19 fun things to do in the Berkshires

A visit to the beautiful region of Western Massachusetts, known as the Berkshires, is a guaranteed hit for any kind of traveler. For nature lovers, the mountains and lakes provide an abundance of flora and fauna to discover, while outdoor enthusiasts will enjoy time spent hiking and kayaking. 

The list of things to do in the Berkshires is extensive. Luckily, the region is small enough that you can hit most of the items on this list. All you need to do is read this post, choose your favorite activities, map out your itinerary, and get going.

Oh, we almost forgot the most important task. Reserve one of our Boston van rentals to take you there!

1. Visit one of the Berkshires spas

Resorts in the Berkshires range from fancy to holistic, serene to indulgent. What do they all have in common? A slew of treatments that will relax even the most anxious of visitors. Melt your worries away with a deep tissue massage, body wrap, or both! After your treatment, decompress in the sauna or read a book in the relaxation room. 

Couples, friends, and families with older children are sure to benefit from a day of detox in any of the spas below.

  • Canyon Ranch in Lenox: This renowned wellness resort offers a range of treatments, fitness classes, and wellness programs. It’s ideal for those seeking a comprehensive experience.
  • The Spa at Cranwell in Lenox: Set within the Cranwell Resort, this spa offers a variety of treatments, including massages, facials, and body wraps. It also features an indoor pool, sauna, and steam room.
  • Kripalu Center for Yoga & Health in Stockbridge: While primarily known as a yoga retreat center, Kripalu also offers massages, facials, and Ayurvedic treatments. It perfectly combines wellness and mindfulness practices.
  • The Spa at Wheatleigh in Lenox: Located within the elegant Wheatleigh Hotel, this spa offers luxurious treatments, including massages, body scrubs, and beauty services. The serene setting and attentive service ensure a truly indulgent experience.
Source: HistoricHotels.org

2. See a show at Barrington Stage Company

If you appreciate performing arts and live theater, you must attend a show at the award-winning Barrington Stage Company. The theater company has produced well-known performances like The Diary of Anne Frank and Cabaret and is continuously introducing cutting-edge material.

Pro tip: Reserve tickets ahead of time to guarantee entry and secure the best seats.

Source: BarringtonStageco.org

3. Go hiking in the Berkshires

Take in the crisp air with a trek through the meadows, mountains, and forests that make up the beautiful Berkshires. The region is brimming with trails for every hiking level. Nature lovers and active explorers can’t miss a meander through the following paths:

  • Monument Mountain: Located in Great Barrington, this trail is known for its unique rock formations.
  • Mount Greylock: The highest peak in Massachusetts provides fabulous panoramic views from the summit and is also accessible by car.
  • Bash Bish Falls: This popular trail in Mount Washington State Forest leads to the highest waterfall in Massachusetts.
  • Kennedy Park: A network of trails in Lenox that wind through beautiful forests and meadows.
Source: Tripsavvy

4. See a concert at Tanglewood Grounds

This Boston Symphony Orchestra venue is the complete opposite of what you might expect. Instead of a dressy, indoor affair, Tanglewood Grounds is a casual, outdoor amphitheater boasting excellent acoustics where music enthusiasts gather to enjoy live classical shows under the stars. 

Tanglewood Grounds is by far one of the best things to do in the Berkshires in the summer. Make it memorable by packing a picnic blanket, a bottle of your favorite wine, and tasty snacks to munch on while soaking in the melodies created by Boston’s most talented musicians.

Source: BSO.org

5. Pick apples at Hilltop Orchards

Channel your inner farmer with a stroll through Richmond’s cutest apple orchard. Surround yourself with rolling hills and green fields while filling up a basket with fresh treasures to snack on throughout your road trip.

The 100-year-old family-run orchard also offers cider and wine tastings with a side of cider donuts, making it an ideal stop for families, friends, and couples looking for a unique and very local outing.

6. Tour a Berkshire museum

Get a feel for the art, history, and science that has shaped the Berkshire landscape with a visit to one of the fascinating museums located within a short drive of each other. Visiting a few Berkshires Museums is a great way to escape the heat of the summer or a winter freeze.

