15 Best Things To Do in The Berkshires

1. Tanglewood

Entertainment and Nightlife, Festivals

2 hours to Half Day

Tanglewood, nestled in the scenic Berkshire Hills of Massachusetts, offers a rich tapestry of activities for visitors. As the summer home of the Boston Symphony Orchestra, it is a cultural hub where music lovers can enjoy world-class performances in an outdoor setting. The Tanglewood Music Center hosts a variety of concerts, from classical symphonies to contemporary jazz, often featuring renowned guest artists. Beyond the music, Tanglewood's sprawling lawns and gardens provide a picturesque setting for picnicking, leisurely walks, and exploring nature trails. Families can enjoy the interactive Tanglewood Learning Institute, which offers workshops, lectures, and hands-on activities that delve into the world of music and the arts. For those seeking tranquility, the serene Stockbridge Bowl lake and nearby hiking trails offer opportunities for kayaking, swimming, and nature walks. Tanglewood seamlessly blends cultural enrichment with natural beauty, making it a perfect destination for both relaxation and inspiration.

2. Jacob's Pillow

Entertainment and Nightlife, Festivals

2 hours to Half Day

Jacob's Pillow, nestled in the picturesque Berkshires of Massachusetts, is a renowned dance haven offering a rich tapestry of experiences for visitors. As a premier dance festival, it presents world-class performances spanning diverse genres, from ballet and contemporary to hip-hop and traditional dance forms. You can immerse yourself in the vibrant atmosphere by attending these captivating shows in both indoor and outdoor venues, such as the historic Ted Shawn Theatre and the charming outdoor Henry J. Leir Stage. Beyond performances, Jacob's Pillow hosts interactive workshops and masterclasses led by acclaimed dancers and choreographers, providing a unique opportunity to refine your skills or simply enjoy the art of movement. The Pillow also features engaging talks, film screenings, and exhibitions that delve into dance history and culture. For those seeking a more leisurely experience, the serene grounds offer scenic walking trails, art installations, and picnic spots. A visit to the onsite Blake's Barn archives offers a fascinating glimpse into the Pillow's rich legacy. Whether you're a dance aficionado or a curious newcomer, Jacob's Pillow promises an inspiring, enriching adventure.

3. Monument Mountain

Free, Hiking, Sightseeing

2 hours to Half Day

Monument Mountain, located in the Berkshires of western Massachusetts, offers a picturesque natural retreat perfect for outdoor enthusiasts. Hiking is the primary activity, with several trails catering to different skill levels. The most popular route is the 2.5-mile loop to the summit, offering panoramic views of the Housatonic River Valley and the Taconic and Catskill Mountains. Along the way, you'll encounter diverse flora and fauna, making it a great spot for nature photography and birdwatching. The mountain is also steeped in literary history; it inspired writers like Nathaniel Hawthorne and Herman Melville, who once hiked here together. Interpretive signs along the trails provide insights into this rich cultural backdrop. Picnicking at designated areas near the trailhead is another enjoyable activity, allowing visitors to relax and soak in the serene environment. Whether you're hiking, birdwatching, or simply enjoying a peaceful picnic, Monument Mountain offers a refreshing escape into nature.

4. Mount Greylock

Hiking, Recreation, Monuments and Memorials, Sightseeing

Half Day to Full Day

Mount Greylock, the highest peak in Massachusetts at 3,491 feet, offers a plethora of outdoor activities and stunning natural beauty. Hiking is a primary draw, with trails ranging from easy walks to challenging climbs, including the famous Appalachian Trail that crosses the summit. The summit provides panoramic views of up to 90 miles, encompassing five states. For history enthusiasts, the Veterans War Memorial Tower at the summit honors Massachusetts soldiers and offers additional scenic vistas. Camping is available at nearby campgrounds, providing a base for exploring the area. In winter, the mountain transforms into a haven for snowshoeing and cross-country skiing. Birdwatchers and wildlife enthusiasts can enjoy the diverse flora and fauna, while photographers will find endless opportunities to capture the picturesque landscapes. Whether you're seeking adventure or tranquility, Mount Greylock delivers a memorable outdoor experience.

5. Clark Art Institute

Museums

2 hours to Half Day

The Clark Art Institute, located in Williamstown, Massachusetts, offers a rich blend of art, nature, and scholarly research. This world-class museum is renowned for its impressive collection of European and American paintings, sculptures, and decorative arts, featuring works by masters such as Renoir, Degas, and Homer. Visitors can explore the meticulously curated galleries, participate in educational programs, and attend special exhibitions that offer deeper insights into specific artists or art movements. Beyond the art, the Clark boasts a stunning 140-acre campus with walking trails, providing a tranquil setting for outdoor activities. The grounds feature installations by contemporary artists, making for a unique blend of nature and art. The Institute also houses a research library, which is invaluable for art historians and students. With a café serving delicious refreshments and a museum shop offering unique gifts, the Clark Art Institute ensures a fulfilling and enriching experience for all visitors.

