Dream Time In The Berkshires

Over a nightcap in the bar, she revealed that their 12-year daughter Chloe had come out both gay and genderless earlier this year. “They first told us, then in a videotaped poetry slam for their school project,” informed Charbonneau, using the gender-neutral pronouns Chloe prefers. “That’s been a challenge,” she says, “but so far, this has been a positive move for them.”

During the hour-long car ride back to Tom Kaegi’s house, transported by our misty mountain hop, I thought of one wisdom Mamma Frasca shared with Dylan that day back in 1975: “With love you’re like the egg. Without love, you’re like the hollow egg, without yolk, all white.”

The Berkshires are the whole egg and more, hatchery for all manner of inspiration, poetry, and otherworldly dreams.

In 1844, naturalist, philosopher and Walden author Henry David Thoreau “sauntered” to the summit of the Berkshires’ 3,491-foot Mount Greylock, the state’s tallest peak. Overnighting there in a lean-to, he recounted his sunrise awakening in A Week on the Concord and Merrimack Rivers (1849), calling Greylock “a dweller in the dazzling halls of Aurora” and the surrounding panorama “…such a country as we might see in dreams, with all the delights of paradise.”

Car-accessible from mid-May to early November, and year-round via paths including the Thunderbolt Trail and Appalachian Trail (which passes through the Berkshires from top to bottom), the mountain’s crowning 93-foot tall WWI War Memorial (slated to reopen in 2016), offers five-state, 90-mile panoramas from its observation deck.

Also at the summit is the rustic Bascom Lodge. Built by the Civilian Conservation Corps for hikers and nature enthusiasts, this 76-year old Arts & Crafts-style stone and timber-frame heirloom hosts seasonal dining and overnight stays in a mix of private rooms and bunks.

Another historic figure stirred to lofty praise by the region was the Reverend Henry Ward Beecher. Around 1853, the famed preacher and abolitionist acquired a hilltop near Lenox and reportedly declared, “From here I can see the very hills of Heaven.” Since 1880, that same spot has been home to one of the Berkshires’ premier properties, the family-friendly Cranwell Resort, Spa & Golf Club.

Inspiring moments abound across the generally liberal, accepting, and equality-minded Berkshires for families, elevating the four-season destination to the preeminent travel category of escape.

Under three hours by car from New York City and Boston, the region, defined as “The Berkshires of Western Massachusetts” or simply “The Berkshires,” includes some 32 towns, villages, and communities within the official state boundaries of Berkshire County. However, locals say The Berkshires—also describing the Appalachian Mountain range running through here from neighboring Connecticut—is a “state of mind” extending into western New York, northwestern Connecticut, and southern Vermont.

Tracing a scenic 18th century settlement path, key visitor coordinates along north-south Route 7 include newly hip foodie draw Great Barrington (incorporated 1761); Lenox (1767), once the “Inland Newport” for its magnificent Newport-like “Berkshire Cottages”; artful Stockbridge (1739); the county seat of Pittsfield (1761); liberal arts bastion Williamstown (1765); and former mill town North Adams (1878).

Pick a category, and the Berkshires are ready to engage. The great outdoors lead the way, with the annual fall leaf show here among the world’s best.


Along with Greylock, another prime aerie for enjoying the autumnal blaze is Great Barrington’s all-season Monument Mountain. One of 120 Massachusetts nature and historic sites managed by the Trustees of Reservations, Monument Mountain features three trails, each under three miles. Follow in the footsteps of Native Americans and literary greats Herman Melville, Nathaniel Hawthorne, and Oliver Wendell Holmes (who picnicked here together in 1850) up 1,642-foot Squaw Peak, with distant Greylock and New York’s Catskill Mountains visible on clear days.

Another choice Trustees’ property is Bartholomew’s Cobble in historic Sheffield (1733), the Berkshires’ first incorporated town. Named a National Historic Landmark for its remarkable geology and bio-diversity, this fern heaven features five miles of trails, including the hike to 1,000-foot Hurlburt’s Hill, plus caves, beaver ponds, and access to the historic Ashley House. Part of the Berkshire 18th Century Trail, this 1735 structure is where Mum Bett sued for freedom and helped end slavery in Massachusetts.

Also on the trail is Arrowhead, Herman Melville’s Pittsfield home from 1850 to 1862. So named by Melville for artifacts he found buried on the property, the national landmark farmhouse offers guided house tours, ending in the study where, inspired by distant Mount Greylock, Melville wrote his whaling classic Moby Dick.

With three winter-only and three all-season resorts, the Berkshires are a wonderland for outdoor adventure. The former set includes historic Catamount in South Egremont; Great Barrington’s Ski Butternut; and the smaller Otis Ridge in Otis. Open year-round are Bousquet in Pittsfield, mighty Jiminy Peak in Hancock, and Berkshire East in Charlemont. All feature ziplining and adventure courses, with a popular alpine slide at Jiminy.

Opened last summer, Ramblewild (see Adventure Time sidebar) redefines the tree-to-tree aerial experience. Located along the Mohawk Trail (Route 2) and Deerfield River in the eastern Berkshires, Zoar Outdoor offers a suite of family-friendly programs. With lodging and camping facilities available, adventures go from gentle tubing to full-on whitewater rafting, plus classes in kayaking, rock climbing and more.

The Berkshires’ heritage and cultural assets rival major cosmopolitan centers. Continue east on Route 2 to discover national landmark Historic Deerfield, featuring original 18th and 19th century structures along a mile-long street from 1671; the 24-room Deerfield Inn; and Flynt Center of Early New England Life. The “Deerfield Lunch Box” food truck, created after Hurricane Irene, is a great casual option.

Wind back on the Mohawk (mind the hairpin turn in winter) into North Adams, where the triumphant Massachusetts Museum of Contemporary Art, or Mass MoCA, is the nation’s largest center for contemporary visual and performing arts.

As chronicled in the 2000 book From Mill to Museum, this original Colonial-era manufacturing site served as the Arnold Print Works (1860–1942) and then the Sprague Electric Company (1942-1985), renowned for high-tech contributions to WWII, the atomic bomb and Gemini moon missions. In 1999, it reopened as Mass MoCA, providing a catalyst for still revitalizing North Adams.

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