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.
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.
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 .
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.
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.
The ‘protected bike lane’ is more like a highway breakdown lane, but separated by a guardrail. Again, not pretty, but it is a safe and efficient way to get from Point A to Point B.
We parked at northern end of South County trail, Elmsford, and turned around at mile 33 marker, Shenorock. Paved trail is perfectly maintained, beautiful foliage. The next time we would park at New Castle, however, to avoid rush hour traffic smells and sounds of Saw Mill River Parkway and Route 87. Both are quite close to trail. The Elmsford-New Castle section also has portions where trail leaves woods and is essentially in protected bike lane along county roads. Not pleasant ruding, although certsinly efficient wat you bike from Point A to Point B. These trails are seamlessly connected, leafing to MYC.
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