6. The Mount

Historic Homes/Mansions, Tours

2 hours to Half Day

"The Mount," located in Lenox, Massachusetts, is a grand estate and former home of the renowned American author Edith Wharton. The estate offers a rich blend of historical, literary, and garden experiences. Visitors can tour the meticulously restored mansion, which showcases Wharton's exquisite taste in interior design and architecture. The guided tours provide fascinating insights into her life and works, reflecting her influence on American literature and design. The estate's formal gardens, inspired by European design, are perfect for leisurely strolls. They feature an Italianate walled garden, a French flower garden, and a lime walk, each offering a serene and picturesque setting. Art installations and seasonal events, such as outdoor theater performances and literary festivals, add to the cultural allure. Additionally, the café at The Mount provides a cozy spot to enjoy refreshments while overlooking the stunning landscape. Whether you're a literature enthusiast, history buff, or garden lover, The Mount offers a well-rounded, enriching experience.

7. Pleasant Valley Wildlife Sanctuary

Hiking, Sightseeing

2 hours to Half Day

Pleasant Valley Wildlife Sanctuary, located in Lenox, Massachusetts, offers a serene escape into nature with its diverse range of activities. Spanning over 1,000 acres, the sanctuary features more than seven miles of well-marked trails that meander through forests, wetlands, and meadows, providing ample opportunities for hiking and birdwatching. The scenic Pike’s Pond and Lenox Mountain trails offer breathtaking views and are perfect for nature photography. Visitors can explore the sanctuary’s educational programs, which include guided nature walks, wildlife observation, and seasonal workshops tailored for all ages. The sanctuary is home to a variety of wildlife, including beavers, otters, and an array of bird species, making it a haven for wildlife enthusiasts. The on-site nature center provides informative exhibits about local ecology and conservation efforts. Whether you're an avid hiker, a birdwatcher, or simply seeking a peaceful retreat, Pleasant Valley Wildlife Sanctuary offers a rich and immersive natural experience.

8. Jiminy Peak Mountain Resort

Amusement Parks, Skiing, Hiking, Recreation

Half Day to Full Day

Jiminy Peak Mountain Resort, nestled in the scenic Berkshires of Massachusetts, offers a wide array of activities for all seasons. In the winter, visitors can enjoy skiing and snowboarding on 45 trails, with options for all skill levels. The resort features a state-of-the-art snowmaking system, ensuring optimal conditions. For a unique experience, try night skiing under the lights. Summer transforms the resort into an adventure haven. The Mountain Adventure Park boasts an alpine slide, a mountain coaster, and scenic chairlift rides. Adrenaline seekers can tackle the Aerial Adventure Park, a treetop challenge course with various obstacles and zip lines. Hiking and mountain biking trails offer stunning vistas and encounters with local wildlife. Jiminy Peak is also an eco-friendly destination, powered significantly by its own wind turbine, Zephyr. With family-friendly activities, dining options, and comfortable lodging, Jiminy Peak Mountain Resort is an ideal year-round destination for outdoor enthusiasts.

9. Herman Melville's Arrowhead Museum

Museums, Free, Hiking

2 hours to Half Day

Herman Melville's Arrowhead Museum, located in Pittsfield, Massachusetts, offers a unique glimpse into the life and works of the renowned author Herman Melville. This historic farmhouse, where Melville lived from 1850 to 1863, is where he penned his masterpiece, "Moby-Dick." Visitors can explore the beautifully preserved home, featuring period furnishings and Melville's personal belongings, which provide a window into his daily life and creative process. Guided tours of the house offer rich insights into Melville's writing and the literary significance of "Moby-Dick," as well as his other works. The museum also hosts rotating exhibits, educational programs, and special events that delve deeper into Melville's legacy and 19th-century American literature. The picturesque grounds, with sweeping views of Mount Greylock, are perfect for a leisurely stroll, reflecting the natural beauty that inspired Melville's work. Whether you're a literature enthusiast or a history buff, Arrowhead Museum promises an enriching and immersive experience.

10. Ramblewild Adventure Park

Amusement Parks, Hiking, Recreation

2 hours to Half Day

Ramblewild Adventure Park, nestled in the scenic Berkshires of Massachusetts, is an exhilarating treetop adventure destination for thrill-seekers and nature enthusiasts alike. The park offers a variety of aerial courses that cater to different skill levels, featuring over 150 elements such as zip lines, rope bridges, and suspended obstacles. Visitors can challenge themselves on courses that range from easy to expert, all while enjoying breathtaking views of the forest canopy. The park's innovative design ensures that participants are safely harnessed and supervised by professional guides. In addition to the aerial adventures, Ramblewild emphasizes environmental stewardship and education. Guests can explore the surrounding forest trails, learn about sustainable forestry practices, and even participate in eco-tours that highlight local flora and fauna. Whether you’re seeking an adrenaline rush or a peaceful nature retreat, Ramblewild Adventure Park offers a unique blend of excitement and outdoor learning.

