Explore the best rated trails in Stockbridge, MA, whether you're looking for an easy walking trail or a bike trail like the Albany-Hudson Electric Trail and Black Bridge Trail . With more than 55 trails covering 768 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
Parked at northern end just S of Orphan Farm Rd, NY; Trail surface is outstanding including numerous portions of elevated sections over wetlands. Did not see much in the way of wildlife. Quite rural with the 1st p potty 10 miles south; Turned back at Millerton; Shade 50% or so.
Update to my 8/2024 review: Remains a TOP trail; At northern end easy parking at the Adams Visitor Center; Saw many signs of beaver activity - dams and huts - but no beavers. The Appalachian Trail crosses at Church Road in Cheshire; At southern end I turn back at the Crane Ave. parking area as, in my opinion, there's not much of interest in the remaining mile or so.
Great ride through the shawingunk mountains ! Trail was great bikes were awesome ! What a beautiful day !!
Haven't ridden the trail since 2023. Rode from Cheshire down to New Haven, Saturday July 19th. Absolutely awful; entire section needs repaving and upkeep. Constant cracks in pavement and much debris on surface; plus glass and homeless down by the Wharf. Connecticut should take notice from Mass and NY on trail up keep. Both states's trail are far superior to CT. Also, difficult to navigate at trail end in New Haven if you don't know the city; poor signage.
did trail 7 years ago. What a change!! Smooth all the way from Copake Falls to Wassaic!!!! Did 50 mile round trip then took a dip in the spring fed lake at Taconic Hills State park. Can walk to the lake from the trail head at copake falls. Also a nice state park with interesting sights. We stayed in Great Barrington , 10 miles from Copake Falls. Make sure you check out the Barrington Brewery. Great beer, great food.
Beginning perhaps 2 miles north of the Simsbury Airport and continuing north for at least a few miles the trail will be closed for construction (looks like repaving + ?). I was on this trail yesterday and the "Will Be Closed" signs are abundant.
Rough in spots but really nice ride !!! Would do it again ! Tough around the steep hill x2 , Tressel bridge !!! But nice scenery and cool breeze Pat and Kevin B
Section from New Paltz (and maybe a mile or two below, I haven’t checked) to a mile or so north of the Rosendale Trestle is superb. Just after the Women’s Studio Workshop is an interesting historical furnace chimney. But then the trail comes apart - chunky gravel and hills I wouldn’t want to come down, leading to Williams Lake (saw lots of landscaping going on but no one using that end of it recreationally). I returned to the Women’s Studiovia the road.
Love the scenery. There are plenty of rest areas.
Beautiful trail. Well maintained. Headed west from Henrietta first, a little secluded. Only went about 2 miles then headed east to lock 33. Felt safer going east. Full of exercise traffic… love to see that!
I rode this trail from the Northern tip south about 10 miles and back. It was very smooth pavement, a well marked trail and delightful views.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
