Looking for the best trails around Crompond?

Explore the best rated trails in Crompond, NY, whether you're looking for an easy walking trail or a bike trail like the South County Trailway and Old Croton Aqueduct Trail . With more than 114 trails covering 859 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.

Recent Trail Reviews

Rahway Valley Rail Trail

Embryonic!

June, 2026 by leftahead

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.

Farmington Canal Heritage Trail

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.

June, 2026 by taccuosti

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.

Ashokan Rail Trail

Quiet, peaceful, looking for a different perspective in life, these trails will definitely will. The Red trail leads to the science parts of the Hudson. The blue trail goes all around the large pond which is also beautiful.

May, 2026 by z4fold01

Quiet, peaceful, looking for a different perspective in life, these trails will definitely will. The Red trail leads to the science parts of the Hudson. The blue trail goes all around the large pond which is also beautiful.

Accordion

Farmington Canal Heritage Trail

Terrible Shape

May, 2026 by dave36

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.

Bethpage Bikeway

Bethpage to Jones Beach

May, 2026 by mx546x87dm

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

Highlands Rail Trail

Awesome surface!

May, 2026 by mythreesonsccb

This rail-trail is terrific! I use an electric scooter so the surface is important and this blacktop was easily navigable. At one end of the trail is an Irish pub for a fun meal stop- we turned around there to Irish music right after St. Paddy’s Day. Park at Dody Road Haskell. Length was great for us but you may want a longer ride/walk.

Hudson River Greenway

A great ride over the GWB to Hudson

April, 2026 by kaiser

Started in FortLee Nj , biked over the GWB took a few roads to get to the Hudson greenway . The venture was very picturesque throughout the entire ride , many things to see & do . We ended up going to Chelsea and 505 W 23 rd st to a very nice place to grab a bite & water at the Wildflower . I will do again .

North Shore Rail Trail

Not plowed

February, 2026 by polecatwillie

Why has this trail not been plowed?? It has been snowed over since December.

Ashokan Rail Trail

Views, History and nice bike path

December, 2025 by tombegg14

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 :)

Joseph M. McDade Recreational Trail

Addition to very picturesque trail

November, 2025 by kaiser

The trail from Milford start point is on k for a few miles but turns to a rocky narrow trail not suitable for a bike , Start at Conashaugh trail head there is only 1 area where you have to walk down 1 set of stairs and go up another otherwise it get great .I wanted to add although I was able have a good ride on my mountain bike I would not recommend the use of any road bike .

Joseph M. McDade Recreational Trail

Very picturesque good trail .

November, 2025 by kaiser

This is a good trail & I would have enjoyed more if it were warmer and I did not ride in gale force winds. Bikers do yourself a favor from Milford grab a bite or drink as you have no food or drink areas until the end unless you ride when Dingmans campsite is open , you may get something there . Proceed 209 S to Conashaugh trail head unload and go south from there you will have about 18 miles to the end.

Ashokan Rail Trail

One of our East coast favorites

November, 2025 by kleistikow

We biked on a Sunday in May. Plenty of parking at West Hurley. The scenery was stunning and varied. Started in forests, with some reminders of people who made their living in these woods. Ended with views of Catskills and the reservoir. Truly stunning views, wide, well maintained trail that we cycled on our hybrids.

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Accordion

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