Middletown Trails and Maps

1502 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 85 trails covering 644 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

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

Sullivan O&W Rail Trail

O&W mountaindale - ferndale

September, 2025 by kaiser

Nice scenic ride . The mountaindale side goes through several abandon like towns nice ride mostly dirt / cinders / crushed stone lots of nice scenery for about 3 miles then you end at the Neversink River where a bridge is out so you have to pedal 7 miles via road to hook up on the Fallsburg side which is paved ,nice trail for 4 miles . Would do again , tables , benches and bike tool areas . No road bike for gravel part

Accordion

Pompton Valley Rail Trail

beautiful new trail

September, 2025 by krawiec.monica

Awesome trail, I tried inline skating and I wouldn’t recommend. It’s definitely possible but not enjoyable. I feel like everything else is doable.

Jones Point Path

Bad shape currently!

September, 2025 by bsmith4_tl

Took a ride on this once nice restored short trail yesterday. The state needs to get back in there and do some basic maintenance. The overgrowth of weeds has turned this into barely a single track lane. Many limbs and broken fencing. It's a shame after all the time and money put into it a few years ago.

Old Croton Aqueduct Trail

OCA south end

September, 2025 by kaiser

Interesting ride did it on a hybrid not a bad ride . Rode from Tarrytown to the end south a few places to get a bite and drink however did not see any porta John’s . Some old stone houses , walls some views of the Hudson River a must see Untermyer park & garden area .

Saddle River County Park Bike Path

Heads up that ALL e- bikes are now banned in ALL Bergen County parks. Speed limit of 10mph for all (remaining) vehicles. ¿¿ Bummer.

August, 2025 by acahilly

Heads up that ALL e- bikes are now banned in ALL Bergen County parks. Speed limit of 10mph for all (remaining) vehicles. ¿¿ Bummer.

Walkway Over The Hudson

Walkway Courtesy

August, 2025 by wayne7532

Yes Walkway is wonderful, just one problem Cyclist Courtesy.
Have rode and seen a lot of cycling after 60 years, but never the lack of cycle courtesy that takes place on Walkway. Cyclist not letting one know that one is passing on left, or better yet on right, speeding, limit is10 mph. This is not just happing to slower cyclist but also when passing pedestrians. This also applies to the new E Bike presidents.

Sussex Branch Trail

diverse & well maintained

August, 2025 by kjfhall61

The trail is ~ 20 miles in each direction. A good mix of paved, gravel, dirt — with minor sections that are “single track”’ish.

Hudson Valley Rail Trail

Great connector trail from New Paltz

August, 2025 by ddylla

This is a great paved trail that connects New Paltz to the Walkway Over the Hudson and then to the Dutchess County Rail Trail. Done together, you can ride for well over 60 miles if you want. The Hampton Inn in New Paltz is a great place to stay with the trail starting just across the street. The hotel also provides easy access to the Wallkill Trail.

Heritage Trail (NY)

Nice trail. Poor signage in Goshen

August, 2025 by ddylla

Overall, a very nice paved trail that’s well maintained but very poor connectivity and signage in Goshen. If not for that poor connection, I would have rated this trail five stars. Well worth checking out and hopefully Goshen will improve that stretch in the future.

D & H Canal Towpath

Lovely little trail

August, 2025 by nvpierro

Perfect for my elderly dog since we have not been on long walks for the past year. Beautiful scenery of the river, geese flying close to the water, a place to let your loved dog get close to and into the water, and places to sit and just enjoy nature!! Great for MAHA 15 minute walks!

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Accordion

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