Explore the most popular trails near Woodbury with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

hiking

trail running

forest

Woodbury, New York Map
VIEW FULL MAP

Rules be damned! I took my 20 lb on a leash on a late afternoon Saturday hike. Had to avoid a few bike riders but no one outwardly complained about a dog on the trail. However, the trails are very narrow in many places so you have to be on the ball to avoid getting run over by cyclers. There weren't too many though considering it was Saturday. We only did 2.85 miles because it was easy to get lost. There are a lot of other trails crisscrossing the main trail so it's easy to get off the beaten path even when using GPS.

Overall it's a fine trail and I will definitely be back to do the full 4.3+ miles.

Great trail

hiking
2 months ago

It's a great trail. Definitely some elevation changes.

Hiked this on Memorial Day with kids and our fearless terrier. Very easy family hike. Beautiful and quiet, hardly anyone around, in fact. A shout out to the kind young couple at the lean-to who alerted us to a substantial timber rattlesnake basking on a ledge maybe 40 ft from the shelter. Really cool encounter (will post pic). Will try and overnight next.

Very nice hike to Stockbridge Shelter. Took only 40 minutes walking casually with 40-pound bags. Saw a rattle snake in a rock crevasse towards the top about 50ft away from the shelter.

Parked at Silvermine and took the yellow-blazed Menomine trail across silver lake drive and made a right onto the green trail at the first 4-way trail intersection to get to the shelter.

Nice Trail, mostly mountain bikers who may have been pissed off that we were walking through the trails.

walked the first half from Jericho tpike it is a bit shabby. lots of garbage. would make a nice eagle scout project to clean it up.

Walked this trail 2 days ago. It was absolutely lovely but the trail was confusing in a number of spots. The trail could definitely have been marked clearer but overall it was really pretty and relaxing. We would recommend this hike; make sure to leave yourselves 2.5 hours to complete if you're hiking.

Love these trails! Challenging and close to home. Never get tired of a fun ride here

Followed white and yellow trails, both of which were pretty well marked--which may change as foliage fills in. Yellow path easy, with gently undulating terrain. In the woods themselves, there were areas that were very steep. Patches of ice in low lying areas, some areas were becoming muddy as the temperature was warming above freezing. Looking forward to returning in the spring (and with a map)!

I did the Cold Spring Harbor portion on some random October day. It was awesome! This part is hilly, so be prepared!

hiking
6 months ago

Easy

mountain biking
8 months ago

Great trail

hiking
8 months ago

The trails are not all well marked and you have to be careful of bike riders, but nice trail overall. Not super challenging terrain for hiking.

Beautiful trail. A decent workout, but not too challenging if you want to just enjoy yourself. Really enjoyed it and will take the dog along next time.

mountain biking
9 months ago

Awesome trails in Long Island from moderate to hard

This trail was a wonderful surprise as I was visiting family and a nice way to find time for myself. I hike a lot in Wisconsin so I think the moderate rating is correct. The trail is beautiful, nice ups and downs, and perfect length at 7.1 miles. My only gripe is that without the app I would have been in big trouble. The trails intersect and are not well marked, the app was the only way to know which way to go and not get lost.

mountain biking
11 months ago

Great trail
So much fun

mountain biking
11 months ago

Great trails with many different paths to keep it interesting. The black trails were too difficult for my son and I but the blue and green trails were awesome. We rode approx 9 miles in 4 hours. Fantastic Sunday!

Sunday, June 25, 2017

This trail sucks! Good luck following directions to trailhead. The section we walked was extremely narrow and unkept. Chigger town!

trail running
Thursday, June 15, 2017

hiking
Wednesday, May 31, 2017

Actually started at Cold Spring Harbor and went down to Massapequa Park for a total of 19.3 miles. It's a pretty interesting trail. The north side of the island is very hilly, but from middle island downward it's all flat. I grew up on the island and never noticed there were trails running along some main roads and behind people's houses. I don't think there are many places you can experience trails like these. Of course due to the proximity to cars, houses and people, it's anything but serene, but it's a fun goal to accomplish. It took a little less than 8 hours to complete.

hiking
Wednesday, May 31, 2017

Very nice in the fall!

Great spot

mountain biking
Wednesday, April 19, 2017

Loved it. 4 stars for some forks in trails not being marked. Followed the most difficult trail markers. Had some technical spots but overall great spot. Will be riding again soon.

Sunday, April 16, 2017

Nice place for mtb ....

Saturday, April 15, 2017

This map doesn't show the entire trail. It starts in Massapequa

hiking
Thursday, February 23, 2017

I began in Massapequa, and have been covering about 5 miles per day, with a return to my car. Each day I found an adequate stopping place, where I could drive to and then pick up the trail, until today. I am probably going to start from the end of the trail and hike to my finishing point today and back to my car. There are a few places were the markers are confusing.

Thursday, November 03, 2016

Great hike! The trails coincide with the Nassau/Suffolk greenbelt trail. Plenty of hills and scenic views. I was surprised of the many people hiking and biking these trails.

hiking
Thursday, October 06, 2016

This was a great hike for me and my dog. The trails are better suited for biking however we enjoyed them a lot. Definitely worth going back to again!

Load More