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 108 trails covering 779 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.
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!
After pedaling down the Hudson Valley Rail Trail from New Paltz, I made my way onto the walkway. It was 7:30 on a brisk mid October weekday morning, and the bridge was not crawling with hordes of tourists (like me). Instead it was obviously primarily locals out jogging, getting their steps in on their walks, rollerblading, and walking their dogs.
The views are as expected - absolutely sensational and breathtaking looking both up and downriver.
After continuing across I proceeded to explore the Dutchess Rail Trail for several miles before heading back.
As luck would have it, when I returned the walkway was a completely different world. It was totally enveloped in fog, and you could no longer see the Hudson let alone fifty yards in front of you. The bridge was essentially deserted. Worst of all, I didn't get to do my selfies with a Hudson River background!
The walkway, combined with the rail trails on either end, is a must destination ride for bicyclists. What an unforgettable experience!
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.
I rode the southern half of this trail from Millerton to Wasaic the first week in October on a 75° afternoon. Beautiful ride on a beautiful day.
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.
Parked on the east side of the bridge after a bit of confusion finding the end of the bridge. Signs were a bit confusing. We just looked at the huge bridge went towards the obvious end of it to find parking. Lightly crowded on a Monday morning around 9:30 as we headed west across the bridge. Well worth the trip as the views of the Hudson Valley are spectacular! Rode 8 miles west out into central New York. Very little elevation change and a clean smooth trail. Worth the ride!
Rode the 13 miles from Orphan Farm Rd to Millerton and back. At the northern end, at Orphan Farm Rd is a large parking area adjacent to a small farm, a solar panel field and a glamping site. No one there at 8am that Saturday but half a dozen cars upon my return at 11. Likewise, I had the trail practically to myself until I neared Millerton and found it moderately traveled by later that morning. The asphalt trail was in very good condition and there are a few boardwalk sections as well, also in very good condition. The environs are beautiful with forested sections, farm fields, wetlands and vistas of the nearby hills. Not more than two miles from the north end is the Depot Deli, near the entrance to Taconic State Park, where all manner of beverages, ice cream and snacks can be found. Breakfast at Oakhurst Diner in Millerton is highly recommended. Clean public bathrooms can be found just behind the schoolhouse museum beside the trail after crossing the main street.
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.
I can't believe I'm forced to give this trail two stars. It's not due to the location, the scenery or lack of variety. The trail gets five stars for these features. It's due to the condition of the trail. It's HORRIBLE!! Someone got the bright idea to put very large gravel down on the trail. which turned the trail into one that is only suitable for a mountain bike with suspension. Even then, it's not an easy ride. Yes, there are sections that are flat, but there are also sections that are so steep that you're forced to get off your bike to get up it. Though I'm not any sort of professional biker, I am someone who takes 70 mile road bike day trips on a regular basis. It took me five hours to go 36 miles - 18 miles out and 18 miles back. I had planned to do the entire trail out and back. If I'm having issues with a trail, there's good reason. I took my regular mountain bike (no suspension) and my body was shaken all over the place due to the trail condition. Until the trail condition is resolved, I sadly won't be returning to this trail again. It's a darn shame. On a positive note, I did see a bobcat!
* The trail description of the trail on the national park web page, the official Rails to Trails book for PA and other sources need to be updated to reflect the true condition(s) of the trail.
The bridge is repaired and the trail is open.
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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