Explore the best rated trails in Old Chatham, NY, whether you're looking for an easy walking trail or a bike trail like the Mass Central Rail Trail and Wallkill Valley Rail Trail . With more than 46 trails covering 679 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.
The surface is paved, and in excellent condition.
The trail is ever so slightly down hill from north to south.
Mostly shaded, and while not amazing scenery, it is a lovely trail. In spring, when sunny, watch to LOTS of turtles on the far bank of a swampy section near the cheshire reservoir (on the west side of the trail)!
IT had great views, history and parking. Stopped and had our lunch in a quiet spot overlooking the water. Saw a Bear ¿ at one end..he didn’t catch us :)
Currently there is a couple of sections that are really nice for the work thats been completed, but will be a fantastic trail once they have completed the sections necessary to connect them into one long trail. All the sections completed are mostly all paved and are great for walking/jogging/biking & wheelchair/stroller friendly. The only exception is tgr Naugatuck River Greenway section that starts at the Sullivan Senior Center, which has a paved trail that runs parallel to the the river and ends at the side road which you continue down a one way street that almost zig zags until you reach palmer bridge. Crossing the bridge and crossing to the paved trail that goes behind a condominium and continues until the end of the dirt parking lots (trail is paved) of John Toro Sports Complex, where the pavement ends towards the actual field. Then it transitions to the field with no defined trail. The Trail at that point isnt really distinct. I lived here most of my life and I didnt know until I saw a news article about The Rainbow Bridge and found that the trail in fact extended past where the pavement ends and continues straight past the dog park past both the first baseball field, the soccer field, and then about halfway through the 2nd baseball field there is a wide opening in the forest, where you then see the entrance to the Rainbow Bridge Trail. Which is an amazing small half looped trail, with some of the most beautiful works of art, and tributes to various pets (photos, stepping stones/memorial rock garden, a memorial fence, k-9 officers memorial bulletin board(s), sculptures, poems, signs, chairs, then the rainbow Bridge which is adorned with photos, momentos, stories, collars & tributes to pets of those who came to place their beloved pets memorials. After you find the exits shortly after that you can see the wide open pathway continues for a while on but ends at a fenced off area that currently is a business/underutilized "Sports park" that will eventually be replaced with a connector trail that will connect with other nearby trails.
.With a mix of cinders , gravel , dirt & pavement this makes for a nice interesting ride . Along the way in High Falls make a left and visit the D+H canal museum its about a mile down the road . Once you venture a mile and half through a grass area the trail stops however pedal straight out on to Lucas tpk & make left onto 209 then left on main & right on scenic you will then pick up the trail to accord
Rode 2.5 miles from Wilmington north on mountain tire bikes and it is doable but rough with roots and rocks. Nice bridges but missing signage in some areas, others well marked. No washout areas close to Wilmington.
Morning ride, foggy with lots of little critters, trail is paved with a few hills, views of railyard, picturesque village of Round Lake, mostly forested with wild flowers, very well maintained rail well worth the ride. trail.
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.
Settle grade difference between start to finish. All paved smooth.No bugs.Crowded with walkers, skaters, and bikers.Windy in the afternoon.
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.
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