Explore the best rated trails in Ossining, NY. Whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and D & H Canal Linear Park. With more than 106 trails covering 753 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.
The trail is a bit more rugged and not as well maintained as the other NJ trails, though a hybrid bike will do the job. West of Blairstown Airport there are a few short sections where you have to get off the bike and deal with steep embankments. There are also a few weird places that seem like dead ends...you come to a road crossing and need to follow it a bit before the trail resumes on the other side. They could use a little signage in these areas...having Google Maps on my phone came in handy on a few occasions.
A good starting point for the Western section is the park at 5 Foot Bridge Lane in Blairstown, and for the Eastern area there's a small lot at 106 County Rd 519 in Newton.
Don't even think of going if it's been raining in the last few days. The last time I went there I parked at the Foot Bridge Lane lot in Blairstown and headed East...I slogged through and around mud flats for a few miles before I came to an impassable one and had to turn around. You also learn pretty quickly to be on the lookout for horse calling cards.
Other than these drawbacks it can be a nice ride...people you meet are friendly and for the most part you're away from traffic noises and off the beaten path.
I mountain biked this short but beautiful trail before the 2012 Sandy washout. I took it from Ogdensburg to Beaver Lake Road (walk the tracks the last 300 feet) and then headed down RT 23 and left on 517 to Ogdensburg for a easy loop ride. I hiked the trail 1/13/2023 and I am happy to say that the collapsed section now has a narrow berm on the south side that can be biked (technical) or just walked. There are some trees down along the trail (hop some and carry over some) and some muddy areas by the rock cuts and some passable streams, but the views are worth a try. If you scramble up the rock mound you have great views of Ogdensburg and Sparta, and when you travel under the power lines you have a great view of RT 23 and Franklin. I think the rock cuts are deeper than the ones on the Paullinskill Trail and the elevated rail bed section are amazing. If you want to continue further into the Hamburg Mountain Wildlife Area, you can hop off this trail when it gets close to RT 23, and you will be across the street from their parking area. There is a also great little convenience store at the start of the trail in Ogdensburg as well a a new local bar across the street.
I rode this over two separate weekends, Once from the Wassaic train station to Millerton, and once from Millerton to almost the end of the trail. Picking a favorite section is a really hard call, they both have their pluses. One of the things I really liked is the lack of level crossings making this more of a bikers trail than a walking trail with a lot of trail where you will only see bikes for a few miles. Pedestrians are great, with only bikes there is a lot less stress about passing. I think just about every level crossing has a portalet, even the ones without parking.
Wassaic didn't offer much in the way of attractions or close by food, Millerton on the other hand had plenty to offer and explore, there is even an actual bathroom on the trail in Millerton. While it would probably be fine to bike the town, I used the rack and walked it. Lots of interesting shops and food options in Millerton so it is worth stopping. Once you head north of Millerton you are back in open land with the occasional road crossings. There is a section where you ride over a large pond on a bridge that is nice.
To add to the previous review, on 11/3 the trail was completely flooded at Jefferson Lake, just north of the Waterloo Road parking area.
We rented bikes in new paltz to go from there up past Rosendale trestle The rest was closed but that was ok. We past some interesting caves with cold air which was a nice surprise. It is finely crushed gravel which is an up grease from mud; however check your bike company to make sure your tires are appropriate for this type of gravel Definitely picturesque, quiet and peaceful Would highly recommend
Yes the path is new, surrounded by greenery and tuck back from the main road. My biggest complaint is the amount of crossroads at the beginning in smith town. Too much interruptions AND You really need to be careful even when you hit the rider alert button for crosswalks The ride itself is nice, but no facilities on path.
The Harlem Valley Trail from Taconic State Park to Wassaic (Metro North Station) spans 24 miles through beautiful farmland and marshy areas with Mountain ranges on both sides (Berkshire and Catskills). The entire trail is paved with asphalt. Unfortunately, there are older segments that sorely need maintenance, especially the roughly 4 mile stretch from Taconic State Park south. The trail is also narrow in spots making it uncomfortably close for bikes traveling in opposing directions. The trail does pass through several towns where you can find places to eat and shop.
Beautiful bike trail to enjoy the fall colors. Love it so much. Highly recommend.
This trail is well marked and is a great combination of climbing steep rocky sections and walking flat sections with decent views. For someone out of shape, this hike is a great workout with plenty of resting spots.
This trail is great despite the middle aged men speeding past you at 90 mph on their LeMonds. I’m not sure if they are bike messengers or just “has beens” trying to live out their dreams of being in the Tour De France, but their speed and shrill shouts of “Left, Left, Left!” piercing the crisp fall air can really ruin what is otherwise a beautiful and relaxing family outing.
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