accessible from Boston, with a driving time of around 2.5 hours.
• Tanglewood, the summer home of the Boston Symphony Orchestra, hosts performances throughout the summer and fall.
• Visitors can explore historic sites like The Mount (Edith Wharton's former home) and the Hancock Shaker Village.
• The Berkshires are home to a thriving food and beverage scene, with local breweries, wineries, and cideries to discover.

Tanglewood: Summer Home of the Boston Symphony Orchestra

Tanglewood is in the beautiful Berkshires of Massachusetts. It's the summer home of the famous Boston Symphony Orchestra. For years, it has drawn music fans with its wide range of concerts under the stars.

Open-Air Concert Venue for Music Lovers

The Koussevitzky Music Shed and the lawns around it make Tanglewood special. People can sit on the grass with blankets and enjoy the music. It's a magical place for live music events.

The Boston Symphony Orchestra started playing at Tanglewood in 1936. Since then, it has welcomed famous artists like Yo-Yo Ma and James Taylor. These performances have made Tanglewood a place of unforgettable music moments.

Picnic Baskets and Lawn Seating

Visitors can bring their own food and blankets to Tanglewood. The lawn turns into a lively spot for families and friends. They can enjoy the summer evenings and the music of the Boston Symphony Orchestra.

Tanglewood is a top spot for music fans in the Berkshires. Its beautiful setting, rich history, and welcoming vibe make it a must-see.

Downtown Lenox: Charming Boutiques and Dining

The heart of the Berkshires, Lenox's downtown, is full of unique shops. You can find everything from home goods to special items at places like Annie Selke Shop, Design Menagerie, and MacKimmie Co.

Lenox is more than just shops. It's also known for its food scene. You can enjoy everything from casual meals to fancy farm-to-table dishes in downtown Lenox.

Walking through Lenox, you'll love the old buildings and New England feel. It's a place where shopping, eating, and culture come together. Downtown Lenox is a top spot for anyone visiting Massachusetts.

Looking for a hearty meal or something fancy? Downtown Lenox has it all. The food scene is lively, with everything from cozy cafes to fancy restaurants.

"Lenox is a true gem in the Berkshires, offering a perfect blend of shopping, dining, and cultural charm. I could spend hours exploring the unique boutiques and savoring the delicious local cuisine."

Mount Greylock: Hiking and Scenic Vistas

Mount Greylock is in the heart of the Berkshires, standing at 3,491 feet. It's the highest point in Massachusetts. It offers many hiking trails, including the famous Appalachian Trail. These trails go through the 12,000-acre Mount Greylock State Reservation.

Appalachian Trail and Summit Tower

Hikers love the Appalachian Trail on Mount Greylock. It takes about 1 hour and 30 minutes to reach the summit. The view from the top is amazing.

At the summit, you'll find the 93-foot Veterans War Memorial Tower. It offers views of five states: Massachusetts, New York, Connecticut, Vermont, and New Hampshire.

Panoramic Views Across Five States

The summit of Mount Greylock has incredible views. You can see the Berkshires' beauty and landmarks in other states. It's perfect for hikers and nature lovers.

Mount Greylock is a top spot in the Berkshires. It has great trails and views. It's perfect for anyone who loves the outdoors.

Great Barrington's Culinary Scene

Great Barrington is a food lover's dream, with many restaurants to choose from. You can enjoy sourdough pizzas at Baba Louie's or try authentic Mexican dishes at Xicohtencatl. The town's streets are filled with the flavors of the region's food culture.

For those who love American food made with local ingredients, Prairie Whale is a top choice. Chef Mark Firth's restaurant offers creative takes on classic dishes, like pig head rillettes and brick chicken. Nearby, Number Ten offers a wide range of steaks, poultry, and seafood.

Great Barrington also has unique dining spots. The family-run Asian market offers tasty ramen, sushi, and poke. The Bistro Box is famous for its fresh, local ingredient sandwiches.

Looking for a quick snack or a fancy meal? Great Barrington has it all. With a focus on local ingredients and a variety of dishes, it's a top spot for food lovers.

"Great Barrington's culinary scene is a symphony of flavors, celebrating the region's abundant local produce and the creativity of its talented chefs." - Fabia Raquel Atherton, co-owner of Brazzucas Marketplace

The Norman Rockwell Museum

In the heart of Stockbridge, Massachusetts, the Norman Rockwell Museum celebrates one of America's most loved artists. This 36-acre campus is home to nearly 1,000 original paintings and drawings by Rockwell. It gives visitors a special look into his artistic journey.

As you enter, you'll see 10 galleries filled with Rockwell's iconic works. Each gallery is a vivid picture of American life. You'll find the stories behind his famous illustrations, like the Four Freedoms series and Saturday Evening Post covers.

The Norman Rockwell Museum is more than art. It's a tribute to the artist's legacy. You can see Rockwell's Stockbridge studio and learn about illustration through interactive exhibits and programs.

If you love art, history, or storytelling, visiting the Norman Rockwell Museum is a must. It will captivate, inspire, and change you with the timeless art of this American icon.

Sweet Treats and Dessert Spots

The Berkshires is a paradise for sweet lovers. You'll find everything from quaint candy shops to artisanal bakeries. There's a wide range of desserts, sweets, and pastries to enjoy. Whether you want creamy ice cream or rich candy, the Berkshires has it all.

Candy Shops and Bakeries Galore

In Pittsfield, Dairy Cone is a favorite for soft-serve ice cream. Lenox's Sweet Dreams Cafe offers seasonal pastries and baked goods. Chocolate Springs Cafe in Lenox tempts with its specialty confections.

