20 Things to Do in The Berkshires

Tucked away in Western Massachusetts, the Berkshires stand as a beacon of cultural wealth, natural splendor, and deep historical significance. This region, celebrated for its stunning landscapes and artistic spirit, offers a diverse array of experiences to suit every traveler. From the tranquil heights of Mount Greylock to the esteemed halls of its famous museums, the Berkshires serve as a sanctuary for those seeking a mix of outdoor adventure and cultural insight. Whether you're passionate about history, art, or outdoor pursuits, the Berkshires' allure lies not only in its picturesque scenery but also in its unique offerings for each visitor.


01 Discover the Norman Rockwell Museum

Stockbridge, MA / United States - Oct 20, 2017 - Landscape image of the Norman Rockwell Museum Brian Logan Photography /

In Stockbridge lies the Norman Rockwell Museum, a tribute to one of America's most cherished illustrators. This museum, housing the largest collection of Rockwell's work, isn't just about viewing art; it's about stepping into scenes that capture the essence of American life. Each painting tells a story, reflecting Rockwell's keen observation and poignant portrayal of everyday moments. Visitors can explore Rockwell's studio, preserved as he left it, providing a deeper understanding of his creative process. The museum also hosts special exhibitions and educational programs, making it a dynamic center for art lovers.


02 Tanglewood's musical evenings

Berkshires, MA, USA - July. 25. 2010: Summer concert at Ozawa Hall, Tanglewood Music Festival, Berkshires, state of Massachusetts, USA T photography /

Tanglewood, the summer home of the Boston Symphony Orchestra, isn't just a concert venue; it's an experience. Here, music fills the Berkshire air under starlit skies, creating magical summer evenings. The lush lawns and stellar acoustics make it a perfect spot for music lovers to enjoy classical, jazz, and contemporary performances in an idyllic setting. Beyond concerts, Tanglewood offers educational programs and a chance to see rehearsals, providing a comprehensive musical experience. It's a place where music aficionados can connect with the rhythms of nature and artistry.


03 Artistic haven at Mass MoCA

 Berkshires, MA, USA -September. 4. 2010: Massachusetts Museum of Contemporary Art (Mass MoCA) in North Adams, Massachusetts T photography /

Massachusetts Museum of Contemporary Art (Mass MoCA) isn't your typical art museum. Located in North Adams, it's a sprawling complex where contemporary art meets industrial space. The museum's ever-changing exhibits push the boundaries of creativity, offering visitors a unique blend of visual and performing arts. Mass MoCA also hosts festivals, artist talks, and interactive workshops, making it a hub for contemporary art lovers. Its vast space allows for large-scale and immersive installations that are rare to find elsewhere.


04 Scaling Mount Greylock

The top of Mount Greylock with War Memorial is the highest peak in the state of Massachusetts. It is located near the towns of Williamstown, Lenox and North Adams.

At 3,491 feet, Mount Greylock isn't just the highest point in Massachusetts; it's a hiker's paradise. The trails leading to the summit offer breathtaking views and a sense of tranquility. The Veterans War Memorial Tower at the peak provides panoramic vistas that stretch across the New England landscape. Hiking Mount Greylock is not only a physical journey but also a chance to connect with nature and history, as the area is rich in both natural beauty and historical significance, including being an inspiration for writers like Herman Melville.


05 The charm of Bash Bish Falls

Bish Bash Falls in Massachusetts in the Berkshire County

Bash Bish Falls, with its cascading waters set against a rugged backdrop, isn't just a waterfall; it's a natural masterpiece. The hike to the falls is as rewarding as the view itself, offering a serene escape into nature's embrace. Located near the border of Massachusetts and New York, Bash Bish Falls is one of the most picturesque and photographed waterfalls in the region. The surrounding state park also offers picnic areas and additional trails, making it a perfect destination for a day of exploration and relaxation in nature.


