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Sunday’s trail run was a long time in the making. I’d been somewhat obsessed with the very idea of trail running since reading Born to Run, but knowing that the concrete jungle doesn’t afford many opportunities for soft surfaces (save for the reservoir and a collective 20 feet on the East River), I gave up the thought pretty quickly.

I’ve been blazing the pathways of Manhattan for quite some time now though—from east to west, north to south. You’re more likely to find me trekking along the lower loop of Central Park on any weekday morning than under the covers of my blanket. Saturday morning? That’s reserved for Soho or the reservoir. And of course, there have been many fun runs in between, spanning the Queensboro Bridge…

…to the East River…

…to the West Side Highway and more. The farther I run, it seems, the more expansive my stomping grounds become.

More recently, however, I’ve been unable to shake my trail running urge, and so last week, Noah and I planned an outing in Cold Spring Harbor, Long Island. Naturally, the night before, I woke up in a sweaty pool of fever grossness, and was unable to follow through with the day I had been waiting to come for so long.

Fortunately, I’d only have to wait a week before our second attempt at trail running. Spending Sunday – Mother’s Day – on Long Island gave us the perfect excuse to try again; we were getting a ride on the early side anyway and would be able to head out to Cold Spring Harbor with relative ease.

Finding the entrance to the state park was simple, and if you live on or near Long Island and have never hiked the Greenbelt Trail, then I highly suggest you do – even if only walking it. The vertical climbs alone are certainly tough enough to break a sweat.

By car, all we had to do was take Northern Boulevard (25A) out about 35 minutes east of Great Neck. There’s ample parking for the trail on the right, across the water, just past the Cold Spring Harbor library, and you can pick up the pathway there.

Everything was set for Noah and I to spend a perfect hour or so spent grunting our way through the woods, and yet I couldn’t help but wish that, prior to lacing up my sneakers, I was just a bit better equipped for what was to come. Call me naïve, but while I know that trail running is a whole different beast than even the biggest of Manhattan’s hills, until you’ve tried it, it can be really difficult to anticipate what’s to come.

New to trail running too? Let me make your life easier with the 5 facts I’d wish I’d known beforehand.

1. Save your energy. I know. It can be really, really exciting as you take those first few steps into the woods—especially if you’re coming from a jungle of urban sorts. But racing up the mountain was probably one of the biggest (and most rookie) mistakes I made on Sunday morning. Rather than working up my endurance and saving my strength, I exploded like a horse out of the gate and wound up spending the rest of the run trying to catch my breath.

2. Beware of living creatures. Snakes, to be exact. In case you didn’t know this about me (I’ve mentioned it once or twice), I have a huge fear of thunder, dark, deep water and snakes.

Fear numbers one and two really had no bearing on me on Sunday. And because I spent six summers at sleep-away camp and have a house in a wooded area in Connecticut, I know that fear number three is harmless more often than not. That doesn’t mean I won’t pee my pants a little at the sight of one though—even if it’s small.

Yes, while I was in the lead, Noah trailing behind me (otherwise he’d have raced past me in a literal cloud of dust; I set the pace when we were on relatively flat grounds), I spotted a tiny snake off to the side of the trail. To my benefit, because I was already running, I was already prepared to sprint away while screaming OMG snake. Noah obviously stopped to check it out, and proceeded to ogle this evil creature with another hiker who was passing by. Fools.

3. Pee first. I find this one unfair, because I actually did pee before leaving the house. Perhaps this tip should read, “Don’t drink an entire medium iced coffee from Dunkin’ Donuts,” but I did, and by the time we pulled into the parking lot in Cold Spring Harbor, I had to relieve myself again.

Naturally, there was no bathroom in sight—just a giant body of water to mock me in my pain. I figured the sensation might pass once we started running, and it did for a little while. About 1.5 miles in though, I really had to go. I stopped several times to attempt to squat behind a tree, but then I’d spot a family hiking in the distance and get shy. It pretty much took total desperation and the threat of actually wetting myself to finally stop and mark my territory. This is now my tree, in doggy terms.

4. Leave your ego in the parking lot. That may have been one of the more frustrating aspects of the morning. I suppose I envisioned myself gracefully galloping through the woods like a gazelle or something; instead it was more like a 5-mile asthma attack, and even flat surfaces made me wince by the end.

In truth, there were many inclines that I couldn’t even make my way up all the way to the top without walking, or even stopping completely in the middle to catch my breath. Noah said it was probably a combination of being unfamiliar with the type of conditioning needed for trail running as well as my lingering cough and sore throat. He’s probably right too. But still, I’ve never walked during a run, and I wasn’t planning to start on Sunday.

That said, trail running is very different than, well, non-trail running. I knew this going into it; I just didn’t quite internalize what that meant. Now, I have a new obsession: conditioning my body to the point that I’m a trail running beast.

5. Safety first. Seriously. The course we took could basically be broken down into three segments, the first and, what would presumably be the last, being by far the hardest and hilliest. As mentioned before, I exhausted myself almost right off the bat, and so a lot of the run was spent catching my breath and doing my best to stabilize my heartbeat as I pushed on through the woods.

The first time Noah suggested that we follow the road back for the last third of a mile of the course, we were exactly at our halfway point. I scoffed. I had already broken cardinal rule number one by walking during our run. (Granted, some parts were just too steep, and given my conditioning – or lack thereof – I didn’t have much of a choice. I was hitting wall after wall after wall.)

Skipping the last segment in order to – literally – take the easy road was out of the question. The second and third segments weren’t so bad anyway, and so as we backtracked toward the scary hills that defined those first 20 minutes of the run, I was feeling generally okay.

Had Noah not been with me on Sunday, I’d have unquestionably sucked it up and finished that final segment of the trail. I’m just stubborn and reckless like that. I also might have twisted an ankle, broken my pelvis or at least scraped my knee. He could see it in me; me legs were tired, I wasn’t picking up my feet like I should be. One misstep and I was a goner, or at least, I’d risk potentially injuring myself.

So I conceded. Noah and I jogged along the road to get back to the car, skipping over that final, arduous incline to top off our 5 mile run. Looking back, I’m definitely grateful that I had his wise words echoing in my head.

So there you have it. Sunday’s highly anticipated trail run was a major success, even if it had its – wait for it – ups and downs and was wildly challenging.

Don’t get me wrong; I love running in Manhattan. But even the best running routes can become monotonous after, say, 500 or so times. And although I plan on milking the summer for all it’s worth by waking up super early and hitting the scorching pavement as much as I can from now through fall, I’m also equally excited to keep checking out different trails periodically. If nothing else, it’s a great way to keep my body guessing and improve my conditioning—and the perfect excuse to escape the city heat.

  • Have you ever gone trail running and experienced any of the above?
  • Did I miss anything? What could I add?
  • Does snake repeller exist?