11. Massachusetts Museum of Contemporary Art

Museums

2 hours to Half Day

The Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams offers a rich array of experiences for art enthusiasts, families, and curious visitors alike. As one of the largest centers for contemporary visual and performing arts in the United States, MASS MoCA boasts expansive galleries filled with avant-garde installations, thought-provoking sculptures, and dynamic multimedia exhibits. You can explore long-term exhibitions from renowned artists like James Turrell, Sol LeWitt, and Jenny Holzer. MASS MoCA also features rotating exhibitions that highlight emerging and established artists from around the globe, ensuring that each visit offers something new. In addition to visual art, the museum hosts a robust schedule of performing arts events, including concerts, dance performances, and theater productions. The Kidspace area offers hands-on activities for younger visitors, making it a family-friendly destination. With its stunning industrial architecture, outdoor sculpture garden, and on-site dining options, a visit to MASS MoCA is an immersive cultural experience that stimulates both the mind and senses.

12. Norman Rockwell Museum

Museums

2 hours to Half Day

The Norman Rockwell Museum, nestled in the picturesque Berkshires of Stockbridge, Massachusetts, is a treasure trove of American art and culture. Visitors can immerse themselves in the world of Norman Rockwell, one of America's most beloved illustrators. The museum houses the largest collection of Rockwell's work, including iconic pieces like "The Four Freedoms" and "The Problem We All Live With." Engage with interactive exhibits that delve into Rockwell's artistic process and the historical context of his work. The museum also offers rotating special exhibitions, showcasing contemporary illustrators and other American artists. Wander through Rockwell's preserved studio, relocated to the museum grounds, to see where he created many of his masterpieces. The idyllic 36-acre property features beautiful gardens and scenic trails, perfect for a leisurely stroll. Educational programs, workshops, and family-friendly activities ensure a rich, immersive experience for all ages.

13. Naumkeag

Parks and Gardens, Historic Homes/Mansions

1 to 2 hours

Naumkeag, located in Stockbridge, Massachusetts, is a stunning Gilded Age estate renowned for its beautifully preserved mansion and exquisite gardens. Visitors can explore the 44-room "cottage," with its original furnishings, artwork, and decor, offering a glimpse into the lifestyle of the Choate family, who made Naumkeag their summer residence. The estate's gardens, designed by famed landscape architect Fletcher Steele, are a highlight, featuring the iconic Blue Steps, a series of fountain cascades flanked by deep blue railings and birch trees. Wander through the Afternoon Garden, Rose Garden, and Tree Peony Terrace, each offering unique horticultural delights and breathtaking views of the surrounding Berkshire Hills. Seasonal events and guided tours provide deeper insights into the estate’s history and design. Whether you're an architecture enthusiast, history buff, or garden lover, Naumkeag offers a serene and enriching experience in a picturesque setting.

14. Hancock Shaker Village

Historic Homes/Mansions

1 to 2 hours

Hancock Shaker Village, located in Pittsfield, Massachusetts, offers a rich, immersive experience into the world of the Shakers, a religious sect known for their simple living, architecture, and craftsmanship. Visitors can explore the meticulously preserved 19th-century buildings, including the iconic Round Stone Barn, which showcases innovative Shaker construction techniques. The village offers guided tours that delve into Shaker history, beliefs, and daily life, providing insights into their communal living and industrious spirit. Interactive exhibits allow guests to see Shaker furniture, textiles, and tools, highlighting their exceptional craftsmanship and design. Seasonal events and workshops on traditional crafts, farming, and cooking offer hands-on learning opportunities. The village's working farm features heritage breed animals and heirloom gardens, offering a glimpse into sustainable agriculture practices. With scenic walking trails, a farm-to-table café, and a well-stocked gift shop, Hancock Shaker Village provides a comprehensive and engaging experience for history enthusiasts and families alike.

15. Berkshire Botanical Garden

Parks and Gardens

1 to 2 hours

Berkshire Botanical Garden, nestled in Stockbridge, Massachusetts, offers a serene and educational escape into the world of horticulture. Spread across 24 acres, the garden features a diverse range of plant collections, including perennials, annuals, and an impressive arboretum. Visitors can explore themed gardens such as the Herb Garden, Rock Garden, and the Native Plant Garden, each showcasing unique flora and landscaping techniques. The garden is not just about passive enjoyment; it offers numerous interactive experiences. Throughout the year, educational programs, workshops, and lectures are available, catering to gardening enthusiasts of all levels. Seasonal events and art exhibitions further enrich the visit, providing cultural and artistic context to the natural beauty. Children can engage with nature through the Family Activity Center and various kid-friendly programs. Strolling along the well-maintained paths, you'll discover hidden sculptures and tranquil water features, perfect for reflection and photography. Berkshire Botanical Garden is a haven for nature lovers, offering both relaxation and inspiration.