Want Decades of Fun Things to Do? Check Out the Berkshires in Massachusetts

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berkshires lake view
The Berkshires have it all. Photo credit: Judy Antell

The Berkshires has been a weekend getaway for my entire adult life. Right after graduating college, I returned to my native New York City, and college friends scattered along the East Coast. When we wanted to meet up with friends, we often gathered in a small town in the Berkshires in western Massachusetts, an easy drive from NYC. We loved seeing outdoor shows at Tanglewood and dancing at Jacob’s Pillow in summer.

When we had children, we would go to Hancock Shaker Village and the Norman Rockwell Museum, and on outdoor adventures like hiking or skiing at Jiminy Peak. I wouldn’t say it was an easy drive from New York City with three kids, but at least it wasn’t too far.

Those little kids became teenagers who looked at many New England schools, so we spent weekends on college campuses and exploring small towns and local Berkshires’ attractions like The Clark Art Institute and Mass MoCA.

Now, with my kids grown and gone, we have getaways with friends who own a house in Great Barrington. Outdoor activities include apple picking in fall and snowshoeing on the hiking trails in winter.

It’s rare to find a destination with enough appeal to be interesting for decades. The Berkshires is that kind of place and here are some of my favorite places and things to do.

Read More: 25+ Destinations to Take Your Teens Before They Leave for College

Bash Bish Falls waterfall & swimming area
The hiking trails at Bash Bish Falls State Park include waterfalls. Photo credit: Judy Antell

Outdoor Adventures: Hiking Trails in the Berkshires

We have enjoyed the hiking trails in the Berkshires year-round. You can see fall foliage in autumn, wildflowers in spring or summer and snowshoe in winter. And when there is no snow, a winter hike is almost as good.

Beartown State Forest in Great Barrington has over 12,000 acres of hiking trails. Bash Bish Falls State Park has the highest waterfalls in the Berkshires, plus great views. You can access the state park from New York or Massachusetts. You can even access the Appalachian Trail from Mount Greylock.

Appalachian Trail sign marker
Hiking trails through the Berkshires include a portion of the Appalachian Trail. Photo credit: Judy Antell

Mount Greylock

Mount Greylock, the highest peak in Massachusetts, offers panoramic views. If you’re not up to hiking all the way, you can drive to the top and access hiking trails form there. There is also mountain biking and cross country skiing.

Mount Greylock has a lodge for dining and overnights, not open in winter.

A snowboarder at Jiminy Peak
Snowboarding at Jiminy Peak Mountain Resort. Photo credit: Jiminy Peak Mountain Resort

Wintertime: Ski Resorts in the Berkshires

Advanced skiers and snowboarders may prefer the powder out west, but I’ll take Jiminy Peak Mountain Resort any day of the week. Three hours door to door from NYC, Jiminy Peak on the Taconic Mountain Range fits the bill for an easy ski trip with enough excitement for all. My husband and I could go snowshoeing while the kids skied and we have returned without kids for the hiking trails in summer.

The year round Jiminy Peak Mountain Resort has summer outdoor adventures too. There is mountain biking, a Mountain Adventure Park with ziplining, a Mountain Coaster and scenic chairlift rides; and an Aerial Adventure Park with self-guided, forest ropes course.

If you are just skiing or snowboarding for the day, Bousquet Mountain Ski Area in Pittsfield has a terrain park and plenty of downhill trails. There is day and night snow tubing. In summer, the ski trails become hiking trails. Bousquet hiking trails connect from Pittsfield to Lenox through a project of the Berkshire Natural Resources Council.

Other local ski areas: Butternut Ski Area in Great Barrington has 22 ski trails, two terrain parks and snow tubing. Berkshire East Mountain Resort in Charlemont has 38 trails, some open for night skiing and a snow tubing park. In summer. you can soar with the zip lines.

