10 Ways to Have Fun in the Berkshires in Massachusetts

The Berkshires, comprised of over 30 towns and two cities, is located in the most western part of Massachusetts. It includes towns ranging from Sheffield and Great Barrington in the southern part of the state, bordering Connecticut, to the towns of Wiliamstown and North Adams in the northern part of the state, bordering Vermont. The region is popular year round for outdoor activities, performing arts venues, galleries, museums, and historic homes and landmarks. The Berkshires have been home well known figures such as authors Edith Wharton, Nathaniel Hawthorne, Herman Melville, and activist W.E.B. DuBois. Dubbed the “Inland Newport” during the Gilded Age of the 20th century, the area became well known for its over 75 estates, in addition to its thriving farming industry.  Today, there are many spots to learn about the important history of the area and many preserved outdoor spaces to enjoy nature all year long.

A great place to start your planning for a visit is Berkshires.org. The website is well organized with sections on lodging, dining, and activities. Be sure to check out the calendar section before you go for special events and seasonal fun, and the “10 Great” tab for several themed lists by various ages and interest. Check here for guides on Stockbridge, Lenox, and Pittsfield. We found the area to be very family friendly and enjoyed the following spots:

10 Activities for Families in the Berkshires:

1. Take a hike! The Berkshire Natural Resources Council includes over 55 miles of hiking trails across more than 12,000 acres. Visitors can hike, bike, swim, fish, ski, boat, and picnic.  Hiking trails stretch from Great Barrington up to North Adams.  Hikers can find an index of over a dozen trails, ranked by level of difficulty, and descriptions including types of recreation here.  One popular spot is Olivia’s Outlook in Lenox, at the center of the 734 acre Yokun Ridge. Olivia’s Overlook is the spot is also the trailhead for several trails, all of which are under three miles round trip. More information on the trails here. Monument Mountain in Great Barrington is another popular spot. Overseen by the Trustees, the 503 acre spot has amazing views at the summit of the mountain. More information on trail maps and where to park here. The highest point in the Berkshires (and Massachusetts) is Mount Greylock- we plan on attempting some of the more low key hikes sometime in 2021. More information here.
Kids will love: the ease of the trails- most of them are under 2 miles round trip.
Travel Tips: There is a small parking lot (space for 10 cars) directly overlooking the stunning view of the Stockbridge Bowl. Cross the (very busy) street to the kiosk with trail maps.

2. Tour the private home of the first female Pulitzer Prize winning American author Edith Wharton at her home, The Mount, in Lenox. The 49 acre property includes the main mansion, stables, gardens, and hiking trails. The English style country house has both French and Italian inspired architectural elements and furnishings. Tours through the home and gardens are self-guided; there are docents stationed throughout the home to answer questions and placards in each room that share personal stories of the Whartons and explain the period décor and furnishings.
Kids will most enjoy running through the Lime Walk, searching for hidden “dogs”, and checking out the old fashioned kitchen tools. 
Travel Tips:

• The grounds, gardens, and Terrace Cafe are open to the public without charge. Self-guided tours of the interiors of the home  require tickets. Children receive FREE admissions. Advanced reservations are required- check here for information on reserving tickets and hours of operation.
• Guests must park, check in at the shed, and then walk ½ of a mile to the home. Guests with handicap placards are able to drive directly to the home and park in front.
• The mansion is handicap accessible with an elevator. Strollers are not allowed in the mansion. Restrooms are located on the first floor of the house and in the stable.
• The Terrace Café (open seasonally) is located on the second floor overlooking the gardens and is accessible through the dining room and by the side entrance of the mansion. The Cafe sells drinks, snacks, and lunch items and guests are permitted to purchase items and picnic on the grounds.
• Families should plan on spending one hour in the main house and another one hour exploring the grounds and gardens.

Read our full post on The Mount here.

3. Pretend to be Gilded Age heir Sara Morgan at her summer home Ventfort Mansion in Lenox. Financier JP Morgan gifted his sister Sara the equivalent of three million dollars, which she used to purchase the property and build the mansion in the late 1800s. Once almost 30 acres, parts of the grounds were sold over the year and private homes were built on the front lawn. The back lawn remains intact.  Begin in the library, which has a slideshow of biographical information on the Morgan family and various subsequent owners of the mansion. The mansion was placed on the National Register of Historic Places in the 1990s and opened to the public for tours in 2000.
Kids will most enjoy touring some of the 15 bedrooms and 13 bathrooms, seeing the replica dining room, choosing a favorite butterfly in the Butterfly Room, and the children’s room with an authentic period dollhouse, rocking horse, books, and toys.
Travel Tips: The mansion is open seven days a week for self guided tours and daily guided tours are also offered- check here for more information; restrooms and a small gift shop are located on the first floor near the entrance; the second floor is handicap accessible; strollers are not allowed in the mansion; hold on to toddlers; many breakable furnishings are within easy reach; plan on an hour to explore the mansion.

