Middletown Trails and Maps

1512 Reviews



Looking for the best trails around Middletown?

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.

Recent Trail Reviews

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.

Accordion

North County Trailway

Smooth riding, lovely view- part 2

November, 2025 by kleistikow

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.

North County Trailway

Smooth riding, lovely views

November, 2025 by kleistikow

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.

Sussex Branch Trail

Great For Fall Foliage

October, 2025 by 7zwbq79645

The trail is well maintained. Mostly passable with gravel bike except a small portion around Andover. The section around Andover is also hard to navigate.

Columbia Trail

¿¿ NJ RtoT. GEM of a trail !

October, 2025 by toddburrparts

Riding popular trails in each state Metro, New York area and NE. This trail was above expectation. Well maintained mix of packed gravel to packed stones. All wide capable of handling traffic and any type of biking running and some equestrian.. surprising mix of landscape from River Gorge to large animal farms. Lots to see highly recommended. Road from Bartley Road to Hoffman’s. Entry point Long Valley, Apple parking and food available quaint town.

Sullivan O&W Rail Trail

roots and railroad ties

October, 2025 by bettysaar

We decided to start across from the winery, and end our trip there. We went one way and hit roots and railroad ties immediately. We turned around and got the same. Needless to say, the winery was great. Would be a perfect hiking trail. It was beautiful.

West Essex Trail

West Essex Trail experiences

October, 2025 by lisefvail

I walk on this trail for 1 1/2 hours every day. It’s lovely, varied, not difficult at all. A former rail line, so it’s relatively even terrain. I see deer most days, and cross two bridges—over Route 23/Pompton Avenue and the small Peckman River. I park at the Cedar Grove Community Center, and walk up to the trail. Best time of my day, every single day. Really love how healing Nature here is.

Heritage Trail (NY)

well maintained , interesting sites, and views along the way.

October, 2025 by toddburrparts

I rode from Harriman to the edge of Goshen. Nice smooth, pavement with little or no bumps. I found some interesting sites and information along the way. I will return to ride the second half of this heritage Trail.

O&W Rail Trail (Ulster County)

O&W Kingston - Kerhonkson

September, 2025 by kaiser

.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

Parksville Rail Trail

This trail is lovely there's a little water fall halfway through it we're the railing is and its beautiful

September, 2025 by fay.ridgeway05

This trail is lovely there's a little water fall halfway through it we're the railing is and its beautiful

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Accordion

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