Find the top rated walking trails in Woodstock, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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Sunny and warm July Sunday. Started from the handy parking spaces across from the Wurtsboro firehouse (corner of Pine St. and Canal St.) The informational signs in the little park back toward Sullivan St. are worth checking out before heading north on the trail.
The trail is really nice in that beginning stretch: some gravel, mown grass, hard dirt. Easy on a hybrid or mountain bike ... probably too rough for a road bike. Riding along the long-forgotten, but still totally visible, D&H canal is very pleasant. Some lengths of the canal itself are totally dry and filled with mature trees; other lengths have water. (We didn't stop to read them, but there is fun signage along the way that tells a narrative story about the area.) Mixture of shady tree coverage and open skies. Very, very nice!
BUT THEN! Big surprise. As the towpath crosses McDonald Rd and continues north, which is maybe only 1 mile from the start, the bike path is fully flooded by water and completely unpassable. This is due to a total blockage of water in the canal by a massive beaver dam. (This is right where a home, yard, and outbuildings are visible on the satellite view. And, yes, there are some scary dogs on long ropes ... that come lunging.) The beaver dam is interesting to see, but there is no way to continue on the towpath at that point.
It turns out that the Mamakating O&W rail trail also has an entrance right on McDonald Rd. We chose to ride that back to Wurtsboro. There is a supposed continuation of Mamakating that heads northeast (the satellite view shows it), and it might be possible to jump back onto the D&H trail on the other side of the beaver dam blockage. But the official listing for Mamakating shows that this length is not developed ... so we decided not to chance it.
The Mamakating trail back to Wurtsboro is a straight shot ... no problems. That unintended shorter loop was maybe 3 miles total. But worth it!!
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.
did trail 7 years ago. What a change!! Smooth all the way from Copake Falls to Wassaic!!!! Did 50 mile round trip then took a dip in the spring fed lake at Taconic Hills State park. Can walk to the lake from the trail head at copake falls. Also a nice state park with interesting sights. We stayed in Great Barrington , 10 miles from Copake Falls. Make sure you check out the Barrington Brewery. Great beer, great food.
Beautiful ride in the am was nice and cool and quiet Down hill to hopewell This time of year there are so many raspberries on the side of the trail going back to collect some for jam end of the week Being a rail trail the way back is just a slight incline Great Ride
Rough in spots but really nice ride !!! Would do it again ! Tough around the steep hill x2 , Tressel bridge !!! But nice scenery and cool breeze Pat and Kevin B
Throughly enjoyed the trail end of the trail needs some work otherwise an awesome ride !!!
Section from New Paltz (and maybe a mile or two below, I haven’t checked) to a mile or so north of the Rosendale Trestle is superb. Just after the Women’s Studio Workshop is an interesting historical furnace chimney. But then the trail comes apart - chunky gravel and hills I wouldn’t want to come down, leading to Williams Lake (saw lots of landscaping going on but no one using that end of it recreationally). I returned to the Women’s Studiovia the road.
Beautiful trail. Well maintained. Headed west from Henrietta first, a little secluded. Only went about 2 miles then headed east to lock 33. Felt safer going east. Full of exercise traffic… love to see that!
Great trail a must do . FYI bridge #1,2,3,4 were under construction but are now complete and the trail is open complete . When in Monroe just before overpass there is a good burger and place called Wayback burger . You have to pedal through a gas station lot but it’s next door .
I rode the entire 24.7 mile southern portion of the Harlem Valley Rail Trail on a beautiful fall day. The HVRT offers everything you could want from a trail experience: a fully paved surface, mostly flat, beautiful scenery (especially in the Fall) and a perfect mid-point trailhead to grab a bite to eat.
I don't recall seeing any water fountains along the trail although the trailhead in Millerton offers many options for places to eat or resupply. The HVRT offers a myriad of scenery changes from farmland, quiet streams, distant hills to quaint towns. I have ridden many paved rail trails in the past and the HVRT is one of the best with almost no surface imperfections for the entire distance. There are many trailheads along the entire trail giving many distance options. All this adds up to a perfect trail in my opinion!
Map is 6 months out of date
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