The Getaway
20 Things to Do in The Berkshires

Tucked away in Western Massachusetts, the Berkshires boosts cultural wealth, natural splendor, and deep historical significance. The region offers diverse experiences, from the tranquil heights of Mount Greylock to the esteemed halls of famous museums. Whether you're passionate about history, art, or the outdoors, the Berkshires has something unique for you.


01 Discover the Norman Rockwell Museum

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

Stockbridge's Norman Rockwell Museum is a tribute to one of America's most cherished illustrators. The museum houses the largest collection of Rockwell's work. But it's about more than viewing art. The collection lets you step 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, to get a deeper understanding of his process. The museum also hosts special exhibitions and educational programs.


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 is the summer home of the Boston Symphony Orchestra. Here, music fills the Berkshire air under starlit skies, creating magical summer evenings. The lush lawns and stellar acoustics make it perfect for music lovers to enjoy classical, jazz, and contemporary performances. Beyond concerts, Tanglewood offers educational programs and chances 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 exhibits push the boundaries of creativity so visitors can experience 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 hard 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 is the highest point in Massachusetts. It's also 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 a physical journey that provides a chance to connect with nature and history. It has even been 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, is 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 photographed waterfalls in the region. The surrounding state park offers picnic areas and other trails, making it perfect 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, is a historic, elegant estate. With its beautiful gardens and preserved interiors, The Mount offers a glimpse into the Gilden Age's opulence. Visitors can explore the meticulously maintained rooms where Wharton penned some of her most famous works. The gardens, designed by Wharton herself, reflect her passion for landscape architecture. The Mount hosts literary discussions and outdoor theater events that celebrate Wharton's legacy.


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, is a testament to the Gilded Age's grandeur. This restored mansion offers insight into how wealthy Americans lived during an extravagant era. The mansion, now a museum and cultural center, features elaborate architecture and period furnishings, so you can see the original owner's lavish lifestyle. 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 is a culinary hotspot in the Berkshires. Great Barrinton's dining options showcase the region's farm-to-table ethos and culinary creativity. The town's vibrant food scene includes everything from gourmet bistros to international eateries. Great Barrington's farmers' markets and food festivals also highlight the area's commitment to fresh, local ingredients.


09 Farm-to-Table experiences

The region's commitment to farm-to-table dining is evident in restaurants and markets that offer fresh, locally sourced ingredients. This approach supports local farmers and producers while adding fresh flavors to dishes. Many restaurants in the Berkshires feature seasonal menus that reflect the region's produce.


10 Unique finds in Lenox Shops

Lenox is a picturesque town and shopping paradise. Downtown is full of boutiques and shops selling everything from artisan crafts to chic clothing. Shoppers can find hand-made jewelry, local art, antiques, and specialty items that reflect the Berkshires' artistic and cultural heritage. Charming streets and friendly shop owners contribute to an enjoyable experience for casual browsers and serious shoppers.


11 Seasonal splendor: Skiing and snowshoeing

The Berkshires isn't just a summer destination; it's a winter wonderland too. The region offers a variety of skiing and snowshoeing opportunities. Resorts and parks in the Berkshires have well-maintained trails and slopes for all skill levels. 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

Apple picking is a cherished tradition that lets you enjoy the crisp fall air and scenic beauty while indulging in the freshest apples you'll find anywhere. Orchards across the region open their doors so visitors can sample apples and enjoy activities like hayrides and corn mazes. Apple picking in the Berkshires is a way to connect with the land and celebrate the season's bounty.


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 is a former railroad track, now a paved trail, with stunning views of the Berkshires' landscapes. It's ideal for biking, walking, or enjoying the great outdoors. Stretching over 11 miles, the trail winds through picturesque towns, past lakes, and over streams. The trail is also a favorite among nature photographers. Birdwatchers, keep your eyes open for bald eagles, great blue herons, and woodpeckers.


14 Hancock Shaker Village insights

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

Hancock Shaker Village provides a window into America's unique history. Visit the museum for a glimpse into the Shaker lifestyle, known for its simplicity and craftsmanship. The village features restored buildings, gardens, and exhibits with furniture, tools, and art. Visitors can participate in workshops, enjoy guided tours, and partake in seasonal activities.


15 Boating and fishing on Pontoosuc Lake

Twilight view of Pontoosuc Lake in Pittsfield, Massachusetts.

Pontoosuc Lake is a recreational destination for anyone who loves boating, fishing, or simply having a picnic by the water. The lake is stocked with various fish, making it a popular spot for anglers. Its calm waters are ideal for kayaking and canoeing. The surrounding area has parks and trails for hiking and wildlife observation.


16 The Clark Art Institute's wonders

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

The Clark Art Institute is 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. The Clark's expansive grounds and outdoor sculptures make it perfect for leisurely walks. Inside, the galleries house masterpieces from the Renaissance to the early 20th century.


17 Berkshire's vibrant theater scene

From Shakespeare and Company's classic plays to the innovative performances at the Williamstown Theatre 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. You might want to plan your visit around one of these events.


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 and luxurious treatments for rejuvenation and peace. The spas in the Berkshires range from holistic wellness centers to luxurious resort spas. Each has 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

Local breweries and wineries dot the landscape, offering tastings of craft 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 on outdoor patios with scenic views.


20 Seasonal festivals and events

The Berkshires is alive with seasonal festivals and events. From music and food festivals in the summer to fall foliage celebrations and winter markets, events showcase the area's dynamic community 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 connection among residents and visitors alike.

As the seasons change, so does the Berkshires. You'll experience a different kind of beauty 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 never fails.


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