24 Best Things to Do in the Berkshires, Massachusetts

By VacationIdea Staff on October 26, 2022 - Updated

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Located in the beautiful mountains of Western Massachusetts, The Berkshires is a popular vacation destination within easy traveling distance of New York City, Boston and Albany. The area is well known for great outdoor recreational activities as well as a thriving farm-to-fork restaurant scene and a good helping of arts and culture. There are some excellent museums and art galleries to admire and when you need some exercise you can head for the hills to enjoy great hiking, mountain biking and canopy tours. In winter, the area is a popular skiing destination. For additional information, you can visit berkshires.org.

We recommend that you call the attractions and restaurants ahead of your visit to confirm current opening times.

1.The Arrowhead Museum

The Arrowhead Museum in Pittsfield is a must-see attraction for anyone who has been enchanted by the novel Moby Dick. The museum is housed in the former home of the book’s author, Herman Melville and is sometimes also referred to as the Herman Melville House. The interior of the house has been carefully restored to reflect the daily life of the author when he was working on the book back in the 1800’s. You can join a guided tour of the house and gardens to learn more about the history of the home and the author or set off on a self-guided tour of the nature trail.

Herman Melville’s Arrowhead, 780 Holmes Rd, Pittsfield, MA 01201, Phone: 413-442-1793

2.Monument Mountain Reservation

The remarkable view from the summit of Squaw Peak is what draws thousands of hikers to Monument Mountain Reservation every year. The reservation has several loop trails which will lead you to the 1,642-foot summit where you will be rewarded for your efforts by outstanding views of the Housatonic River Valley and the southern Berkshires. None of the trails exceed three miles in length but all of them are quite steep and hikers need to be reasonably fit to cope with the 720-foot gain in elevation. First-timers should consider using the 1.5-mile Indian Mountain Trail (the least steep and most interesting trail) while confidently fit hikers can opt for the 0.8-mile Hickey Trail which offers the most direct but steepest ascent. Monument Mountain is a Trustees of Reservations property.

Monument Mountain Reservation, Route 7, Great Barrington, MA 01230, Phone: 413-298-3239

3.Berkshire Botanical Garden

The beautiful Berkshire Botanical Garden is the ideal place to spend a few hours enjoying the year-round showcase of beautiful flowering plants and trees. The garden was started back in 1934 and covers more than 15 inspirational acres. The huge garden is divided into several separate areas each of which displays a different and unique seasonal palette. Some of the highlights your can explore include the Pond Garden, the Daylily Walk, the historic Herb Garden and the Children’s Discovery Garden. There are three glass houses, an education center and several galleries. One of the best ways to explore the garden is to join a free guided tour at 11am daily from June to September.

Berkshire Botanical Garden, 5 West Stockbridge Rd, Stockbridge, MA 01262, Phone: 413-298-3926

4.Berkshire Museum

The Berkshire Museum has been stimulating the minds of thousands of adults and children for over 100 years and remains a fascinating attraction for both locals and visitors. The main focus of the museum is to demonstrate the connections between science, history and the arts through its many permanent and temporary exhibitions. Highlights of your visit to the museum will include the inter-active Curiosity Incubator and Lab 102, the Window on the World exhibition, the Aquarium and the Berkshire Backyard which features all the little critters to be found in the area. The museum also hosts a full program of fun educational activities for children.

Berkshire Museum, 39 South Street (Route 7), Pittsfield, MA 01201, Phone: 413-443-7171

5.Bousquet Ski Area

Bousquet Mountain Ski Area is a must-visit attraction for all winter visitors to the Berkshires. The popular ski area includes a large variety of down-hill skiing or boarding slopes for all levels of expertise, including a couple of really tricky slopes for experts only. Regardless of your skiing ability you will be able to find a ski program to suit you and the other members of your family. Everything you need for some fun in the snow can be rented on site, either for a day or two or for the entire season. If you enjoy snow tubing you can have hours of fun on the multi-lane 450 foot snow tubing hill which has a wonderful magic carpet which will effortlessly whisk you back up to the top for another ride.

