Hit the Trails !
A curated guide to some of the best hiking trails
Trails with Waterfalls
Mount Greylock State Reservation — March Cataract Falls Williamstown and New Ashford Department of Conservation & Recreation To reach the trailhead that leads to March Cataract Falls , park in the Mount Greylock State Reservation parking area on Rockwell Road in Williamstown , then follow Rockwell Road and Sperry Road to the trailhead access point . The hike to March Cataract Falls is a 2.2-mile “ out and back ” hike , which leads to a small and picturesque waterfall . The trail is a good fit for hikers of moderate ability .
If you are interested in further waterfall sightseeing at Mount Greylock State Reservation , you ’ re in luck ! According to Odin Adolphson , owner and founder of Berkshire-based Happy Trails Guiding , LLC , Mount Greylock State Reservation is one of the crown jewels of our state lands — and it also is home to seven stunning waterfalls , five of which are officially listed . “ If you talk to most hikers in the Berkshires , most of them will say that they ’ ve only been to two of the waterfalls that are on the main trail ,” notes Adolphson . He adds that the waterfalls are all listed on the maps at the Information Center at the base . “ If you want to visit all of the waterfalls , you can make a fun trip out of it and really explore the land in the process ,” he says . Many trails at Mount Greylock State Reservation also are open to mountain bikers , including the popular Bellows Pipe Trail and the Glen Meadow Loop , among others .
Windsor Jambs Windsor Department of Conservation & Recreation The Windsor Jambs Brook Trail is another one of Adolphson ’ s favorite waterfall trails . This 2.1-mile loop trail is accessible from the trailhead off of Schoolhouse Road . The beginning of this relatively easy , family-friendly hike follows the Windsor Jambs Brook and offers wonderful waterfall views . After finishing
72 // BERKSHIRE MAGAZINE Fall 2022
By Benjamin Lerner
Photos by Odin Adolphson
Boasting gorgeous mountain vistas , pristine woodlands , and verdant meadows , the Berkshires is home to some of the best hiking trails . Whether you ’ re looking to take in the breathtaking sight of a majestic waterfall , challenge yourself across a rugged route over a mountain , explore a celebrated backwoods ski trail , or enjoy a family-friendly and accessible stroll through the wilderness , hikers of all skill levels will find ample opportunities to immerse themselves in nature ’ s boundless beauty . We have worked with passionate members of our hiking community to create a guide , so lace up your hiking shoes , fill up your water bottles , and get ready to hit the trails !
the hike , Adolphson recommends stopping by the Sangar General Store at the intersection of routes 9 and 8A for a tasty snack . “ They ’ ve got the best samosas ,” he says . “ Don ’ t forget to get the chutney side .”
Race Brook Falls Sheffield Department of Conservation & Recreation Hikers of moderate ability will no doubt savor an excursion to Race Brook Falls in Sheffield . The trailhead for this 3.6-mile “ out and back ” hike is located on Route 41 / South Undermountain Road . Although the terrain is steep , rocky and bumpy , the views from the top are unforgettable . The trail is fairly popular , so expect to see other travelers along the way . It is best when visited from March through November .
Stevens Glen West Stockbridge Berkshire Natural Resources Council For a short , moderately difficult hike with fabulous waterfall views , look no further than Stevens Glen in West Stockbridge . The trailhead is accessible from Lenox Road and leads to a one-mile loop trail with an observation deck that overlooks Lenox Mountain Brook . While traveling along the trail , hikers will walk through dense glades that open up to a romantic waterfall in a steep ravine . The trail is fairly popular , so expect to see other hikers while making your way towards the waterfall . Stevens Glen is open year-round and is an ideal destination for snowshoeing .
Old Ski Trails
Thunderbolt Ski Trail / Bellows Pipe Trail at Mount Greylock State Reservation Adams Department of Conservation & Recreation Located on the eastern face of Mount Greylock , the Thunderbolt Ski Trail was built by the Civilian Conservation Corps ( CCC ) in 1934 . The trail once hosted many high-profile ski events , including the 1936 United States Eastern Alpine Ski Championships . Although the Thunderbolt Ski Trail is currently closed to hikers due to erosion concerns , the challenging Bellows Pipe Trail runs parallel to it in many places , allowing hikers to simulate the steepness of the ski trail without actually walking on it . The Bellows Pipe trail leads from a trailhead on Gould Road to the top of the mountain , culminating in a final ascent to the summit ridge . The trail is 6.5 miles long “ out and back ,” and it is best to visit the trail from the months of April to November . Visitors are advised to follow the “ climbing trail ” signs to ensure a safe journey .
Ghost , Shadow & Phantom Trails at Pittsfield State Forest Pittsfield Department of Conservation & Recreation To continue your tour of Berkshire County ’ s most renowned backcountry ski trails , head to Pittsfield State Forest . To reach the Ghost , Shadow , and Phantom ski trails at Pittsfield State Forest , leave your car at the parking area at Berry Pond Circuit Road and proceed towards the adjacent trailhead . It leads to the Interpretive Trail , which then connects to the three ski trails after about a half mile . The Ghost , Shadow , and Phantom ski trails were built by the CCC and were used for ski races during the 1940s . Each ski trail is a little less than a mile in length , and all three have steep and relatively challenging terrain . The trails are open for skiing , but there is no lift service . An extensive network of mountain bike trails can also be found at Pittsfield State Forest as well .
Laura ’ s Tower and Beartown Ski Area Lee and Stockbridge Department of Conservation & Recreation and Laurel Hill Association Hikers will find epic views at Laura ’ s Tower , which is easily accessible via a trail from a trailhead on Park Street in Stockbridge . After proceeding up a steep and curvy 650-foot ascent , visitors will find panoramic vistas of the surrounding mountains , including a remarkable view of Mount Greylock to the north . Those who wish to return to the Park Street Trailhead can turn back to complete the 1.8-mile “ out and back ” hike . Hikers interested in a memorable hiking tour of one of Massachusetts ’ most legendary ski resorts should continue eastward on the Beartown Mountain Trail . This moderately challenging , 2.1-mile one-way , 4.2-mile “ out and back ” trail cuts through the former site of Beartown Ski Area , which was built by the CCC . Beartown Ski Area operated until 1966 and attracted hordes of ski tourists to the region during its commercial heyday in the early 1950s . The history of this site is visibly evident in the tree lines of the old ski trails , one of which connects directly with the
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