Explore the best rated trails in Middletown, 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 84 trails covering 647 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.
Very scenic good ride , if your biking I would recommend ride early otherwise you encounter many walkers , strollers etc which can be a hazard if you are biking and cone around a corner the a surprise.
Nice trail to get in 10 round trip , scenic , rest areas , food .
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)
I disagree with the description that this trail is packed enough for skinny road tires. There are parts with thicker gravel and I was glad to have gravel tires on my bike and even then it was a bumpy ride. Nice scenery, not too crowded, good bathrooms. Overall loved it.
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.
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.
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.
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 .
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 :)
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 .
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