Family Fun with the Trustees of Reservations: First Stop, the Berkshires


One of our specialties at ActiveTravels is designing the Dream Day Itinerary for trips around the globe. With the independent traveler in mind, we create what we consider a perfect day of travel, including recreational activities, cultural or historical sites, recommended restaurants, and lodging. This week, we’re delighted to partner with the nonprofit conservation organization, The Trustees of Reservations, to link together a sampling of their 113 sites in Massachusetts. We’re going to break down 5 regions in the state and focus on family travel, including as many special summer events as possible. 

Today, we’re going to focus on the Berkshires. Heading south to north, start your day with a leisurely stroll along the Housatonic River at Bartholemew’s Cobble. Walk on the Ledges Trail and you’ll find the river snaking through dairy farms. The Trustees take full advantage of the Housatonic, offering guided canoe trips on designated Saturdays and Sundays in the summer. You’ll learn about the history of the area and be on the lookout for bald eagles flying overhead. If you love birds of prey, join wildlife rehabilitator Tom Ricardi this coming Saturday, June 27, from 10 am to noon, to view the hawks, owls, falcons, eagle and turkey vulture that he cares for. On Saturday, July 18th, from 10 am to noon, you can scour the forest and field for snakes, frogs and salamanders with a naturalist guide. Over Labor Day, sign up for the family campout at Bart’s Cobble and you’ll be treated to guided hikes, scavenger hunts, a search for owls, and, of course s’mores around the campfire. Also note that if you sign up for a Family Explorer Membership at Bart’s Cobble and 4 other Trustees sites (Crane Beach, Naumkeag, World’s End, and Long Point on Martha’s Vineyard), kids will receive an Elliott the Hermit Crab stuffed animal, a Get Out and Explore Booklet featuring 12 quests or scavenger hunts, cool tattoos, and more. 

A shot walk from Bart’s Cobble and you’ll find the circa-1735 Ashley House, the oldest house still standing in Berkshire County. Colonel Ashley was a judge and patriot who supplied iron and other supplies for the Revolutionary War effort. On tours on weekend days in summer, you’ll hear the story of Elizabeth Freeman, a slave of the Ashleys who sued her way to freedom. On Saturday, August 22nd, from 1-4:30 pm, come celebrate Elizabeth Freeman’s life with performances, an art exhibit, plus house tours. 

Heading north, stop at the trailhead to Monument Mountain on Route 7. No family trip to the Berkshires is complete without a 45-minute trek to the top of this 1,642-foot peak. The gradual climb on a path through hemlocks, oaks, beech, white pines, red maples, and birches leaves you at the top with vistas of Mt. Everett to the south and New York’s Taconic Range to the west. While hiking, tell the kids this is where the writer of Moby Dick, Herman Melville, first met the author of The House of Seven Gables, Nathaniel Hawthorne. The date of their hike was August 5, 1850.

A 15-minute drive from the base of Monument Mountain and you’ll reach one of the gems on the Trustees roster, Naumkeag. This 44-room Berkshires “Cottage” from the Gilded Age was designed by the renowned architectural firm of McKim, Mead, and White. But it’s the gardens that you’ll want to roam, a landscaping marvel thanks to 28 years of collaborative work by former owner, Mabel Choate, and her dear friend, Fletcher Steele, one of America’s first modern landscape architects. Naumkeag is in the fourth and final phase of a $3.3 million renovation, currently mending the retaining wall and fixing the fountains of the elaborate Chinese Garden. In the meantime, walk the iconic Blue Steps, lined with newly planted birches. Then savor the gardens while dining on a picnic lunch brought to you by the Red Lion Inn’s Oak Café. 

Thursdays in summer at Naumkeag, from 11 am to 4 pm, feature lawn games in the gardens. Games include croquet, badminton, bocce and jumbo versions of classic tabletop games such as Checkers, Jenga and Connect Four. Also on Thursday, from 2 pm to 2:45 pm, is a house tour designed for children. Or head to Naumkeag for Watermelon Wednesdays, four Wednesdays in late July and August, from 4:30 pm to 6 pm, where you not only get to chomp into fresh watermelon, but watch live theater, music, and storytelling. On July 3rd, there will be a special Free Fun Friday at Naumkeag, where families can watch performances by BerkCirque and singer/storyteller John Porcino; create art, enjoy the lawn games, and take kid-friendly tours of the mansion.   

End your day in the Berkshires at the Williamstown property Yankee Magazine recently dubbed “Best Retro Lodging” in New England, The Guest House at Field Farm. Enter the Bauhaus-era home, now a 6-bedroom inn welcome to children 12 years of age and older, and you feel you just entered the set of Mad Men, season one. Views on the back porch overlook mighty Mount Greylock, the state’s tallest peak. The inn is set on 316 acres, perfect for viewing the night sky after a day of adventure.