Great Barrington's Robin's Candy has a vast selection of candy. Pixie Boulangerie in Great Barrington offers French-inspired desserts and bakery treats.

"The Berkshires is a true haven for those with a sweet tooth. From soft-serve ice cream to decadent pastries and confections, there's something to satisfy every craving."

Looking for a classic candy bar or something new? The Berkshires is full of sweet spots. Treat your taste buds and explore the region's culinary wonders.

Hancock Shaker Village: Living History Museum

Hancock Shaker Village is in the heart of the Berkshires. It's a living history museum that takes you back to the Shaker world. This 750-acre site, from the late 1700s, shows the Shaker life through artifacts, a working farm, and hands-on experiences.

Walking through the village's 20 Shaker buildings, you see lots of Shaker artifacts. These include furniture, tools, and textiles made with great care. The buildings are well-preserved, making you feel like you've traveled back in time. You learn about the Shakers' simple, innovative, and community-focused way of life.

The village's working farm is a highlight. Here, you can see the Shakers' farming methods up close. You can help with the crops and watch the animals. It's a real way to connect with the Shakers' self-sufficient lifestyle.

The museum also has a one-mile walking trail. It shows off the beautiful landscape around the village. Walking here, you feel the Shakers' love for nature and their peaceful relationship with the environment.

Hancock Shaker Village is great for anyone interested in Shaker history or just wants to experience something unique. It's a place of rich heritage, educational programs, and stunning views. It's a place that can teach and inspire people of all ages.

The village is open from mid-April to October. This lets visitors see the Shakers' farming change with the seasons. Tickets cost $20 for adults, $8 for kids 13-17, and are free for kids 12 and under. It's a family-friendly spot that's easy on the wallet.

The Berkshires, Massachusetts: Best Things to Do - Top Picks

The Berkshires in Western Massachusetts is full of fun activities. You can explore world-class museums, enjoy outdoor adventures, and try delicious food. This New England spot has something special for everyone, whether you love music, art, history, or nature.

If you love music, don't miss Tanglewood. It's the summer home of the Boston Symphony Orchestra. Here, you can listen to music while having a picnic on the lawn.

Lenox's downtown is a treat with its shops, galleries, and great food. Nearby, Mount Greylock has amazing hiking trails and views of five states from its summit.

Art fans will enjoy the Norman Rockwell Museum in Stockbridge and the Massachusetts Museum of Contemporary Art (Mass MoCA) in North Adams. For history buffs, the Hancock Shaker Village offers a peek into Shaker life.

The Berkshires of Massachusetts is perfect for outdoor fun, cultural events, scenic drives, or a relaxing trip. It's a top New England destination with lots to see and do.

"The Berkshires offer a unique blend of culture, nature, and culinary delights that make it a truly captivating destination in Western Massachusetts."

Breweries, Wineries, and Cideries to Cap Off Your Visit

Exploring the Berkshires' natural wonders and cultural spots is rewarding. But nothing beats ending your day with the region's craft beverages. The Berkshires boast a wide range of breweries, wineries, and cideries. Each place offers a unique taste of the local area.

At Balderdash Cellars, wine lovers will find paradise. This winery sits among the hills, offering beautiful views. It's known for its wines that highlight the Berkshire region's best flavors. Visitors can enjoy tastings, tours, or just relax with a glass of their award-winning wine.

Craft beer fans will love the Berkshire's brewing scene. Check out Wandering Star Craft Brewery, Berkshire Brewing Company, or Big Elm Brewing. Here, you can try a variety of beers, from light pilsners to deep stouts. These breweries let you dive into the region's lively craft beer culture.

The Berkshire Cider Project is perfect for those who enjoy hard cider. They offer a range of ciders, from dry to sweet. It's a great place to explore different cider styles.

Whether you love wine, craft beer, or cider, the Berkshires have something for you. So, raise a glass and celebrate an amazing trip through this enchanting area.

The Massachusetts Museum of Contemporary Art (Mass MoCA)

Just a short drive from Boston, the Massachusetts Museum of Contemporary Art (Mass MoCA) in North Adams is a must-see for art lovers. It has an impressive 250,000 square feet of gallery space. Here, you can see everything from eye-catching ceramics to large-scale wall drawings and sculptures.

Mass MoCA is one of the biggest centers for contemporary art in the U.S. It offers a deep dive into the world of art. You can explore vast halls filled with works by famous and new artists. Each piece pushes the limits of what we think of as art.

But there's more than just art at Mass MoCA. The museum also hosts live music, theater, artist talks, and workshops. These events add to the excitement of visiting this cultural gem in the Berkshires.

If you're heading to the Berkshires, don't miss Mass MoCA. You'll be amazed by the art's scale and variety. And you'll leave with a new appreciation for creativity and innovation.

The Berkshire Museum

When you visit the Berkshires in Massachusetts, don't miss the Berkshire Museum in Pittsfield. It's a cultural gem with over 40,000 objects. You'll find fine art, natural science, and history all in one place. It's inspired by big names like the American Museum of Natural History and the Metropolitan Museum of Art.

The museum has something for everyone. You might love the art, be curious about science, or enjoy history. The Berkshire Museum is a top spot in the Berkshires. It lets you explore the area's history, see its natural beauty, and dive into art and creativity.

Visiting the Berkshire Museum is a must for anyone in the Berkshires. You'll be inspired, learn a lot, and have fun. This famous place offers a wealth of knowledge and culture that you won't want to miss.