Bicycle Touring NYC to Wookstock, NY Via Metro North

A little over 80 miles North of New York City is Poughkeepsie, NY, a connection to the Hudson and Wallkill Valley Rail Trail, and finally the Onteora Trail which will lead you in route to Woodstock, NY. This is intended to be a bicycle touring gravel route that is capable of accomplishing on-road or fat bike style rigs. It can be a full day or an overnight adventure packed with nuances and scenic views every mile. For us, it was a quick weekend getaway that’s mixed with 80% dirt and gravel. I’ve ridden this route solo couple of years ago on 23mm race bike tires on my full carbon road bike set up for a fast light tour.

This trip was a duo with my friend George and I. He’s a skilled mountain biker at heart with the desire to travel by bike. This was also the first trip I’ve gone on with George, and certainly not my last as we had plans to do future trips together that were extended overseas travel. You can sense the companionship through banter, views of the world, and geeking out over bike stuff. I knew it was going to be a great trip.

The route is mainly intended for travel by rail via Metro North from Grand Central Station in New York City. Once aboard the train to Poughkeepsie, you’ll be relaxed for two hours. George and I conversed back and forth and before we knew it, we were on our bikes and off to the “Walk Over The Hudson”. This will put you directly on Hudson Valley Rail Trail. This 4-mile gravel trail passes through wood forest and creeks before leading you through New Paltz, NY where you will then pick up the Wallkill Valley Rail Trail.

The end of this trail will put you on NY-375 in Woodstock, NY and from here you’ll be making just a few more turns down quaint country roads before ending in the center of town.

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I recommend stopping at Overlook Mountain Bikeshop. The guys there are cool and can shed some light on the area if you’re new in town. You have options to stay in a hotel in town or camp in the mountains. If you decide to camp, Rock City Rd will lead you into a climb with a big grade leading to the base of a trailhead. Depending on your weapon of choice you can ride up the mountain to camp at either Echo Lake or Overlook. I had to hike-a-bike up. The views are well worth it.


I hope this article provides value for you. If you have questions about bicycle touring and bikepacking contact me for a personal 1 & 1 consultation and I can offer you value on getting you started from selecting the right bike and equipment. 

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Ridden & Written by

Dwayne Burgess / Manual Pedal

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