With Community Series Trailish, New York City Runners Go Off Road

Now I'll admit, I am not the most enthusiastic runner in the world—I prefer to do my cardio on a bike whenever possible—but I have managed to experience so-called runner’s high on a few occasions. I felt it the first time I tried to hang on with the faster folks in my after-dark run club (shout out to the Nightcrawlers) and when I sprinted to finish the New York City marathon last year. I’ve always believed trail running could provide the feeling with less effort, and make moving your feet one in front of the other feel more like play than exercise. Yet I live in fear of twisting my ankle on an unseen root.

Could Trailish provide a welcoming space for me to give it a real crack? Here, we’ll dive into how it fits in the context of trail running programming within the city, what your event ticket gets you, as well as what I, a person who has now attended one of the runs, would recommend you make sure to bring if you decide to go.

Trail Running in New York City

New York is a concrete jungle, but there are more places to try trail running than you might expect (same goes for surfing and rock climbing). Each borough boasts at least one park with tree-lined, dirt and gravel paths that allow you to get your feet muddy as you attack hills and navigate obstacles underfoot. In Manhattan, the North Woods of Central Park are a nice introduction. Just make sure to be polite to the birdwatchers. In Brooklyn, Prospect Park is full of trails that run parallel to and criss-cross through the main loop. The eastern section of Forest Park in Queens hides some stunning trails between the bustle of Jackie Robinson Parkway and Myrtle Ave. Similarly, Van Cortland park in the Bronx squeezes a ton of fun trails in a relatively small area.

The haven for trail running within New York City, however, is the oft-overlooked Staten Island. Clove Lakes Park offers a marked path that switches between paved road and off-road surfaces with a decent bit of elevation game, ideal for beginners. More intermediate runners should head to the Greenbelt, a system of parks smack dab in the center of the island and New York City’s largest remaining forest preserve, that features over 35-miles of rugged trails to try.

Tried all those and want more? There’s tons of trails just outside the city, both in north New Jersey and the Hudson Valley. Just off the Metro North train, you can get to the Rockefeller State Preserve, Breakneck Ridge, and Bull Hill. And if you’re willing to cross over into New Jersey, you should try South Mountain Reservation, mere steps away from the Millburn NJ Transit Station.

Trail Running Clubs in New York

Despite this abundant dirt surface, there are very few active trail running clubs in New York. The Brooklyn Trail Club, a subgroup of the Brooklyn Track Club, and Asian Trail Mix—a community that aims to make trail running more accessible for all people of color, but particularly Asian American and Pacific Islander individuals—both host regular open-to-the community trail runs at different spots around the city that are accessible via public transportation.

Occasionally, some running brands will also host trail runs. The most dedicated I’m aware of is Miler Running, which amazingly produces all of its gear within New York City. After launching a collection specifically targeted towards trail runners last summer, founder Ben Morrow planned a “Sunrise Series” of runs in a bunch of different Brooklyn parks. He just told me he’s planning to start up the series later this spring, so keep the brand on your radar.

Trailish Group Run Events: What to Know

Trailish is a welcome step to closing this gap. Regular trail runs are something Outlandish founders Ken Bernard and Benje Williams, himself an impressive trail runner, have wanted to add to their event programming since they opened the store in 2023. The partnership with Hoka, which is providing two different demo shoe options for runners, helps make sure that the event would be accessible for newcomers without having to buy new gear.

The ticket price for each Trailish run is $50, which mostly goes to cover the cost of passenger vans the Outlandish team rents to transport runners to and from the trail head. Our event had an extremely reasonable meeting time of 9 am, with a planned departure scheduled at 9:30 am. That gave me plenty of time to get fitted for a pair of demo shoes (I went with the new Hoka Speedgoat 6s), meet some of the other runners, and take on some much needed fluids. (Read: down two cups of coffee.)

Before a quick ice breaker, Ken took some time to introduce the runners who would be equipped with walkie-talkies and first-aid supplies, in case of emergency. Then, we boarded the buses and headed to South Mountain Reservation. The trip only took about 45 minutes, but I’ve but I’ve been told some of the future trips will be to further away locales.

