Explore the best rated trails in Peekskill, NY, whether you're looking for an easy walking trail or a bike trail like the Wallkill Valley Rail Trail and River-to-Ridge Trail . With more than 116 trails covering 812 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.
Easy access, clean blacktop and nearly unlimited distance in either direction! Outside of the Morgan Park entrance this is the best bet!
Decent walk and view. As of October 2026 bathrooms are not open ever.
Rode Pawley Trailhead to Hopewell Junction and back. Perfect, smooth, clear, pavement. No downed trees . Few easy road crossings, shady throughout. Nice lunch at Daddy Os in Hopewell Junction.
We did this trail in two days. We learned that it is not quite complete from Hillsdale to Wassaic. Trail is closed from Black Grocery Road to Orphan Farm Road about 1.5 miles. So be warned that as of Sept 15 you can’t quite go completely through YET. Above Millerton and below are almost two completely different trails so we were happy to be able to stop and explore at our leisure. Above is really farm and marsh lands while below has more towns and historical things to see and do. Millerton, has many places to eat and a great mid stop. The leaves are not turning yet but will be beautiful in the colorful fall. I heartily recommend the ride.
Mostly paved and tree covered. Will try bikes next. Is there a way to track miles covered?
Reviewing for biking. No as long as it says…and you need to cross the streets a few times. Also lacking good signage.
It’s perfect for people who love nature—lots of forest and good trails. I really liked it.
I’ve gone a few times to ride my bike however I’ve almost got taken out by people on racing bikes and think they are in a triathlon..not cool
Rode entire trail roundtrip on a sunny August day. It's a great trail with a great paved surface. Scenic, too. The southern trailhead (Wassaic) has a direct train connection to New York City, so it's just a matter of time before it's discovered by folks from the city for a day's ride.
Town of Millerton in center of trail had the best facilities for a mid-ride break. Copake Iron Works Museum at Taconic State Park and close to the trail also well worth a visit.
The trail is primarily shaded with a few places that are not. You are mostly surrounded by trees, with only a couple of bridges or water views. It’s nicely maintained packed gravel. Keep a watch for the signs that tell you where the poison ivy is.
Cute park area, playground for kids, pavilion, picnic tables, grills. Boat launch and museum, although the museum had a sign that it is no longer open. I parked at the visitor center and biked the Heritage Trail. Easy, gravel, a couple of ponds along the way. Ends at 209.
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