Art lovers shouldn’t miss:

  • The Clark Art Institute’s collection of European and American paintings, sculptures, and decorative arts
  • The Norman Rockwell Museum’s showcase of his iconic artworks capturing the essence of American life

History buffs will like:

  • The Berkshire Museum’s exhibition of the region’s past through a display of artifacts and interactive displays 

Science enthusiasts can check out:

  • The Berkshire Museum’s digital aquarium and planetarium

7. Take a drinking tour at Berkshire’s many wineries and breweries

The environment of the Berkshires doesn’t only lend itself to hikes and paddleboarding. Its fertile soil and cool climate are ideal for cultivating grapes and hops, so those of drinking age can spend a day taste-testing the local product. 

If you prefer wine, book a tour at:

  • Balderdash Cellars, known for small-batch wines made from locally sourced grapes
  • Furnace Brook Winery at Hilltop Orchards, known for great tastings and beautiful scenery

If beer is your thing, check out:

  • Elm Brewing’s variety of craft beers, made with locally sourced ingredients 
  • Shire Breu-Hous, famous for innovative brews and a cozy vibe
Source: Balderdash Cellars

8. Go camping

Disconnect with your phone, reconnect with nature. Whether it’s your first time or 50th, camping amongst the blue lakes and lush forests of the Berkshires is always a dazzling experience. Berkshires camping options are bountiful, but here are two to consider: 

  • October Mountain State Forest is a rustic experience offering secluded campsites nestled within the forest and opportunities for hiking, fishing, and wildlife observation. 
  • Pittsfield State Forest provides amenities like restrooms, showers, and picnic areas, along with plenty of hiking trails.

Cabin rentals are available, however, if you have your own camping gear, why not rent a van with Greenvans and bring it? There’s plenty of space to fit sleeping bags, portable stoves, and tents to ensure a comfortable camping experience.

9. See the sights at Pleasant Valley Wildlife Sanctuary

Local fauna are drawn to the diverse ecosystem of wetlands, meadows, and forests at Pleasant Valley. Set at the foothills of the mountains and known as a paradise for birds and beavers, wildlife lovers and hikers won’t want to miss a day at Pleasant Valley.

Consider signing up for a guided walk or popping into one of the family-friendly activities designed with kids in mind.

Source: Mass Audubon Society

10. Check out Hancock Shaker Village

The Shakers’ attempt to recreate Heaven on Earth is a wonderful way to spend a peaceful afternoon. Walk through herb and veggie gardens, explore historic 19th-century buildings, and learn to spin wool in The Discovery Barn. Families with young children will find the village especially worthwhile.

11. Go for a scenic drive

Roll along Route 7 for a taste of local life, passing by farms, antique shops, and charming villages. Catch fields of blooming wildflowers in the spring and colorful leaves in the fall. Starting in Sheffield, you can drive straight through 70 miles of scenery to Lenox or make stops to shop at boutique stores and farmer’s markets along the way.

Mohawk Trail is another option where you’ll drive alongside rivers, through forests, past museums, and by lots of great restaurants. If you’re looking for things to do in the Berkshires in the fall, this should be high on your list.

12. Visit the Berkshire Botanical Garden in Stockbridge

For a guaranteed pop of color and fragrance, visit the Botanical Garden’s 27 acres of unique flower displays. Check out the Children’s Discovery Garden if you’re traveling with little ones, or simply enjoy the nature and beauty of one of the oldest botanical gardens in New England.

Source: Berkshire Botanical Garden

13. Take a train ride on the Hoosac Valley Train

Sit back, relax, and watch the world go by on the historic Hoosac Valley Train. Railroad enthusiasts will appreciate the 1950s feel of this train experience while riding on 10 miles of restored track from Adams to North Adams. Learn about the area’s past from the onboard guides and check out the Lenox Station museum on Saturdays.