Bousquet Mountain Ski Area, 101 Dan Fox Drive, Pittsfield, MA 01201, Phone: 413-442-8316

6.Catamount Aerial Adventure Park

For a day of thrilling outdoor adventures you can make your way to the Catamount Aerial Adventure Park in South Egremont. Provided you have a good head for heights you are in for an exhilarating aerial adventure which includes navigating the forest canopy on a series of 12 courses which have been set up between 170 aerial platforms, linked by a series of cables, ropes and zip-lines. The course is suitable for the whole family (minimum age 7 years – 48 inches minimum height) and there are designated areas for beginners to find their feet. As your confidence improves you can move to the more challenging courses which require greater balance and strength to navigate.

Catamount Aerial Adventure Park, State Highway 23, South Egremont, MA 01258, Phone: 518-325-3200

7.Catamount Ski Area

Perfect for families with differing levels of skiing prowess, Catamount Ski Area stands out as offering a very diverse network of skiing and boarding trails which vary from super easy to super steep and challenging. Children and beginners can find their ski legs on the Snowsport Learning Area which is located close to the Base Lodge. The next step for most visitors will be the Meadows complex which offers a variety of relatively easy open slopes that will suit most families, while experts and dare-devils will opt to take on the Upper and Lower Sidewinder Trails and the double-diamond Lynx and Catapult Trails. Both private and group lessons are available to ensure you have the time of your life.

Catamount Ski Area, State Highway 23, South Egremont, MA 01258, , Phone: 518-325-3200

8.Chesterwood Museum

Fabulous Chesterwood is an historic artist’s retreat which is essential viewing for any art-loving visitors to the Berkshires. Home to the famous American sculptor Daniel Chester French, whose imposing works are dotted all around the US and include the Abraham Lincoln sculpture at the Lincoln Memorial, the museum is still providing inspiration for modern-day artists. Visitors are able to tour the historic house, studio and gardens and admire hundreds of marble and bronze sculptures on display. In addition, there are some hands-on activities for younger visitors, a museum shop and a beautiful woodland walk. The museum is open from May to October.

Chesterwood Museum, 4 Williamsville Rd, Stockbridge, MA 01262, Phone: 413-298-3579

9.The Clark Art Institute

Dedicated to furthering public understanding and appreciation of art, The Clark is a must-visit attraction to add to your Berkshire itinerary. The Clark is the custodian of a very impressive permanent collection of European and American art which spans the period from the Renaissance to the early 20th century. You will find a good representation of the works by the French Impressionists and several prominent American artists including John Singer Sergeant and Winslow Homer. The best way to broaden your knowledge of the collection is to pick up a multi-media guide at reception and enjoy the experience at your own pace. Check their website to see if your visit will coincide with one of their educational programs and workshops.

The Clark, 225 South Street, Williamstown, MA 01267, Phone: 413-458-2303

10.Hancock Shaker Village

The Hancock Shaker Village was established as far back as 1783 and today offers visitors a rare glimpse of how the original Shaker immigrants went about their daily life. Your day at the village will include visiting up to fifty room-setting exhibits which preserve and showcase much of the simple textiles, furniture and house-hold goods which were made by the early Shaker residents. A tour of the village will include a visit to the Round Stone Barn, the Farm and Gardens and talks about the innovation and simple Shaker life-style. You can start your visit by viewing an orientation video and then explore at your own place using a Walking Tour Guide. Remember to pay a visit to their Farm-to-table restaurant and store before you leave.

Hancock Shaker Village, 34 Lebanon Mountain Rd, Hancock, MA 01237, Phone: 413-443-0188

11.The School at Jacob's Pillow

Jacob's Pillow is all about dance, dance and more dance. The center has achieved world-wide recognition as a premier center of dance which offers tuition in various dance forms and hosts an annual Festival which attracts thousands of people to the Berkshires. The Pillow is housed in a National Historic Landmark and offers many activities throughout the year – you can enjoy exploring at your own pace with the assistance of a self-guided tour map. If you are planning to visit during the Dance Festival you are in for a wonderful treat; expect the chance to see up to 200 free performances by more than 50 dance companies as well as several inspirational talks and events.

Jacob's Pillow, 358 George Carter Rd, Becket, MA 01223, Phone: 413-243-9919

12.Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort is easily accessible from New York City or Boston is less than three hours, making this an ideal destination for a fun-filled family vacation at any time of the year. When the snows turn the mountain into a winter-wonderland you can enjoy skiing and snowboarding for all skill levels, on-site rental equipment and lessons for both beginners and expert skiers. In summer you can explore hiking and mountain-biking trails, enjoy the thrilling rides at the Mountain Adventure Park or hone your aerial wire skills at the Aerial Adventure Park which offers six separate elevated courses and includes three exciting zip-lines. There is a variety of lodging options available including vacation homes and self-catering apartments.