06 Historical journey at The Mount

Lenox, MA USA - June 24 2019 - The Mount. Edith Wharton's home from 1902 - 1911 Adam Gladstone /

The Mount, Edith Wharton's former home, isn't just a historic site; it's a journey into the past. This elegant estate, with its beautiful gardens and preserved interiors, offers a glimpse into the life of one of America's greatest writers and the Gilded Age's opulence. Visitors can explore the meticulously maintained rooms where Wharton penned some of her most famous works, and the gardens, designed by Wharton herself, reflect her passion for landscape architecture. The Mount also hosts literary discussions and outdoor theatre events, celebrating Wharton's legacy and the property's cultural significance.


07 Gilded age glamour at Ventfort Hall

 Berkshires, MA, USA -September.1. 2011: Ventfort Hall and Gilded Age Museum in Lenox, state of Massachusetts, USA T photography /

Ventfort Hall, an imposing mansion in Lenox, isn't just a historic building; it's a testament to the Gilded Age's grandeur. This meticulously restored mansion offers a fascinating insight into the lives of the wealthy during one of America's most extravagant eras. The mansion, now a museum and cultural center, features elaborate architecture and period furnishings, giving visitors a sense of the lavish lifestyles of its original inhabitants. Ventfort Hall also hosts exhibitions, concerts, and lectures, making it a vibrant center for Gilded Age history and culture.


08 Culinary delights in Great Barrington

Great Barrington, MA - October 17, 2016: Railroad Street lined with Traditional Brick Buildings and Colourful Shops and Restaurants. Great Barrington is Both a summer resort and home to Ski Butternut. Albert Pego /

Great Barrington isn't just a town; it's a culinary hotspot in the Berkshires. From cozy cafes to upscale restaurants, the town offers a diverse range of dining options that showcase the region's farm-to-table ethos and culinary creativity. The town's vibrant food scene includes everything from gourmet bistros serving local cuisine to international eateries offering flavors from around the world. Great Barrington's farmers' markets and food festivals further highlight the area's commitment to fresh, locally-sourced ingredients and innovative cooking.


09 Farm-to-Table experiences

The Berkshires aren't just about natural beauty; they're also a haven for foodies. The region's commitment to farm-to-table dining is evident in its numerous restaurants and markets, offering fresh, locally-sourced ingredients that turn meals into memorable experiences. This approach not only supports local farmers and producers but also ensures that diners enjoy the freshest and most flavorful dishes. Many restaurants in the Berkshires also feature seasonal menus, reflecting the region's changing landscapes and harvests.

10 Unique finds in Lenox Shops

Lenox isn't just a picturesque town; it's a shopping paradise. Its downtown area is lined with unique boutiques and shops, offering everything from artisan crafts to chic clothing, making it a perfect spot for those looking for something beyond the ordinary. Shoppers can find hand-made jewelry, local art, antiques, and specialty items that reflect the Berkshires' artistic and cultural heritage. Lenox's shopping experience is complemented by its charming streets and friendly shop owners, making it an enjoyable destination for both casual browsers and serious shoppers.

11 Seasonal splendor: Skiing and snowshoeing

The Berkshires aren't just a summer destination; they're a winter wonderland too. The region offers a variety of skiing and snowshoeing opportunities, with its scenic landscapes turning into a snowy playground for winter sports enthusiasts. Resorts and parks in the Berkshires cater to all skill levels, from beginners to advanced athletes, providing well-maintained trails and slopes. Beyond skiing and snowshoeing, the area also offers opportunities for ice skating and winter hiking, making it a premier destination for those who love the colder months.

12 Fall's apple picking tradition

woman hand picking an apple

In the Berkshires, autumn isn't just about colorful foliage; it's about apple picking. This cherished tradition is a perfect way to enjoy the crisp fall air and scenic beauty while indulging in some of the freshest apples you'll find anywhere. Orchards across the region open their doors to families and visitors, offering a range of apple varieties along with activities like hayrides and corn mazes. Apple picking in the Berkshires is more than just a harvest activity; it's a way to connect with the land and celebrate the bounty of the season.


13 Exploring the Ashuwillticook Rail Trail

Autumn view of the Ashuwillticook rail to trail in the Berkshire Mountains of Western Massachusetts.