4. Catch a show at one of several performing arts centers.  The Berkshires are most famous for the Tanglewood Music Festival in Lenox, the summer home of the Boston Symphony Orchestra (read about our visit to the BSO here). But there’s also Shakespeare & Co. in Lenox, Jacob Pillow’s in Becket, and the Mahaiwe Performing Arts Center in Great Barrington, which offers a wide variety of performances, lessons, and workshops in music, dance, and theater.
Kids will most enjoy the family friendly events of Tanglewood- check here for the annual calendar.
Travel Tips: Tickets for popular events sell out quickly- usually the day they go on sale. Be sure to keep an eye out for release dates. Find out for more information for:

• Tanglewood
• Shakespeare & Co.
• Mahaiwe PAC
• Jacob’s Pillow

5. Frolic through dozens of gardens at the Berkshire Botanical Garden in Stockbridge. The 20+ acre garden is spread out over both sides of Route 102 and includes everything from culinary, herb, and vegetable gardens to rose gardens, a pond garden and more! There are weekly workshops, classes, and family activities and plenty of seasonal celebrations.
Kids will most enjoy the Children’s Discovery Garden, Fairy Garden, and Lucy’s Garden.
Travel Tips: The Garden is open every day through mid October and offers free admission in the winter. Check here for more information and advanced ticket sales; restrooms are located in the Center House and Education Center. bring a stroller for the toddler crew and everyone should wear closed toe shoes; plan on spending two hours to fully explore all the gardens, more if you linger in some areas.
Read our full post here.

6. Learn about the life of famed artist Norman Rockwell at his namesake museum in Stockbridge. The 36 acres property includes an indoor museum, outdoor sculpture garden (created by Rockwell’s son Peter), and Rockwell’s studio that was moved to the property. The museum has the largest collection of original art by Rockwell, including a display of 323 framed covers of the Saturday Evening Post that showcased Rockwell’s works, introductory videos that briefly narrate Rockwell’s life and several art galleries. 
Kids will most enjoy choosing a favorite Post cover and following the path of the sculptures. There is also a River Path on the property to let kids run free and burn off energy.
Travel Tips: The museum is currently closed on Tuesdays- more information on hours and admissions here; the studio is open from May through October; kids, teachers, and active and retired military all receive FREE admission; bring the stroller for the toddler crew. The museum and studio are handicap accessible; restrooms are located on both floors and a gift shop is located near the entrance to the museum; the Runaway Cafe is open for lunch each day- more information here; plan on 2 hours to explore the museum and grounds with children.

7. Check out the fishes, gems and minerals, and at the Berkshire Museum in Pittsfield. Opened in 1903 to showcase the private collection of Zenas Crane, the museum includes exhibits on art, sciences, and natural history with exhibits featuring gems and minerals, wetland and woodland birds, mammals, and a large interactive exhibit on Innovation.
Kids will most enjoy the lower level aquarium and Animals of the World diorama exhibits. 
Travel Tips: The museum is undergoing a major facelift and some exhibits may be closed. Timed tickets are necessary for 2020- check here for more admission information and hours. Kids, teachers, and active and retired military all receive FREE admission; parking is available in nearby lots and on the main streets- check here for more information; no need for a stroller- kids won’t want to sit still! The museum is handicap accessible; a coat room, restrooms, and a gift shop are all located near the entrance; plan on 90 minutes- two hours to fully explore all exhibits.