14. See Berkshires from above on a hot air balloon 

One of the most exhilarating vistas you can get in the Berkshires is the eagle’s eye view from a hot air balloon. Families, friends, and couples will find it to be an unforgettable experience and the traditional champagne toast at the end adds a lovely touch. Two reputable companies to check out are Berkshire Balloons in Hartford, CT, and Spirit Ballooning in Canaan, CT.

15. Go for a bike ride on the Ashuwillticook Rail Trail

Pack your bikes and enjoy a ride on the Ashuwillticook trail, once a former railroad corridor now converted into a 10-foot wide paved recreation path. The trail passes through the Hoosic River Valley and between Mount Greylock and the Hoosac Mountain Ranges. Wetlands flank much of the trail offering outstanding views of the scenery and abundant wildlife. 

16. Attend a cultural festival or event

The culture and entertainment scene in the Berkshires is vibrant, and festivals are held throughout the region from spring to fall. Fans of music, film, and opera will find much to celebrate here and should look at the city’s event calendar while planning a trip. 

Jacob’s Pillow Dance Festival is a particularly popular gathering that lasts two months in the summer. Watch incredible performances, dance your heart out, and take a masterclass — if you like to move, Jacob’s Pillow is for you!

17. Discover the Chesterwood estate and sculpture garden in Stockbridge

History and art buffs must visit the summer home of one of America’s foremost public sculptors, Daniel Chester French.

In the studio are original sketches of Abraham Lincoln which inspired French’s design of the Lincoln Memorial. The 122-acre grounds are full of flowers and sculptures, and a nice outdoor alternative to hiking in the Berkshires.

Source: Enchanted Garden Design

18. Take a tour of Ventfort Hall Mansion and Gilded Age Museum 

Walk directly into the opulent Gilded Age on a tour through J.P. Morgan’s sister’s Elizabethan-style mansion, built in 1893. Explore a pivotal period of U.S. history where life, industry, and society shifted significantly, changing the country’s future forever.

Pro tip: Check their website for any comedy shows or trivia nights taking place at Ventfort Hall!

19. Shop and dine in Great Barrington

When you’re ready to decompress from the many hikes, museums, and train rides abundant in the beautiful Berkshires, head to Great Barrington. The walkable, almost-urban hub is oozing with boutique shops and farm-to-table dining.

Spend the night in a historic inn, sip on a cappuccino in a cozy cafe, hike a mountain, peruse souvenirs, and taste local wine at a funky restaurant. This lively town is the perfect ending to an unforgettable visit to Western Massachusetts!

Source: The Berkshire Edge

How to enjoy Berkshire all year ‘round

There are so many things to do in the Berkshires that we think it’s best to divide the list by season. From skiing to apple picking and everything in between, you’ll have plenty of activities to keep anyone, of any age, smiling all day and night! 

  • Things to do in the Berkshires in the spring:
    • Go for a hot air balloon ride at sunrise
    • Walk the gardens and visit the art studio at Chesterwood Estate
    • Stroll through the Berkshire Botanical Garden
  • Things to do in the Berkshires in the summer:
    • Attend an outdoor concert at Tanglewood
    • Hike Mount Greylock, the state’s highest peak
    • Dance the night away at Jacob’s Pillow Dance Festival
  • Things to do in the Berkshires in the fall:
    • Drive through bright fall foliage on the Mohawk Trail
    • Harvest your own apples at Hilltop Orchard
    • Look for beavers at Pleasant Valley Wildlife Sanctuary
  • Things to do in the Berkshires in the winter:
    • Visit the many art museums in the area
    • Sip local craft beer in a cozy taproom
    • Ski by day, shop, and dine by night in Great Barrington

Looking to continue your snowy adventure? Make sure to check out our winter road trip ideas.

Road trip to the Berkshires with Greenvans

There’s no doubt that this part of New England is stunning. The towns are charming, the drinks are flowing, and the museums are state-of-the-art. Above all, the landscapes are like no other in the USA. 

Don’t miss a thing — rent a passenger van and head out for an easy, spectacular road trip through the rolling hills and mountain peaks of Western Massachusetts. No matter when you decide to go on a trip to the Berkshires, Greenvans will get you there in comfort and style.


The quality & service you’re looking for is right here.