Read More: Top Ski Destinations in the New England

Summertime in The Berkshires

Jacob’s Pillow Dance Festival

The Jacob’s Pillow Dance Festival offers a nine-week season. The outdoor dance festival includes ballet, tap, hip hop and modern dance. There are also classes and workshops. Jacob’s Pillow is a National Historic Landmark.


Tanglewood, the summer home of the Boston Symphony Orchestra, is open year round, with free admission to explore the grounds. There are also guided tours. Note: Dogs are not allowed.

Summer is when you want to visit Tanglewood in Lenox. In addition to the Boston Symphony Orchestra, renowned musicians like James Taylor and the Boston Pops play here. Check their site for a full schedule of performances.

You can picnic on the lawn. And if you are on a family getaway, Tanglewood lets you bring up to four free children’s tickets per parent. [Sorry, Duggars, you have to buy more tickets].

Williamstown Theatre Festival

We have seen famous actors both onstage and in the audience at Williamstown Theatre Festival. Held on the campus of Williams College, this summer festival, with the unfortunate acronym WTF, brings theater, comedy and music to the Berkshires.

Bousquet Mountain Ski Area also has live music. You can picnic on the lawn, or buy food from the restaurant.

kayaks by lake
Take a boat out on the Housatonic River. Photo credit: Judy Antell

Get on the Water: Housatonic River

The Housatonic River starts near Pittsfield, flowing through western Massachusetts, into western Connecticut, and ending in the Long Island Sound. Hikers on the Appalachian Trail parallel the Housatonic River for a time.

If gentle canoeing isn’t exciting enough, Crab Apple Whitewater has whitewater rafting trips on the Deerfield River.

pumpkins in autumn at a farm
There is plenty to do regardless of the season in The Berkshires. Photo credit: Judy Antell

Year-Round Performing Arts in the Berkshires

Berkshire Theatre Group

The Berkshire Theatre Group has five stages in Stockbridge and Pittsfield. The Berkshire Theatre Festival, founded in 1928 in Stockbridge, and the Colonial Theatre, built in 1903 in Pittsfield, merged in 2010. The inclusive company includes “sensory-friendly” performances for people on the autism spectrum.

Barrington Stage Company

The Barrington Stage Company in Pittsfield is more than just a regional theater company. It premiered “The 25th Annual Putnam County Spelling Bee,” which moved to Broadway and won two Tony awards. Many of its new plays move to New York, so you can say you ‘saw it when.’

Clark museum exterior grounds
The Clark is a work of art, both indoors and out. Photo credit: The Clark Art Institute

Berkshires Museums

The Clark Art Institute

The Clark, in Williamstown has European and American paintings. When our kids were younger we would come with with our kids just for walking trails, and sneak in a little art. Then The Clark Art Institute expanded and added outdoor art. So even though you can come here in the rain, try to plan a visit on a nice day to enjoy The Clark indoors and out.

Mass MoCA

Massachusetts Museum of Contemporary Art, commonly known as Mass MoCA is the largest contemporary art museum in the U.S. The 19th-century mill buildings, a National Historic Landmark, began as a place for Williams College of Art to exhibit large works of contemporary art. Opening in 1991, Mass MoCA put the small town of North Adams on the map.

The Mount aerial view in wintertime
Winter at The Mount, Edith Wharton’s home. Photo credit: The Mount

The Mount

The Mount, a National Historic Landmark in Lenox, was author Edith Wharton’s estate and garden. The gardens and grounds are open for free, year round. The Main House, designed and built by Edith Wharton in 1902, is open from May through early fall.

A live outdoor concert series and an immersive sound and light experience in early winter are some of the programs the venue puts on.

Norman Rockwell Museum

Norman Rockwell Museum in Stockbridge is a showcase for Norman Rockwell’s art, but it also has other American illustrative art.

Though the Norman Rockwell Museum is open year-round, Rockwell’s Studio and the Café are not open in winter.

The Berkshire Museum

The Berkshire Museum in Pittsfield has an aquarium, natural history exhibits and The Feigenbaum Hall of Innovation. You can cultivate your kids’ STEM interest or just learn about some really cool stuff at The Berkshire Museum.

