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 Fairfield Hills Campus Walking Trails and Norwalk River Valley Trail . With more than 101 trails covering 695 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.

Best Trails in Port Chester

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Showing 0 of 101
1 Review
Battery Bikeway

The Battery Bikeway is a only a half a mile long but it is an important link in the Manhattan Waterfront Greenway system, connecting the...

Length: 0.5 mi
State: NY
Surface: Asphalt
0 Reviews
Beach Channel Drive Greenway

Although just a mile long, the Beach Channel Drive Greenway in Queens offers expansive views of Jamaica Bay and the beautiful Marine...

Length: 1 mi
State: NY
Surface: Asphalt
8 Reviews
Berkshire Valley Management Area Trail

The Berkshire Valley Management Area Trail passes through hardwood forests and affords views of the valley below to the right. Equestrians...

Length: 2.1 mi
State: NJ
Surface: Ballast, Cinder
46 Reviews
Bethpage Bikeway

The paved 13.4-mile Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban...

Length: 13.4 mi
State: NY
Surface: Asphalt
10 Reviews
Boulevard Trolley Line Path

This 2-mile long paved path runs directly adjacent to (about 30-40 feet off of) the Boulevard in Mountain Lakes, NJ, and follows the exact...

Length: 2 mi
State: NJ
Surface: Asphalt, Concrete
5 Reviews
Briarcliff-Peekskill Trailway

The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain...

Length: 12 mi
State: NY
Surface: Asphalt, Dirt, Grass
34 Reviews
Bronx River Greenway

The Bronx River Greenway runs for 22 miles along the Bronx River, traveling from the mouth of the East River north to the Kensico Dam,

Length: 22 mi
State: NY
Surface: Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel
13 Reviews
Derby Greenway

Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural...

Length: 1.97 mi
State: CT
Surface: Asphalt, Dirt
11 Reviews
EPCAL Alternative Transportation Path

The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s...

Length: 9.28 mi
State: NY
Surface: Asphalt

Recent Trail Reviews

Maybrook Trailway

The Weeds Are Gone

August, 2025 by robertgerry

I just rode the trail today and the weeds mentioned in a previous review have now been mowed and the tree leaning across the trail near Whaley Lake has been cut. The trail is now in excellent condition with none of the typical rail trail root bumps encountered today. BobG.

North Shore Rail Trail

Love the trail, but.............

August, 2025 by pawerfel

Great trail, ride it frequently with my wife. Good workout for 22 miles. Main issue is not the road crossings; we ride many trails with more crossings than this, but on those, the towns take down the brush and you can see cars approaching the intersections. On this trail, you pretty much have to stop and inch out into the road to see these cars, many of whom are not "impressed" by the flashing yellow lights that you need to push a button for. Many drivers are looking at their phones rather than the road these days. You must appraoach these intersections as if you are invisible. Be safe

Maybrook Trailway

Great Ride!

July, 2025 by douglas.klion

A friend and I did this ride today starting from Brewster to Hopewell Junction, continuing on the Dutchess Rail Trail for ~4 miles and back. The ride was excellent, a little over 50 miles with a gradual decent (~10 miles) on the way to Hopewell and ascent back. The trail was very smooth, there were a couple of spots on the Dutchess side that had growth into the trail and one downed tree blocking the way.

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