The Ashuwillticook Rail Trail isn't just a path; it's a scenic journey. This former railroad track, now a paved trail, offers stunning views of the Berkshires' landscapes, making it ideal for biking, walking, or simply enjoying the great outdoors. Stretching over 11 miles, the trail winds through picturesque towns, past lakes and streams, and offers a safe and accessible way to explore the natural beauty of the Berkshires. The trail is also a favorite among birdwatchers and nature photographers, thanks to its diverse habitats and wildlife.


14 Hancock Shaker Village insights

An historical 18th century round barn, Hancock Shaker Village, Massachusetts, USA

Hancock Shaker Village isn't just a museum; it's a window into a unique American history. This living history museum offers a glimpse into the Shaker community's life, known for its simplicity, innovation, and craftsmanship. The village features restored buildings, gardens, and exhibits that showcase the Shakers' way of life, including their furniture, tools, and art. Visitors can participate in workshops, enjoy guided tours, and even partake in seasonal activities that bring the Shaker culture to life.


15 Boating and fishing on Pontoosuc Lake

Twilight view of Pontoosuc Lake in Pittsfield, Massachusetts.

Pontoosuc Lake isn't just a body of water; it's a hub for recreational activities. Whether you're into boating, fishing, or simply enjoying a picnic by the water, the lake offers a peaceful retreat amidst nature's beauty. The lake is stocked with a variety of fish, making it a popular spot for anglers, and its calm waters are ideal for kayaking and canoeing. The surrounding area, with its parks and trails, provides ample opportunities for hiking and wildlife observation, making Pontoosuc Lake a versatile destination for outdoor enthusiasts.


16 The Clark Art Institute's wonders

Williamstown, Massachusetts, USA The Clark Art Institute and gardens.

The Clark Art Institute isn't just an art museum; it's a cultural gem in the Berkshires. Known for its impressive collection of European and American art, the institute offers a serene environment where art and nature coexist harmoniously. The Clark's expansive grounds are perfect for leisurely walks, featuring outdoor sculptures and breathtaking views. Inside, the galleries house masterpieces from the Renaissance to the early 20th century, making it a haven for art enthusiasts and historians alike.


17 Berkshire's vibrant theater scene

The theater scene in the Berkshires isn't just entertainment; it's a cultural immersion. From Shakespeare and Company's classic plays to the innovative performances at the Williamstown Theater Festival, the region's theaters offer a diverse array of shows that reflect its rich artistic heritage. These venues not only showcase professional productions but also host community theater, children's programs, and educational workshops, making theater an integral part of the Berkshires' cultural landscape.

18 Relaxing retreats: Berkshire spas

A visit to the Berkshires isn't complete without experiencing its tranquil spas. These havens of relaxation blend natural settings with luxurious treatments, offering a perfect escape for rejuvenation and peace. The spas in the Berkshires range from holistic wellness centers to luxurious resort spas, each offering unique treatments inspired by the region's natural beauty. Visitors can indulge in massages, facials, and other therapies that incorporate local products like Berkshire botanicals.

19 Berkshire's craft breweries and wineries

The Berkshires aren't just about natural and cultural experiences; they're also a destination for craft beverage enthusiasts. Local breweries and wineries dot the landscape, offering tastings of uniquely crafted beers and wines. These establishments often use locally sourced ingredients, reflecting the region's agricultural heritage. Visitors can enjoy guided tours, learn about the brewing and winemaking processes, and relax in tasting rooms or outdoor patios with scenic views.

20 Seasonal festivals and events

The Berkshires aren't just a static destination; they're a region alive with seasonal festivals and events. From music and food festivals in the summer to fall foliage celebrations and winter markets, these events showcase the area's dynamic community spirit and rich traditions. The festivals often feature local artisans, musicians, and chefs, providing a platform for the Berkshires' talent and creativity. These events not only entertain but also foster a sense of community and connection among residents and visitors alike.

As the seasons change, so does the Berkshires, offering a different kind of beauty and experience with each visit. Whether it's the lush greenery of summer, the spectacular colors of fall, the serene snowscapes of winter, or the fresh blooms of spring, the Berkshires' charm is ever-present. It's a place where nature's allure, cultural depth, and historical richness converge, creating not just a getaway but a memorable journey into the heart of New England.


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