Jiminy Peak Mountain Resort, 37 Corey Rd, Hancock, MA 01237, Phone: 413-738-5500

13.Onota Lake

Lovely Onota Lake covers over 600 acres within the city limits of Pittsfield. Along the eastern shore of the lake you will find Burbank Park which offers both locals and visitors a 150-acre recreational area where you can enjoy walking, picnicking and all kinds of boating. You can bring along your own boat to launch at the free public launching area or rent a canoe, kayak or motor boat at the Onota Lake Livery on Peck’s Rd. Burbank Park also has a popular swimming beach (Lifesavers on duty during July and August) and a walking path which meanders along the shores of the lake. Fishing is rumored to be very good and fishing derbies are held all year round, including ice-fishing in winter.

Onota Lake, Lakeway Drive, Pittsfield, MA 01201

14.Pleasant Valley Wildlife Sanctuary

Operated by Massachusetts Audubon, the Pleasant Valley Wildlife Sanctuary is a very pleasant place to spend a few hours walking, hiking and wildlife watching. Pleasant Valley covers more than 1000 acres of forests, wetlands and meadows and has over seven miles of hiking trails including a challenging hike which takes you to the summit of Lennox Mountain. You can often observe beaver activity from the observation platform at Pike’s Pond and if you visit in summer you can join a canoe excursion on the Housatonic River. Pleasant Valley hosts Summer Camp for younger outdoor enthusiasts to encourage wildlife observation and active outdoor activities.

Pleasant Valley Wildlife Sanctuary, 472 West Mountain Rd, Lenox, MA 01240, Phone: 413-637-0320

15.MASS MoCA

The Massachusetts Museum of Contemporary Art is a Mecca for patrons of the arts in the Berkshires and is really deserving of a place on your vacation itinerary. The Museum is devoted to involving the public in all art forms including painting, photography, sculpture, performing arts and just about anything else that could be classified as art. To enhance your visit to the museum you can join one of the daily guided tours (check their website for seasonal times) or you could just explore at your own pace. Children get the chance to release their creativity at the Kidspace hands-on studio and the Artbar while adults can attend a variety of educational workshops.

MASS MoCA, 1040 MASS MoCA Way, North Adams, MA 01247, Phone: 413-662-2111

16.Mount Greylock State Reservation

Visiting the summit of the 3,489-foot Mount Greylock will see you standing on the highest point in Massachusetts. If you choose a really clear day the views are amazing and you could be able to see as far as 90 miles over five states. If you love views but hate hiking there is good news – you can drive all the way up to the summit during the summer months and if you feel particularly energetic you can climb up to the top of the Massachusetts Veteran’s Memorial Tower. Hikers can follow several trails to the top of the mountain – the shortest route takes around 90 minutes but most people opt for a comfortable half or full-day hike. If you visit during the autumn you will have the added bonus of spectacular fall foliage.

Mount Greylock Reservation, 30 Rockwell Rd, Lanesborough, MA 01237, Phone: 413-499-4262

17.Natural Bridge State Park

The Natural Bridge State Park is a wonderful destination for all nature lovers and geology enthusiasts. Here you will be able to see the only natural white marble arch in North America which was formed by the remarkable forces of a receding glacier over 13,000 years ago. The natural bridge or arch spans a remarkable 60-foot gorge through which you can see the Hudson Brook twisting and tumbling. The best way to learn about the formation of the arch and surrounding gorge is to join a guided tour. If you prefer to explore at your own pace there are several easy family-friendly trails and a picnic area.

Natural Bridge State Park, McAuley Rd, North Adams, MA 01247, Phone: 413-663-6392

18.Naumkeag

Lovely Naumkeag, a Trustees of Reservations property, is one of the few surviving examples of a Gilded Age country estate to have survived intact. The extravagant 44-room “cottage” was built in 1884 to serve as a family summer retreat for the Choate family. Besides admiring the remarkably preserved single-shingle home which still contains all the original furnishings and décor, you can also tour the superb gardens, which were laid out over a period of thirty years. The beautiful property is open to the public between April and October each year – entry to the home is by guided tour only. The gardens can be explored at your own pace and highlights include the recently-restored glasshouse, the Rose Garden, Chinese Garden and Afternoon Tea Garden.