When we reached the trail, Inma was waiting for us, having spent the last hour and a half scouting the route to make sure our plan would not have to change too much due to the rain. We did some dynamic stretches as a group, then listened while Inma prompted us for some muddy conditions, tree fallings, and the aforementioned river crossing, but also encouraged us to take the day at our own pace.

Indeed, I can say with confidence that Trailish is not a race. For the first half of the run, I found myself alternating between a gentle jog and an ambling walk, as we made our way single-file through the narrow path parallel to the creek. When we reached the crossing, I had hardly broken a sweat. I felt confident I could easily clear the creek with a hop. Alas, I misjudged the fidelity of my destination—the pile of leaves was actually just a cover for more creek.

Though my right foot was now thoroughly soaked, I pressed on with the rest of the group, about 34 people in total. I learned that some were experienced trail runners with several ultramarathons under their belts, but others were trail running for the first time. It felt like an easy space to commiserate about wet socks, solicit tips about proper technique, and fantasize about eating lunch on the other end.

After we got to our end destination, a lovely waterfall, we were each given the option to either come back the way we came, or go down a wider and less technical gravel trail. Feeling ready to open it up a bit, I chose the latter and enjoyed attacking the rolling hills with as much gusto I had left to muster. As I made it to the finish, I couldn’t help but smile. Not only had I not broken anything, but I had genuinely enjoyed myself. Maybe this running thing isn’t so bad after all.

Trailish 2025 Schedule

There’s one Trailish run currently planned on a Sunday during each month through the rest of the year. You can sign up for the upcoming one via Outlandish’s website, where you’ll also find updated information about possible changes to this schedule.

• May 11 - Mother Nature Trailish, Delaware Water Gap
• June 8 - Pride Month Trailish, Minnewaska State Park
• July 6 - Independence Day Trailish, Fahnestock State Park
• August 10 - Hot August Trailish, Mullet & Denton Falls, NY
• September 14 - Summer Finale Trailish, Ramapo Valley Reservation
• October 12 - Peak Foliage Trailish, Teatown Lake Reservation
• November 9 - Gone till November Trailish, Hudson Highlands State Park
• December 7 - Fall Finale Trailish, Storm King Mountain

What to Pack for Trailish

Though the Outlandish team was extremely communicative before the run about what runners might find helpful to have with them on event day, I still left my house without a few things I could have used. Here, what I think you should bring.

• Extra socks: A trail might be muddy and wet even if it isn’t currently raining. This is probably obvious to any expert hiker or trail running, but I simply didn’t prepare to end my run with soaked socks. If I was traveling back to Brooklyn in a car by myself, I’d have no shame in taking off the offending socks and just hanging out barefoot until I made it home. But you can’t do that in a passenger van without making enemies. So just bring extra socks.
• Extra layers and a change of clothes: It was cold when we arrived to the, which made the minutes before our warm-up and run a bit uncomfortable. People who brought a warm up jacket and pants, as well as a sweatshirt they could don after their run, were the most comfortable. In the summer, you’ll still want a change of clothes for the opposite reason—it would be super unpleasant to sit in your sweat for hours.
• Water: The Outlandish team bailed me out with some Poland Spring plastic water bottles, but I really should have brought water to drink before and after the run. The run wasn’t so long or intense that I felt I needed a vest that would have allowed me to drink during my run, but I felt bad drinking out of a disposable plastic water bottle as I waited for others to finish their run.
• Lunch: Before everyone got back in the vans to return home, we took about a half hour to sit at the picnic tables. When all my fellow runners started to pull prepared sandwiches wrapped in foil and grain bowls packed in Glasslock containers out of their backpacks, I knew I had made a mistake. Luckily, I had brought some Clif bars as potential fuel for my run (yes yes, not optimal, but it’s what I had!) that sustained me through the journey home, but I would have been so much happier with a real meal. Thankfully, someone brought a can of Pringles they were willing to share. It’s not the first time (or the last) that I’ll be bailed out by another New Yorker.