Trails Less Traveled
An outlier’s guide to hiking, biking, and paddling
The most important thing is to enjoy, says Odin Adolphson, here leading a hike at Basin Pond in Lee. “There is just so much hidden away and untapped.”
Photos Megan Haley
Odin Adolphson has come to know the Berkshires via a rather circuitous route. His arrival in the States in 1992, to attend Worcester’s Clark University, came by way of Kenya (where he was born); Madras, India; Tehran, Iran; and Singapore before he experienced what he calls the biggest culture shock of his life—settling in western Massachusetts.
For this avid outdoorsman, who credits his parents with instilling in him a sense of adventure, Adolphson made quick work of getting off the beaten track and exploring what the Berkshires had to offer. His introduction to local outdoor adventure came by way of a job at the Arcadian Shop in Lenox, where he was often called on to lead an impromptu paddling excursion on Stockbridge Bowl or hike in nearby Kennedy Park. Ultimately, this gave way to starting his own outfit, Happy Trails Guiding in 2008. He has spent the past decade discovering a multitude of hidden natural gems nestled throughout the Berkshires.
“I love guiding, and I love being out in the woods,” says Adolphson who, on a recent weekday morning, introduced me and my two daughters to Basin Pond in Lee. We found our time on the trail under Adolphson’s tutelage to be a multifaceted adventure. The lollipop trail, so named for the quick hike in on the “stick” before veering left or right in order to complete the loop, is easily accessible from Becket Road (off Route 8) in Lee. Thanks to nearly seven inches of rain in the two weeks prior to our excursion, the woods were mossy, wet, and wonderful. We spied red efts darting across leaf-strewn paths and noticed mushrooms ranging in hues of crimson and vermilion to purple. Clumps of ferns unfurled in the shade near the trailhead before giving way first to a coniferous forest of mostly hemlock and then to a deciduous forest teeming with beech.
“We are extremely lucky to have the Berkshire Natural Resource Council as stewards of the land out here,” Adolphson says, pointing to hash marks on select stones made by a grinding wheel in order to facilitate crossing of the numerous streams feeding the natural catch basin. We even encountered a talus slope—a geological feature resulting from crumbling stone promontories left over in the wake of glacial activity—recognizable by boulders of various sizes along the trail.
At Happy Trails Guiding, Adolphson’s knowledge is augmented by six part-time guides and a fleet of gear that includes 48 hybrid bikes and 24 kayaks. He and his staff, all of whom share a love of the outdoors and have personalities to match, can accommodate groups ranging in size from a single family to wedding parties and camp groups. Adolphson works closely with Berkshire Outfitters in Adams, Berkshire Bike and Board in Great Barrington and Pittsfield, and the Arcadian Shop—for referrals and for sourcing equipment and supplies.
Here are some of Adolphson’s top picks for trailblazing and exploring the Berkshires this fall, with or without a guide.
Hiking: On days when the parking lots at Monument Mountain and Mount Greylock suggest the trails will be crowded, Adolphson favors a section of the Appalachian Trail in Monterey, just west of Ski Butternut off Route 23. Hiking north through a series of steep climbs, the reward is a series of granite ledges that offer dramatic, rolling views. This is an in-and-out hike rather than a loop trail. Farther south, in Sheffield, Race Brook Falls presents a more challenging incline. Accessible by Route 41, just north of the Connecticut line, this hike boasts cascading streams, thick pine forest, and beautiful waterfalls.
Biking: “Mountain biking is my wheelhouse,” says Adolphson, who estimates he spends 80 percent of his free time on a bike in the woods. October Mountain State Forest in Lee offers 40 miles of “single track,” specifically designed for mountain bikers and a fun way to explore new terrain. Beartown State Forest in Monterey has a beautiful 11-mile loop that skirts Benedict Pond and is a popular place to encounter Appalachian Trail thru-hikers. Pittsfield State Forest offers an amazing network of mountain-bike trails as does Lenox Mountain, beginning in Kennedy Park.
Paddling: “One of the gems of the Berkshires is the Housatonic River,” says Adolphson who, when it comes to paddle sports, typically avoids big lakes and their boat traffic. He recommends a section in Lenox, stretching from the Sportsmen’s Club on New Lenox Road and ending at Woods Pond in Lenox Dale, as a favorite. Despite the short route, a scant half-mile as the crow flies, this excursion takes roughly 2-1/2 hours, thanks to a quick succession of oxbows, or nearly 90-degree bends in the river, and offers various wildlife, including blue herons, muskrat, and lots of ducks. Surprisingly, the two trailheads are just a ten-minute drive apart. Adolphson also likes the outlet at the south end of Stockbridge Bowl as well as Buckley Dunton Lake in Becket— magical in late summer and early fall when wild blueberry bushes line the shore.
In the Berkshire wild––Civilization and help are never far away, Adolphson says. But be prepared: water, a jacket, the basics. Always opt for sturdy shoes rather than flip-flops for unexpected quick exits.