8. Learn about the daily life of the Shakers at Hancock Shaker Village in Pittsfield. The oldest working farm in the Berkshires of western Massachusetts, the Village was originally home to the Shaker community from the late 1700s until 1959. It reopened in 1961 as a museum that includes over 22,000 original artifacts and a research library. The 750 acre complex has a 20 acre working farm, 20 buildings with live interpreters, a massive garden with a very popular Community Supported Agriculture (CSA), and tons of hiking trails, meadows, and woodlands that abut the Pittsfield State Forest.
Kids will most enjoy seeing all the animals up close, trying hands on chores in the Discovery Barn (currently closed in 2020 due to pandemic restrictions), and exploring some of the 20 buildings to see what daily life was like.
Travel Tips: Wear sneakers and bring the stroller for the toddler crew. There are only a couple of places to sit throughout the complex and the one way path is paved with grass, gravel, or dirt; the Village is traditionally open from April through October, with special events on weekends in November and December. Check here for the calendar and times and check here for a list of special tours; an audio tour is available and download the app for plenty of trivia about the Shaker lifestyle and beliefs.; check in at the Welcome Center to purchase tickets (check on promotions and discounts here), use restrooms (the only accessible ones on property), and visit the Shaker Mercantile Shop, which offers a wide selection of children’s apparel, books, and toys; housewares; stationery; and reproduction Shaker style furniture; plan on two to three hours to fully explore the entire complex. Children might want to spend more time in the Discovery Barn and avid hikers might want more time on the trails. Check here for a good overview.
Read our full post here.

9. Explore the grounds and mansion at Naumkeag in Stockbridge. The summer home of attorney Joseph Choate, his wife Caroline, and their five children in the late 1800s, Naumkeag is the perfect representation of a country estate of the Gilded Age.  The original gardens included two terraces, a topiary garden, and an arborvitae alley. The Choate’s daughter, Mabel, inherited the property and spent significant time creating many additional gardens. She deeded it to the Trustees of the Conservation upon her death in 1958 and the 44 room estate was turned into a museum and opened to the public in 1960.
Kids will most enjoy running down the Linden Walk, dipping their hands in the garden pools, and exploring the mansion.
Travel Tips: Naumkeag is open daily from late May through early October. Due to current conditions for summer 2020, tickets are timed and must be reserved ahead of time- check here for more information; wear sneakers- many of the paths are stone or gravel and some staircases are steep; visitors check in at the Welcome Center, lower level of the mansion; the Gift Shop and Oak Cafe are also located on the basement level of the mansion. The Gift Shop features a wide variety of jewelry, housewares, gifts, and books about architecture and gardening; restrooms are located near the Welcome Center; plan on spending 30-60 minutes inside the mansion and another 60-90 minutes exploring the gardens.

Read our full post here.

10. Create your own culinary tour through the various towns and villages. There are literally HUNDREDS of dining options in the Berkshires- everything from quick service and coffee shops to formal, four course restaurants and resort dining and everything in between. There weren’t enough meals (or time) for us to test even a tenth of the spots, but we did have some great meals at the following locations:

1. Berkshire Mountain Bakery in Pittsfield- We went in for a pastry and ended up leaving with two very delicious thin crust pizzas.
2. The Marketplace in Pittsfield and Great Barrington- Great sandwiches, paninis, salads and breakfast dishes and omelettes. 
3. The Red Lion Inn in Stockbridge- also home to a 125 room hotel, the Red Lion Inn includes the Main Dining Room, Lion’s Den Pub, and the Widow Bingham’s Tavern. Both the Tavern and Pub are great for lunch and very family friendly. 
4. Alta in Lenox- Delicious entrees (pastas, steaks, and fish) and a good bar menu that pickier kids will like.
5. Brava in Lenox- Order ALL the tapas!! And then a few pizzas.
6. Haven Cafe in Lenox- One visit I devoured breakfast (eggs!bacon!toast!) and one visit I devoured homemade soup and salad- so many choices.
7. Shots Cafe in Lenox- Order all the pastries, AND muffins, AND croissants. We hear the coffee is pretty good too.
8. The Scoop in Lenox- For ice cream and sweet treats. Check online for hours- they are closed in the winter.
9. No. 6 Depot Cafe in West Stockbridge- My favorite avocado toast, muffins the kids will want multiples of, and plenty of outdoor seating. We stopped here all three times we visited the area this year.
10. For super special meals, I loved both Wheatleigh and Blantyre in Lenox, but have not taken the children to either spot. 

Looking for a family friendly place to stay while exploring the Berkshires? Check out our adventures at the Jiminy Peak Mountain Resort here.

For more of our City Guides, check out index here. And follow along on our adventures on Instagram, Facebook, Twitter, and Pinterest.

Disclosure: We were hosted by 1Berkshires for some of these activities. All opinions expressed are my own.