Explore the best rated trails in Ashley Falls, MA, whether you're looking for an easy walking trail or a bike trail like the Albany-Hudson Electric Trail and Ashuwillticook Rail Trail . With more than 62 trails covering 834 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.
Yes Walkway is wonderful, just one problem Cyclist Courtesy.
Have rode and seen a lot of cycling after 60 years, but never the lack of cycle courtesy that takes place on Walkway. Cyclist not letting one know that one is passing on left, or better yet on right, speeding, limit is10 mph. This is not just happing to slower cyclist but also when passing pedestrians. This also applies to the new E Bike presidents.
June 6th 2025
The Mrs and I rode this beautiful trail from North Hampton to just short of Belchertown, and back.
The weather was great and the trail is mostly shaded, so the ride was superb.
I'd have no objection to doing it again.
This is a great paved trail that connects New Paltz to the Walkway Over the Hudson and then to the Dutchess County Rail Trail. Done together, you can ride for well over 60 miles if you want. The Hampton Inn in New Paltz is a great place to stay with the trail starting just across the street. The hotel also provides easy access to the Wallkill Trail.
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.
I just rode the trail today and the weeds mentioned in a previous review have now been mowed and the tree leaning across the trail near Whaley Lake has been cut. The trail is now in excellent condition with none of the typical rail trail root bumps encountered today. BobG.
Awesome ride !!! total 24 miles just breathtaking !!! Trail was wonderful mostly flat , busy with walkers and bikers all friendly !! Pat &Kevin Bennett
A friend and I did this ride today starting from Brewster to Hopewell Junction, continuing on the Dutchess Rail Trail for ~4 miles and back. The ride was excellent, a little over 50 miles with a gradual decent (~10 miles) on the way to Hopewell and ascent back. The trail was very smooth, there were a couple of spots on the Dutchess side that had growth into the trail and one downed tree blocking the way.
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.
Use gps route its not well marked like others have said but part of the fun was planning the route and then finding your way as you go.
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