Find the top rated walking trails in Windham, 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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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Map is 6 months out of date
Trail is all gravel so be careful ! It starts in the center of town in New Paltz goes into a field of green & a view of a mountain it’s ok but I would not do again .
Went from the Thuway area in Poughkeepsie over the walkway and ride to Hopewell junction .Nice trail well groomed , paved not much to look at but very cool what the volunteers did to the RR depot , signal house and pavilion, the depot museum was great . Went to Daddy O’s restaurant on the trail , good food . The NY empire trail continues along live tracks goes I believe quite far .
Nice trail a must do . From Kingston it’s paved at least 5 -6 miles the rest is easy ride great scenery !
Wildly inconsistent and discontinuous trail. Has potential, but I sense it will be many, many years before this will rival the trails on the east side of the Catskills. Skip this and just go to the Heritage Trail in Middletown.
Nice and wide. Plenty of room for walkers, runners and bikers alike. Hudson Valley really has a great series of trails and this is one of them. Connects the Walkway Over the Hudson to the Maybrook Trailway. Bikers dream.
This trail (14 mile section) was in pristine condition with surprising amount of wildlife (herons, deer, turtles) along the way. Park, falls and 1800's mill factory at the southern end was worth a stop. Maybe shaded 50% so suntan lotion a must. There's a parking lot in Nassau right next to the trail. As others have mentioned, very few bathroom facilities on route.
I tried this trail starting in two spots. First at the north end off 208. The first few hundred yards are good, but then it becomes overgrown. I went through the brush and mud for another few hundred yards, but turned around at a washed out culvert. Next I drove to the north end of the southern section off S road. This was better. Bumpy with roots across the trail. Foot tall grass in most places, but passable for a half mile or so. After the underpass there are several bridges in degrading condition. I didn't dare ride across, but walked these. There were also downed trees in two spots. A little over a mile in I turned around at another rotting bridge that had 3 large snakes (I believe Northern Water Snakes, but not 100% sure).
I wouldn't waste your time with trying this trail.
This mostly flat, well maintained trail goes though woods and across dykes. The scenery makes this a near perfect trail.
Wassaic to Orphan farm and back will take you through farmlands, marshes a bird sanctuary and a long bridge over the marsh that you must just stop and absorb the place.
A great place to train because you draw strength from the scenery and there is lots of shade and lots of benches along the way.
Have respect for others that are smaller (tricycles or training wheels) and older folk sharing the trail and you will have an outstanding ride / walk / run.
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