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Four spots where nature meets history in western Mass.

View from Pocumtuck Ridge in Deerfield

The view from the Pocumtuck Ridge in Deerfield.

Western Massachusetts in the summertime is known for concerts at Tanglewood, dance performances at Jacob's Pillow, and contemporary art exhibits at Mass MoCA. Literary buffs vacationing here can visit Emily Dickinson's home in Amherst, Edith Wharton's estate and gardens at The Mount in Lenox, and Herman Melville's Arrowhead in Pittsfield.

But there are also plenty of opportunities for enjoying the outdoors. You can hike the Berkshire Mountains, find connections to local history, or just spend a pleasant afternoon in the woods.

Here are four spots worth exploring: Questing, Pocumtuck Ridge, High Ledges and Mount Tom.


 This 438-acre swath of cloistered forest, open meadow, ancient stone walls and crumbling cellar holes is called Questing, named for a snake-headed monster from the legends of King Arthur.

The area sprang to life as a farming settlement in the 1700s. "But when the Midwest opened up, the area was gradually depopulated," said Will Garrison, the cultural resources manager for The Trustees of Reservations, the land preservation organization that now owns Questing.

The land was completely abandoned by the 1930s and was purchased in the 1940s by Robert and Jane Lehman, who bestowed the Arthurian title and later bequeathed it to The Trustees. The Lehmans allowed the former farmland to grow wild, but the fragments of the area's former civilization are impossible to miss. Walking past the cellar holes and stone walls, it's easy to imagine property borders, boundaries for cattle and plots of tobacco, potatoes and grains.

A short, easy trail leading to the ruins narrows in places, plunging steps into an overgrown carpet of soft ferns. The area still conjures a mythical feeling as thick, sinewy vines twist around maples and oaks, choking their way into the treetops.

"The place is in the middle of nowhere," said Alex Olchowski, an artist from nearby Lee who says he's run into only a handful of people in the hundreds of times he's been to Questing. "But you get the sense that people were living their lives there at one time."

The property is accessible from New Marlborough Hill Road, New Marlborough. Allow 90 minutes to walk the trails. Details at thetrustees.org/place/questing.


It's a quick getaway for mountain bikers and hikers hoping for some fast scenic payoffs. But Pocumtuck Ridge is also a vantage point for the Connecticut River Valley's geological history and mythic lore.

The 200 million-year-old ridge between Deerfield and Greenfield now overlooks bucolic farms and homes tucked safely in the valley below. But it was once witness to violent changes in the landscape. When glaciers helped carve out the valley, the rock in the ridge was so durable that it resisted erosion. As the water drained away, the ridge was left as a towering overlook, part of a topography that helped establish the Pocumtuck Indian myth of a giant beaver that once terrorized the area.

According to the legend, the waterlogged valley was home to a beaver who gave its hungry attention to the humans living in the area. Turning to the spirits for protection, the Pocumtucks are said to have summoned a giant hunter who slew the beaver, causing it to sink to the bottom of the lake and turn to stone. From a bird's eye view, its head and shoulders seem to have formed the Sugarloaf mountains, while its body and tail stretch the length of the Pocumtuck Ridge.

Most of the hiking and mountain biking done on the ridge is now contained to a roughly three-mile stretch between northern Deerfield and North Sugarloaf Mountain, where a well-marked path offers a changing terrain through hardwood and evergreen trees.

"It gives you just about every kind of riding environment you can find," said Bob Perry, the former owner of the now-closed Bicycles Unlimited in Greenfield, who lead frequent mountain biking expeditions along the ridge. "You've got fast terrain, steep climbs and steep downhills. It's just about the nicest single track through a forest that you can find."

A service road and a woodland trail leading to the ridge can be accessed on Pine Nook Road in Deerfield. Blue blazes mark the Pocumtuck Ridge Trail.


Sunlight seems scarce in the thick woods near the High Ledges, where trails wind past twisted roots, gnarled branches hang overhead and strange beauty pokes through the damp forest floor. Low-lying ferns and clusters of mountain laurel line the paths that dip toward boggy areas and climb to rocky heights, all under the canopy of towering evergreens, sugar maples and oaks.

Wolve's Den Trail leads to patches of sundews and pitcher plants that swallow bugs in a gentian swamp. The sanctuary is studded with pink and yellow lady slippers in the early summer, and different types of orchids come to life throughout the year. Black snake root, horse balm and liver leaf have all found a place to grow among wild ginger and yellow violets.

"It's one of our best botanical sanctuaries," said West Region Property Director for Mass Audubon, Ron Wolanin.

"We love coming out to western Massachusetts, and this seems like the most pristine of all the trails we've been on," said Teresa Peacock of Brooklyn, N.Y., who visited High Ledges in 2006 with her husband and three children.

After looping along the secluded paths, the High Ledges offer a panoramic view of the valley. Mount Greylock, the state's highest mountain, is visible from the rock outcroppings that look over native red pines. The village of Shelburne Falls, the Deerfield River and the Mohawk Trail quickly come into view, but a quick retreat shrouds visitors once again in the sanctuary.

The site is located off Patten Road in Shelburne. Details at massaudubon.org/get-outdoors/wildlife-sanctuaries/high-ledges.


From a distance, it's easy to dismiss Mount Tom as an unimpressive hump lurking over Interstate 91. But pull into the Route 5 entrance of the Mount Tom State Reservation, which straddles Holyoke and Easthampton and you enter a 2,000-acre forest with a 22-mile network of trails past trickling streams, through towering trees, leading to some of the most expansive vistas in western Massachusetts.

A relatively easy climb up the T. Bagg Trail hooks up with the Metacomet-Monadnock, the long-distance trail that stretches from Connecticut to New Hampshire. Its span within the Mount Tom Reservation leads to Goat Peak at 800 feet, where a clearing looks down the mountain's west side over Easthampton. To the south, Mount Tom's soft, rounded 1,115-foot summit towers over the valley, striking a more majestic pose than it does from the highway below.

For an even better view from Goat Peak, it's worth a climb up the nearby tower that was built for viewing the annual autumn migration of hawks. From Goat Peak heading south, the M-M trail pitches downward, popping out at a road that cuts through the park from Holyoke to Easthampton. Follow the road for a few yards, then take the trail back into the woods, where a flat pathway soon slopes into a steep climb.

A series of cliffs are easily accessible, with different views at each outcropping.

The M-M trail leads out to Mount Tom's true summit, where you'll find some antennae but no spectacular views. From the cliffs overlooking Easthampton, a series of trails lead off the mountain, looping back toward a parking area not far from the T. Bagg trailhead.

Details at mass.gov/locations/mount-tom-state-reservation.

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