Orange to Ulster

For this author, a big part of the joy of bike trips is figuring out how to make an itinerary work in the first place. Not all trails connect and you’ll have to put time on the road. Wayfinding isn’t always obvious. Terrain is varied, more often than not erring on the side of bumpy. Sometimes you find yourself in the sticks delayed with a flat tire. &$!#%... Eventually it works out, and you feel grand. Journey not the destination, right? 

Orange to Ulster is that journey, at day-trip scale. Master this one and you’ll easily muster the confidence to take on lengthier bike trips further afield. 

Harriman >> Poughkeepsie via Goshen and New Paltz

Getting there and away. Starts with getting to Hoboken Station first. That’s right, Metro-North’s Port Jervis Line departs from Jersey. You can get there easily on the Path train or the NY Waterway ferry. Note, you’ll be returning on the Hudson Line into Grand Central.  

Safety first on the roads. Right out the gate at Harriman you’ve got a little over a mile and half (~10 minutes) on-road before you hit Heritage Trail. No big deal, BUT… half of that time is on Route 17, which is four lanes of fast traffic and not much of a shoulder. It’s not fun, you won’t like it. Fortunately, that bit is a very short jaunt. At the end of the Heritage Trail, you’ll have another 15 miles (~85 minutes) of on-road time between Goshen and Walden. Here are some pro tips for on-road riding if this is new territory for you: 

• Pro tip #1: Get a good rear bike light. No, not one of those weenie blinkers you use for your city commute. Bigger, brighter, better—something like this one.  
• Pro tip #2: Take the lane. Better the cars honk, at least then you know they see you, than scream around the corner only to suddenly find you hugging a barely-there shoulder. 
• Pro tip #3: Ride in pairs. Two bikes in the lane are more visible than one. You’ll see motorcycles do this all the time, it works.  
• Pro tip #4: Ride early. I generally try to time any lengthy on-road time to early AM on bike trips. Country roads are generally pretty quiet before 10am, especially on the weekend. 

Google Maps is your friend. There is a whole world of bike computers that use GPS coordinates to get you from A to B. There’s also a Ride with GPS app that replicates the same functionality on your smartphone. I’m sure those things are all great. I started simply with Google Maps, however, and have stuck with it ever since. Rather than put the ultimate destination, I’ll save a bunch of intermediary stops and then map directions point-to-point. This helps me stay on the slower quieter roads, rather than the most direct ones.

Sorry, no foodie recs. I did this trip several years ago and don’t remember eating anything memorable along the way until we woofed down burgers and beers in New Paltz (Clemson Bros. Brewery). You’ll ride through plenty of towns—Harriman, Monroe, Chester, Goshen, Walden, Wallkill, Gardiner, and ultimately New Paltz—so no shortage of options.

Despite everything above, this is actually a really fun trip! You’ll ride through a pretty corner of New York that’s a good bit more rural, grittier, and less polished than the river towns and Catskills getaways that get all the New York Times write-ups. And you’ll feel grand when you complete it because it is a bit of a challenge! You can also add to it. Make it a weekend trip with the Kingston Weekender or Shawangunk Screamer, or make it part of a bigger multi-day tour with the Mid-Hudson Tour.

Trails

• Heritage Trail
• Walden-Wallkill Rail Trail
• Wallkill Valley Rail Trail
• Hudson Valley Rail Trail
• Walkway Over The Hudson