How to Have a Wilderness Cycling Adventure in New York City
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If you follow cycling influencers or regularly read outdoor-themed lifestyle publications, you may assume that you’re the only person who’s not biking on gravel roads or disappearing into the wilderness on exotic bicycles laden with high-tech baggage systems. Quite the contrary: schlubs like us who are stuck in urban areas account for 80 percent of the population of the United States. Moreover, only half of us can afford a summer vacation, which means if we want to maintain both our riding lives and our sanity we’ve got to make do with whatever we can find in our backyards.

I live in New York City. While the nation’s largest metropolis is known for a large bike share system and chronically obstructed bike lanes, few people equate us with a recreational cycling paradise. Yes, it is true that four out of the five densely-packed New York City boroughs are situated on islands, meaning getting out of the city for a ride can be a frustrating experience akin to punching your way out of a cardboard refrigerator box.

However, I’m fortunate to live in the Bronx, which is the only borough connected to the mainland United States. This means it’s easy for me to slip out the city’s back door and onto roads and trails that give the facade of riding in the country.

Ironically, it’s precisely because the city is such a massive and ever-growing metropolis that it is so easy for me to get out of it. There are two car-free trails that transport me directly from my home to some of the area’s best riding, and both are built upon the city’s sprawling infrastructure.

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One of these is the Empire State Trail, a paved bicycle path that sits atop a former commuter rail line, and the other is the unpaved Old Croton Aqueduct Trail, 26 miles of dirt along the city’s 19th century drinking water. Both these trails head straight north into the “country,” which not only makes escaping the city by bicycle ease, but also makes the decision between riding road and dirt as easy as flipping a coin.

On one recent particular outing, I decided to ride road and dirt, so I headed into the park and onto the Empire State Trail, where in a matter of minutes I arrived at the New York City line:

ride report adventure in your back yard
This bike path leads riders in and out of the Bronx (Photo: Eben Weiss)

As you can see, the pavement markings that tell everyone where to go abruptly end when you leave the city, which is how you know you’re really in the wilderness.

Being an old train line, the Empire State Trail boasts loads of features which delight both the rail nerd and the history buff, including ghost stations and a Civil War memorial.

ride report backyard adventure
A ghost station along the Empire State Trail. (Photo: Eben Weiss)

Gone are the rail cars (service on this railway ended in 1958), and in their stead you’ll find cyclists pedaling off into deepest suburbia. As for me, having traveled about eight paved miles since crossing the city line, I figured it was time to put my fat tires on some dirt.

There are a number of popular mountain biking spots close to New York City where on any given weekend you’ll find parking lots full of SUVs and riders prepping their dual-suspension bikes for an hour or two of riding over the same obstacle repeatedly. For years, I too drove places to go mountain biking, but over time I lost my taste for it. Why spend time driving when you could be riding?

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The Empire State Trail is popular with cyclists in greater New York City (Photo: Eben Weiss)

Furthermore, while riding to these destinations, I’ve discovered all sorts of little spots I’d otherwise have missed had I loaded my bike into the car. When you’re driving you’re focused on the road (well, ideally, anyway—most people seem more focussed on their phones or whatever they’re vaping) but when you’re riding you spot little gaps in the trees, notice little trails beyond them, and ask yourself, “Where does that go?”

Sure, sometimes you follow it and find out it just goes to some nasty spot strewn with detritus where someone’s been sleeping for six years, but other times you find a whole new set of trails you never knew existed, like that recurring dream where you discover another wing in your apartment. These are the places nobody drives to, because they don’t have parking lots, and they can be some of the very best places to ride.

On this particular occasion I was headed to a spot I discovered many years back when I was riding in light snow. In the distance I spotted a rider on a fat bike, and while he was too far away to catch I managed to follow his tracks. These let me to a trail I always figured just led into someone’s backyard or something, and I’ve been coming back to the area and finding new stuff ever since. No parking lot, no trailhead, just a little gap in the guardrail.

Sometimes the best adventures start with a gap in the guardrail (Photo: Eben Weiss)

It may not be exotic, but when you ride to the ride everything feels like a little bit of an adventure.

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Plus, few of us have the time for actual adventures—much less time to get lost. There are places where the price of exploration is finding yourself deep in the wilderness as the sun sets and having to build a shelter and spend the night. That’s not really compatible with my lifestyle, and I much prefer the sort of exploration where the consequences of a wrong turn are winding up in the parking lot of a Chipotle—which if you think about it is less of a “wrong turn” and more of a happy accident.

Sure, the closer you are to civilization the more rules there are. For example, when you stop to rest beside an inviting body of water on a hot summer day it’s usually surrounded by signs admonishing you not to swim.

If a tree falls in the forest and there’s nobody around to hear it does it make a sound? I have no idea. But if a sign in the forest tells me not to swim and there’s nobody around to see me then I’m going in anyway.

No modern cycling adventure would be complete without a dip in a lake, river, or pond (Photo: Eben Weiss)

There are all sorts of tricks you can play to make a short ride feel like an adventure. One of them is an illicit swim, and another is avoiding paved roads as much as possible. So, for the return trip I hopped on the Old Croton Aqueduct Trail. If you know where you’re going you can pretty much ride dirt the whole way back to the Bronx. Just keep the Hudson on your right shoulder.

You’ll barely encounter any cars, either, though you do have to watch out for the wildlife:

deer
Watch out for the local fauna! (Photo: Eben Weiss)

I wonder if that deer has deluded itself that it’s living in the wilderness as successfully as I have.

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