Destination Spa: Lenox

Canyon Ranch in Lenox has been on my bucket list for a long time. This luxury retreat has spa services, outdoor activities like hiking, tennis and pickleball and year round indoor yoga, cooking classes and strength classes in a pool. And there is the spa. If you’d rather not commit to an overnight stay, Canyon Ranch offers day passes.

Read More: Wellness with a French Accent: Le Monastere des Augustines in Quebec

There is plenty of fine dining in Lenox. Photo credit: Judy Antell

Dining in Lenox

Since Lenox has so many cultural institutions, it supports a thriving restaurant scene. Our favorite place, Frankie’s Ristorante Italiano, has an entire vegan menu as well as meat for the carnivores, making it a crowd pleaser.

dog at distillery
Bring your furry family members along to Berkshire Mountain Distillers. Photo credit: Judy Antell

Berkshire Mountain Distillers

Berkshire Mountain Distillers in Sheffield offers free tastings of its gins, vodkas and bourbons. Live music attracts empty nesters with dogs, families and vacationers seeking out locally made spirits. A collaboration to support local cultural institutions includes craft cocktails like the Edith Wharton, made with rye, amaro and vermouth.

stone barn at HSV
The Round Stone Barn at Hancock Shaker Village. Photo credit: Hancock Shaker Village

Hancock Shaker Village

Hancock Shaker Village, a living history museum in Pittsfield, has one of the oldest working farms in the Berkshires. There are 20 historic Shaker buildings, including The Round Stone Barn.

Though Hancock Shaker Village is a great family destination, my husband and I first visited here without children. There is plenty to see and do, including the hiking trails, which link up to Pittsfield State Forest.

That being said, Hancock Shaker Village lives on in our family lore. We were watching a kitchen demonstration, where one of the costumed interpreters was making cookies. Of course, you get a cookie and and my youngest daughter was eagerly awaiting one when I asked what shortening was used. The answer, lard, meant none of us were taking a cookie. There were tears, but there was also ice cream at the café. Crisis averted.

The estate and gardens at Naumkeag
The estate and gardens at Naumkeag. Photo credit: The Trustees


The Naumkeag estate includes a 19th century 44-room “cottage” and eight acres of formal gardens. It’s a National Historic Landmark in Stockbridge and is only open seasonally. There are special events in the fall, winter and spring, but if you want to see the house, come in summer.

Note: Naumkeag is not ADA compliant and is not stroller accessible.

Pleasant Valley Wildlife Sanctuary

Pleasant Valley Wildlife Sanctuary in Lenox has walking trails where you can see from Mount Greylock to the Taconic Range. As you hike through the forests, meadows and wetlands, look for the resident beavers and other wildlife.

Berkshire Botanical Garden

The Berkshire Botanical Garden in Stockbridge, specializes in plants grown in the Berkshires. Indoor exhibits are open year-round; the botanic gardens are open May through October. Don’t miss the topiary garden and the Daylily Walk. Free guided tours are included with admission.

Hilltop Orchards

If you think apple picking is just for families, Hilltop Orchards will set the record straight. Hilltop Orchards has a 100 year orchard and you can pick your own. But there are also craft ciders (not kid-friendly), a winery and apple cider donuts.

Hilltop Orchards is in Richmond, just over the New York border, so it makes a great day trip from NYC. You can go hiking, cross country skiing or snowshoeing here, too.

Judy Antell is an empty-nester mother of 3 who spends a lot of time visiting her daughters. Why don’t they live in Brooklyn? Judy and her husband love to travel, by bike, car, or plane, whether to see their kids or have friend or couple adventures, mostly centered around vegetarian food.
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2 responses

  1. I haven’t seen anything about Springfield – ever. As the birthplace of basketball and having a Hall of Fame and the gun museum I would think it deserves some mention .

    1. There is also a wonderful Dr. Seuss museum. But I don’t think Springfield is part of the Berkshires

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