Looking for the best trails around Port Chester?

Explore the best rated trails in Port Chester, NY, whether you're looking for an easy walking trail or a bike trail like the Norwalk River Valley Trail and Ridgefield Rail Trail . With more than 96 trails covering 635 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

Hamburg Mountain Wildlife Management Area

Amazing 3 mile rugged old rail trail ¿,you need a MTN bike ¿ and there's a washout half way down ¿ but it's beautiful ¿

February, 2024 by petemcgill6969

Amazing 3 mile rugged old rail trail ¿,you need a MTN bike ¿ and there's a washout half way down ¿ but it's beautiful ¿

Loantaka Brook Reservation Trail

Nice but icy

February, 2024 by hrowan1029

We went to this trail, beginning right next to Seaton Hackney Stable, because we knew it had a paved path and we had a lot of snow. We didn't know the trail would be covered with ice and snow and after a very short walk we decided it would be wise to turn around before one of us fell. We intent to go back when the weather gets warmer because it's a beautiful park and trail.

Old Erie Path

Hidden Gem - caution in Sparkill

February, 2024 by jeffrey.r.schmoyer

Old Erie is a unique and lovely gravel path distinct from the Clarke and Esposito paved trails. Easy to miss but very worthwhile IF you have the right bike. Somewhat chunky gravel and a few ruts so recommend at least 38mm tires. In exchange for bumps you get forest, nice elevation changes, beautiful views of the river, and a direct path connect to both downtown Nyack (shops, eats) and the new Mario Cuomo bridge path. But VERY important: the start of trail in Sparkill is a very dangerous 5-way intersection with blind spots... DISMOUNT here, wait, listen, walk it across.

Accordion

Shore Parkway Greenway Trail

Shovel & Ropes needed

January, 2024 by garyemccusker

Total Mess Do not waste Your Time

Ocean Parkway Coastal Greenway

Nice and long bike path

December, 2023 by kzhang20000

During the summer, there are more than 2 stops along the way you can buy drinks and food.

27 mile total. On my way back, I was riding against the wind, so tired......

Vanderbilt Motor Parkway

It's not bad

December, 2023 by kzhang20000

It's not too long, but watch out for sharp turns and steep climb onto the cross over bridge.
Also there were junkies in the Allie pond park parking lot asking people for money.

William R. Steinhaus Dutchess Rail Trail

William R. Steinhaus Dutchess Rail Trail

November, 2023 by thejake91739

After starting in New Paltz on the Hudson Valley Rail Trail and then crossing the Walkway Over The Hudson, I continued on to the Dutchess Rail Trail. I only went a few miles before turning around and heading back to New Paltz for a 21 mile ride.

The portion I rode is for the most part heavily forested, so if you like colorful trees in the fall or shade in the summer you'll love this. The trail is easy to ride, in amazing condition, and on a weekday morning in mid October lightly used. I especially appreciated the use of wood fencing in many spots which was the perfect architectural touch for this trail. Another highlight was Morgan Lake with its lovely swans and colorful trees reflecting upon the water.

I wish I would have had the time to venture further into the beautiful rural areas, but time was of the essence. I guess I have a reason to return and do the full length next time!

Vanderbilt Motor Parkway

Entire trail now reopened, repaved, with historic signs

November, 2023 by tom0153

The history of the Long Island Motor Parkway (as it was first recalled) is revealed with signage along the length of the Parkway, including the site of the Jacob Johnson Family Burial Ground who appears in the 1830 Census as a "free colored man." At least two of his sons served in a segregated unit in the Civil War. He was a farmer in the area until retirement when he lived very close to Alley Pond.
The length of the entire park roadway, designated as part of the Greenway, has been repaved.
Review other park features when you come. In another area of the larger Alley Pond Park is found the oldest and tallest tree in NYC, already growing at the time of George Washington, known as the Alley Pond Giant. Hiking trails throughout the Park are well maintained.

Maybrook Trailway

Partial Trailway closure

September, 2023 by steve.schwinn

This is still a great trail but currently (9/2023) the Trailway is closed between the Stormville parking area on South Green Haven Road and the road crossing at Depot Road due to a partial washout (see pic).
There is a bypass using Route 216 (busy and not always good shoulders).
People have gone around the barricades and used the Trailway. Please use caution if you do so.

William R. Steinhaus Dutchess Rail Trail

Hopewell Junction start on WRS Dutchess Trail

September, 2023 by bsnicholson63

Very nice 7 miler tonight just before sundown. Trail was very clean and only lightly populated as we headed south for 3 1/2 miles and then back to the parking lot.

Too bad that Daddy O's had closed their kitchen when we returned. Had to go to the Redline Diner to get a post-ride meal on a Sunday night.

Road crossings were well marked and use automatic yellow flashing lights for traffic to be aware of bikers approaching the crossing. A nice feature.

Pequonnock River Trail

The bridge is repaired and the trail is open.

August, 2023 by bliebow1234

The bridge is repaired and the trail is open.

Heritage Trail (NY)

from Harriman

August, 2023 by dagpl8

Was a great great trail! Got a little lost through Goshen, thank you kind gents for allowing us to follow you to the connection!

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Accordion

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