Naumkeag, 5 Prospect Hill Rd, Stockbridge, MA 01262, wPhone: 413-298-8138

19.Norman Rockwell Museum

Art enthusiasts can spend an interesting and informative couple of hours admiring the wonderful collections of one of America’s greatest artist/illustrators at the Norman Rockwell Museum. The museum is home to many of the artist’s original works and the wonderful permanent collection numbers over 900 original paintings and drawings. Rockwell spent the last years of his life in Stockbridge and bequeathed his Stockbridge studio to the museum before he passed away; today you can visit the artists’ favorite studio which forms part of the museum to see where many of his best works were created. The museum regularly hosts special exhibitions which showcase the different periods in the artists life.

Norman Rockwell Museum, 9 Glendale Rd, Route 183, Stockbridge, MA 01262, Phone: 413-298-4100

20.Pittsfield State Forest

Pittsfield State Forest is an easily-accessible 11,000 acre forested recreational area where you can spend a couple of hours or a few days getting back to nature. Outdoor enthusiasts can enjoy many activities in the forest including horse-back riding and exploring some of the 30 miles of hiking trails. Mountain biking is also popular and Berry Pond offers canoeing, kayaking, swimming, boating and fishing. If you would like to stay overnight you can pitch your tent at one of three basic campgrounds and enjoy great star gazing after dark. In addition, there are 16 miles of trails for off-road vehicles and in winter you can enjoy snowmobiling and cross-country skiing.

Pittsfield State Forest, 1041 Cascade St, Pittsfield, MA 01201, Phone: 413-442-8992

21.Ski Butternut

Ski Butternut is a family-friendly ski destination located on Warner Mountain in The Berkshires. The ski resort covers over 110 skiable acres, of which no less than 20% are suitable for children and beginners. To be precise, you can choose from eight beginner and intermediate slopes while more experienced skiers have 6 challenging slopes to explore. The ski runs are serviced by 11 ski lifts and lessons, equipment hire, refreshment stations and accommodation is available on site. The Twisted Terrain Park offers a thrilling obstacle course run while the Cruiser Progression Park offers a toned-down course with smaller boxes, rails and jumps. There is also a seasonal eight-lane tubing center with Magic Carpet lift.

Ski Butternut, 380 State Rd, Great Barrington, MA 01230, Phone: 413-528-2000

22.The Mount (Edith Wharton’s Home)

Edith Wharton was one of America’s greatest woman authors and a great admirer of art and architecture. Her Berkshires home, The Mount, was one of her most prized accomplishments and every detail of the architecture, décor and gardens was personally designed by the author. Today you can learn all about the life and times of Edith Wharton and the superb house she designed as you join a guided tour of the house and gardens, a Backstairs Tour or even the popular Ghost Tour. In addition to admiring the home and gardens you can explore several walking trails, have a snack at the Terrace Café and buy a souvenir at the Bookstore.

The Mount, 2 Plunkett Street, Lenox, MA 01240-0974, Phone: 413-551-5111

23.Ventfort Hall Mansion and Gilded Age Museum

Celebrating the Jacobean Revival-style of architecture, Ventfort Hall is an imposing mansion which dates back to 1893, during the hey-day of the Gilded Age. (At that time about 75 opulent “cottages” were built in the Lenox area as summer homes for wealthy Americans). Today the partially restored mansion (which has 15 bedrooms, 13 bathrooms and several elegant reception rooms) is home to the Museum of the Gilded Age and is open to the public all year round. You can learn all about the Gilded Age and admire the beautifully restored rooms of the mansion by joining a guided tour (offered daily).

Ventfort Hall Mansion and Gilded Age Museum, 104 Walker Street, Lenox, MA 01240, Phone: 413-637-3206

24.Williams College Museum of Art

Located on the campus of Williams College, the Williams College Museum of Art (WCMA) is a vibrant artistic hub where students come to learn about all aspects and disciplines of art. The museum has a large and eclectic collection of over 14,000 art works and at any one time you will be able to admire works from several different eras and in several different media. The museum regularly hosts special exhibits (which are not restricted to the visual arts but may include performing arts, dance and more) which set out to encourage visitors to think a little differently about the influence of art and museums in our daily lives.

Williams College Museum of Art, 15 Lawrence Hall Dr, Williamstown, MA 01267, Phone: 413-597-2429