All-Season Family Fun and Activities Abound: A Road Trip to the Berkshires

For our family, a great road trip usually involves some place where we can establish a home base and take a variety of quick trips from there. It’s like having little mini-adventures within the overall trip. It also allows us to play things by ear, depending on the weather or whether our daughter is up for certain activities. During a recent weekend trip to the Berkshires in Western Massachusetts, we found we had plenty of options.

Home to quintessential New England towns like Stockbridge, Lenox, and Williamstown, the Berkshires offer a wide mix of outdoor adventures like hiking and skiing; cultural venues, like MASS MoCA and Tanglewood Music Center; and some great dining and lodging options.   

Rainy (or Cold) Day Activities in the Berkshires

One of our planned activities during the weekend was skiing at Jiminy Peak Mountain Resort in the town of Hancock. And while I was able to get in a few great runs one morning, with brutally low windchill temperatures, we focused on some indoor activities.

A Slice of History: Exploring Gilded-Age Properties 

The Berkshires are home to numerous Gilded-age mansions that make for great exploring, the most famous of which is The Mount, home of writer Edith Wharton. Located in Lenox, The Mount is a museum and cultural center, where visitors can tour the house and immaculately manicured grounds featuring beautiful gardens and terraces (on nice days). Kids can keep an eye out for the stuffed dogs found throughout the house, a testimony to the writer’s love of dogs. 

While the grounds are open throughout the year, the house closes down for the winter season, so we headed to another historic property in Lenox: Ventfort Hall. We got a fascinating guided tour, learning about the history of the property, built by financier JP Morgan’s sister as a summer house in 1891, as well as the ongoing restoration efforts. Our daughter was fascinated by little details, like the mounted exotic butterfly displays, and hearing some of the ghostly legends. 

Visitors can also check out their calendar for special events, like marionette shows and ghost tours.  

Art Appreciation at the MASS MoCA

Another great indoor activity is the Massachusetts Museum of Contemporary Art, or MASS MoCA, in North Adams. Visiting an art museum may not be most kids’ idea of a fun time, but MASS MoCA isn’t your typical art museum. It’s set in a rehabilitated mill building, a reminder of the town’s past as an important textile producer. The expansive rooms in the buildings allow for massive art installations that take advantage of the space and acoustics.

As we wandered throughout the museum, crossing through tunnel-like bridges that connect the various buildings, it felt like we never knew what was going to be around the corner — a darkened room showing videos and pumping out loud dance music, a bright open room with thousands of of lightbulbs shining like stars of a galaxy, or a simple space with a MC Escher-esque shape projected on the wall. 

Of course our daughter’s favorite part was Kidspace. This dedicated kid-friendly area had numerous work stations and art projects to choose from, complete with helpful staff on hand to guide us.

As an added bonus, the MASS MoCA campus is also home to several restaurants and a family (and dog) friendly taproom, Bright Ideas Brewing. Enjoying a cold beer with some food from the neighboring cheesesteak spot was a great way to end our visit. The museum also hosts an impressive array of artists and well-known musicians for shows; those planning to head to the museum should be sure to check out the line-up of upcoming events.  

Reading and Relaxation at Lenox Library

Ever since I was young, I’ve loved going to libraries. As an adult, I’ve come to appreciate them even more. There’s something so appealing about the idea of a place where, even as a visitor to the town, you can pop in and know there will be a quiet spot to relax with a book, learn about local history, or find some kid-friendly activities.

We spent a morning in the Lenox Library, which is housed in a beautiful 1800s-era brick building adorned with massive white pillars. The inside features an open reading area with comfy chairs and a great children’s room. Our daughter felt right at home here, quickly settling in the toy kitchen with some of her favorite books.  

Dining

There’s no shortage of great dining options in the Berkshires. We found two favorite spots, both of which we’d go back to in a heartbeat. For breakfast, we went to the Patisserie Lenox, a classic French bakery and cafe with truly delicious pastries, breakfast staples, and lunch faire. Both their breakfast and lunch sandwiches are made that much better by the flaky croissants on which they’re served. 

Our other favorite was the Blueberry Hill Market Cafe just over the state line in New Lebanon, New York, where we had a delicious dinner, and the complimentary mini blueberry and cornbread muffins were a big hit with our daughter. Originally operating as a breakfast and lunch cafe, they’ve expanded to offer a dinner menu. They’re also home to a market, bakery, and bar.

Judging by the servers’ interactions with other diners, this place is obviously popular with locals, and for good reason. 

Accommodations

Our home for the weekend was a tiny home at Huttopia Berkshires, which features seasonal wood and canvas tents along with a dozen year-round tiny houses. They all came with fantastic mountain views, including the slopes of Jiminy Peak. This was our first tiny house experience as a family, one we would definitely repeat. 

We loved the cabin design, where the space is maximized for living area and storage. In the winter months, the cabin features three heat sources to keep it nice and cozy (a wood stove, mini-splits, and electric heaters in the bedrooms). For warmer weather, there’s a nice front porch and large screen door. The property includes hiking and mountain biking trails, and guests can take advantage of the pool, communal fire pits, and playground in the warmer months. 

While the entire house wasn’t much bigger than a standard hotel room, the fact that it’s divided up into the living room/kitchen area and two bedrooms (one with three bunks) meant that we could stay up for a while after our daughter went to bed.

Packing Must-Have’s for a Tiny House Vacation

• Coffee and some ingredients for an easy meal: The full kitchen was great for saving a little money and preparing some meals at home. 
• Boardgames, construction sets, and cards: The central table with an L-shaped booth was perfect for games.  
• Slippers/indoor shoes: A change of footwear came in handy when to keep the floors free of dirt and snow.  

Other Lodging Options in the Berkshires

While we loved our tiny house experience, the somewhat rustic experience may not be for everyone. Luckily there’s no shortage of lodging openings, including numerous short-term rentals. For those looking to stay close to MASS MoCA, The Porches Inn at MASS MoCA features rooms set in seven renovated mill buildings, with a sauna, outdoor hot tub, and four-season outdoor pool. 

The adventurous type might consider making the Country Inn at Jiminy Peak their home base. The Inn features an array of privately-owned condos for rent, and guests have access to hotel amenities like tennis and pickleball courts and the outdoor heated pool. In the winter, guests have prime access to Jiminy Peak’s ski slopes. Summertime visitors can check out the Mountain Adventure Park to ride the mountain coaster and alpine slide, among other attractions.  

Destination: Berkshires

We had no problem filling up the days with activities during our three-day stay and felt we had barely scratched the surface of things to do in the area; we could’ve easily extended the trip another few days. Just two hours from Boston, an hour from Hartford, Connecticut, and 45 minutes to Albany, the Berkshires are easily accessible for everything from a day trip to an extended vacation.

And while we loved the quiet vibe and snow-blanketed scenes of winter, we’ll definitely be back to take advantage of all the warm weather activities.  

Photos by Bart Beeson

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About the Author: Bart Beeson is a New Hampshire-based freelance writer focusing on travel and outdoor activities. He has been published in The Washington Post, Business Insider, USA Today, Travel Weekly and other media outlets. When he’s not traveling, he can be found hiking in the White Mountains with his dog Kesey. See more of his work at bartbeesontravel.com.

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