Find the top rated inline skating trails in Ossining, whether you're looking for an easy short inline skating trail or a long inline skating trail, you'll find what you're looking for. Click on a inline skating trail below to find trail descriptions, trail maps, photos, and reviews.
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Mostly cinder. Started from access lot off of RT 7. Shared RT Trail with the Town Of new Milford. Parallels an active track. Good variety of terrain and scenery..
Have a comfort bike with wider tires 24 speeds. There are in most parts of the trail 2 tracks. Mostly unkept so poor for biking. Trail is grass and like I said 2 bike tire tracks. However would be great for hiking.
Nice trail to get in 10 round trip , scenic , rest areas , food .
Wonderful trail. Part of the larger Empire State Trailway. This part from Eastview to Baldwin Place is the section I ride the most. Mostly shaded once you're north of Millwood with plenty of spots where you can stop for a bite or veer off for road riding near the reservoirs.
My wife and I walked the trail after dinner tonight. It’s a fine 12 foot wide trail, very well maintained and great for moms running with strollers or teaching kids to ride a 2 wheeler. Too short for a serious adult bike ride and it’s not terribly scenic but it’s nonetheless a nice addition for the community. It does lack mileage markers which would be helpful.
The trail is not accessible for a 3-mile stretch. From Green Haven and then Eastbound is impossible to pass. Trees have fallen down virtually every 50 yards blocking passage. I carried my bike past about 6 trees and each time I saw another tree blocking the trail. I came across a clean up crew that told me the downed trees went all the way to Green Haven. I was 3 miles east of Green Haven when the mess started. There is also debris along the entire section which I was fortunate not to get a flat tire. The cleaning crew told me they have only 4 people and they will try to hire a contractor to clear the trees. There is no way a crew of 4 people could handle this. It would take them months to clean it up. (July 10, 2026)
The Trailways Bridge over the river in Brewster is open, eliminating the on-road detour. The eastern end is currently at the NY/CT line at Farrington Woods (with trail parking) in CT. Long range plans are to develop the CT portion of the RR path to Danbury.
There are far more legit parking areas than currently shown on TrailLink. Services are few and some might seem close lack easy access from route to road. High point is Whaley Lake. The trail is in good condition for it's entire length.
This isn’t a trail in any real sense, but is clearly intended to be the entrance to a more ambitious path along the now-overgrown elevated rail line leading away from Summit. It’s literally a few hundred yards that ends in a locked gate. Nothing to see here unless you’re being a radical completion key for every trail listed in the app. 2 stars for potential, here’s hoping there’s some further expansion somewhere in the works.
Rode Simsbury down to Plainville. Simsbury to Avon was full of tree root bumps, and lots of branches & trail debris. It's almost as if Simsbury wants to keep cyclists out. ¿ However, Avon and Farmington were great rides, as was Plainville.
Rode from Avon, CT to Westfield, MA. Mass section in great shape. CT section is awful. Pavement is split, constant 'ka-thunk', pot holes not marked, just horrendous condition. Where is the CT DOT and our tax dollars? Stay away.
I did this route many times. About a half mile West from the South End of the Bethpage Bike Path ie,. Merrick Road NY 27A, you’ll see the Wantaugh Parkway entrance to the Jones Beach path. way back when they couple
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