New York & Connecticut’s Top Rock Climbing Destinations (Within Two Hours Of Westchester)

It’s high time to start your rock climbing adventures and join the hoards picking up the sport.

It’s hard not to be impressed watching Isabella Boxer scale an enormous cliff deep in the woods of Plainville, Connecticut. But the fearless 10-year-old Larchmont resident says, “You know that if you fall, you’re just going to hang there.”

Okay, so maybe most people can’t so easily brush off the fear of falling. If Boxer and her intrepid fellow campers from The Rock Club in New Rochelle can climb without hesitation on a day trip to Pinnacle Rock, shouldn’t you at least consider trying it?

Rock-climbing filmmaker Josh Lowell—who, along with his brother Brett founded Pound Ridge-based Big UP Productions and has been making climbing films since 1997, even winning a Sports Emmy for his work—says there’s been an uptick in people taking up the sport. “A decade ago, when I would tell somebody I was a climber, the only thing they knew in reference to climbing was Mount Everest,” says Lowell. “That’s changed because everybody’s kid has gone to a birthday party at a climbing gym.” Aside from indoor gyms, Lowell attributes the increased exposure to and interest in the sport to climbing media, like compelling YouTube videos of climbing.

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Climbing is also emerging as a strong alternative to traditional team sports, says 14-year-old Pelham resident Jake Beckman, who climbed Pinnacle Rock during the Rock Out! summer camp run by The Rock Club. “It involves a lot of stuff that you wouldn’t get with a ball sport,” says Beckman. “You can test yourself as opposed to your skill with a ball. You’re channeling yourself into the rock.” 

As part of a summer outing, members of The Rock Club climb a boulder in Plainville, Connecticut. 

While much of the buzz about rock climbing in the county stems from the increasing popularity of indoor gyms, if you’ve mastered the controlled environment—or if you’re new to the climbing world—and want to step outdoors, here’s how to get started. 

How to learn

“The most common way is mentorships,” says The Rock Club guide Maya Obstfeld. “You just find someone—one of your friends, maybe—who’s a much better climber with experience, and latch on.”

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But if your friends are more the Netflix binge-watching type, your best bet would be to link up with one of Westchester’s prominent indoor gyms—The Cliffs at Valhalla or The Rock Club in New Rochelle. You can train on indoor equipment to learn the basics, and eventually make your way outdoors with a mentor or through gym-sponsored programs. 

Where to climb

Though there are spots in Armonk and Pound Ridge where people climb without permission, Westchester itself is thin on sanctioned spots for outdoor climbing. We checked with Mary Kaye Koch, director of marketing for Westchester County Parks, Recreation and  Conservation, and she told us that the county’s parks don’t offer outdoor climbing, and there’s currently no discussion about adding it. 

Luckily, there are plenty of locations within a two-hour drive of Westchester, including the Shawangunk Mountains (known as The Gunks), the Metacomet Ridge in Connecticut, Powerlines in Rockland County’s Harriman State Park, and Minnewaska State Park Reserve near New Paltz, New York.  

“People who live here are very fortunate to have close access to incredible places like the Shawangunks and the Connecticut climbing areas,” says Lowell. “While nobody is moving here to become a climber, if you’re interested in learning, you’re in a pretty good spot.” 

Of the nearby destinations, The Gunks (an hour-and-a-half drive up the New York State Thruway to exit 18 in New Paltz) isn’t just the most hallowed, it also offers the most options—even for novices looking to break into the sport. A $10 day pass purchased at Mohonk Preserve’s Visitor’s Center gives you access to a world-class climbing site, with more than 1,000 or so climbing routes, the majority of which fall in the easy to moderate range, and more than five linear miles of cliff face. (Most routes are rated 5.3 to 5.9 on the rating scale ranging from 5.0 to 5.15; the higher the number, the more difficult the route.) The average route is 150 feet high, with the maximum soaring 300 feet above the tree-covered landscape that stretches all the way to the Hudson River. “It’s a privilege to be able to climb in these beautiful, natural spots,” says Lowell.

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Act the part

Just as all sports have cultural etiquette—how dare you mention that perfect game in baseball—there’s a proper way to act when climbing outdoors: Keep a low-profile; don’t yell (it’s a safety concern); minimize your impact on vegetation; and pick up your trash. 

“If people are a little more gung-ho, they’ll just buy their gear and go out,” says The Rock Club Guide Matt Raue. “But they’re also coming with their dogs and their boom-boxes, sticking gum on trees. There’s a lot to learn about the transition outdoors.” 

The campers Raue brought to Pinnacle Rock got a first-hand lesson in what can happen when climbers don’t consciously minimize their impact. While some cliffs are monitored by preservation groups that clean and occasionally close portions of them to allow for ecological regeneration, this space is not. Shattered glass littered parts of the cliffs, and a climber from a nearby party howled in pain after reaching for a ledge and clamping down on a fist full of glass. 

Hence the code of care: “The rock is limited,” says Raue. “There’s no more rock shooting out of the ground.”    

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