Wintergram Wonderland: Everything You Ever Wanted to Know about Winter Hiking & Photographing in the Hudson Valley

  |  February 28, 2020

Photo by Matthew Chase of @Upstateface 

Running the @Upstater account, I’ve become increasingly familiar with both the media and local landscape. An upstate weekend getaway usually conjures up images of lake house relaxation, Woodstock festival vibes, summertime swimming holes, or mountains ablaze in peak leaf season. In searching for aesthetically pleasing outdoor images to share, I assumed good photo options would drop off along with the temperature But I was surprised to find that many of the most dynamic and breathtaking images posted each year are taken after a heavy snowfall.

Photography tip: For best composition shoot during low light hours of dawn or dusk

As my only experience with winter hiking was a failed attempt at Huckleberry Point, I began to delve into the wonderland that is Upstate New York outdoor accounts for winter content. It was like rediscovering some of my favorite destinations for the first time. In talking to the people behind the profiles, I hoped to glean some insight on the singularity of hiking the Hudson Valley in the winter and how to make it off the mountain safely as well as respectfully ‘gram afterwards.

“Never Too Cold for a Winter Hike”

My first question was, is it really worth it to break out the hiking boots on the coldest days of the year? Sean O’Dwyer of @Totalcatskills doesn’t sugarcoat it. “It’s just so extreme,” he says. “There’s the three seasons and then there’s winter. It’s very challenging but super fun and so beautiful. Not just the scenic vistas, looking across snow-blasted mountains and valleys, even just walking through the woods on a sunny day after a fresh snowfall, it’s just mind-alteringly beautiful. We all use the phrase ‘winter wonderland’ because it is truly that magical.”

Photography tip: Take a lot of photos so you have options later and try different heights and angles—sometimes a small shift makes all the difference. 

Rockland County native, Stephen Tannberg (@Nynjhiker), who has hiked 48 of 48 Harriman State Park trails and 18 of the 35 of Catskill high peaks, agrees that winter hiking is thoroughly underrated. “I personally feel that hiking is more enjoyable in the winter. You can see more of the landscape when the leaves are down,” he says. “You also don’t have to deal with the heat, humidity, and bugs, which is definitely a plus. And while it can certainly be too hot for a summer hike, it can never be too cold for a winter hike as long as you are wearing the right clothing!”

The Hudson Valley in particular offers a variety of dynamic landscapes especially heightened by the winter conditions that provides a unique position for Upstate hikers. “I can’t think of many places that have such easy access to lighthouses, mountains, rivers, waterfalls, swimming holes, gorgeous untouched woodland, and homes that were built around the birth of our nation, says Christopher Henshaw (@Mr.henshaw). “It’s a nature photographer’s dream!”

Tip: Set hiking goals instead of Instagram goals. Great photos are the added bonus.

Hiking Safety

All these hiker-photographers touched on the very thing that had most struck me—the aura of peacefulness that seemed to be radiating from these photos. But while these Instagrammers make it look easy, none of them claim to be trained hiking guides or professional ice climbers. Rather, I realized, people like Matthew Chase, who runs @Upstateface, and Dwyer started hiking fairly recently. Chase began got his start with another popular Upstate Instagrammer @Ianpoley before setting out on his own and O’Dwyer began by following relevant hashtags like #Catskill3500 and #VisitCatskills and then seeking out the sites.

Photography tip: Watch the weather! Research what cloud cover leads to what type of photo. 

Knowing this, I began to message these Instagrammers and ask how a fair-weather hiker might get into winter hiking photography. They were more than happy to weigh in. Clay Banks (@Clay.banks) explained how to safely find the picture-perfect hike: “I have a number of favorite locations bookmarked that I keep tabs on during the snowy season. I also check Instagram locations for recent posts in areas I’m interested in, this is helpful in gauging how accessible an area is.”

Banks, who hikes all over the world, suggests the @alltrails mobile app before doing a winter hike due to the trails reviews from other experienced hikers who offer invaluable insight to trail conditions, directions, weather, road closings, and more. “I owe it to All Trails, 300 percent, for my returning safe and sound from an unexplored and potentially dangerous hike,” says Banks. “Also get a pair of crampons. They will save your ass one day.”

Photography tip: on a classic view, look for new angles

“It’s definitely a hard time of the year, but I make it work,” says fellow photographer Dante Digio (@Dantedigio). “I always prep my gear for the worst of conditions. In the wintertime, layers are a big thing, and if you’re out hiking then ice spikes are a key component when it comes to traveling safe.”

Most of the Instagrammers couldn’t speak highly enough about how enriching this hobby is, and with proper precautions, how absolutely worth it it is. “It’s opened up my world. It’s made my life richer,”  O’Dwyer says. “Sharing photos online is a way to relive all that experience and to connect with people who feel the same way.” It’s like a Brave New Catskill Hiking World.


Despite excitement about the new trend, there’s a heated argument that comes up often in the Catskills and the comment section. Namely, the harm that social media can do to previously pristine locations. Most locals have seen firsthand the damage that excess traffic and carelessness can cause to a trail or swimming hole. It’s important to ask if pointing people in the direction of a “peaceful” winter hike will be its very undoing? And, is it a safety concern to make difficult winter hikes with treacherous terrain look easily accessible?

A really mindful take came from O’Dwyer who said, “thoughtful hikers follow Leave No Trace principles, and this extends to social media posts.” He explains that while outdoor Instagram pages succeed by offering the viewer the possibility of accessing special spots and scenic views, popular accounts really have to be careful geotagging certain locations. “You will definitely drive people to locations, and many of them may not be prepared. There are rescues all year round in the Catskills.” He suggests driving people to less popular but extremely rewarding places, to relieve the stress on the more popular spots.

Photography tip: Instagram crops at a 4:5 aspect ratio, so consider where the subject is positioned when composing the shot. Also IG loves cats and dogs! 

Henshaw also spoke of his own negative experiences. “The amount of times I’ve had to clean up other people’s trash is mind boggling, and for that reason I only tag locations that are public state parks,” he says. “For me, it’s all about awareness. I want people to see how beautiful our local wilderness is, and through that awareness, respect it.” Chase also voiced some sadness at “secret” Shawangunk spots from his childhood being popularized due to social media but called the phenomenon “inevitable,” saying that at this point “showing the region through pictures can really enlighten people, especially from out of state, as to the amazing landscape New York has to offer.”

Digital Community

The more I got into it, the more it seemed that most of these accounts are not focused solely on the social media clout but actually forming a community out of a love of enjoying the outdoors. For example, I was impressed to find out how many of these viral accounts primarily used smartphone photography. Many of the hikers said while they bring DSLR cameras, it’s always good to have an iPhone since winter hiking is more about, “BEING THERE” in the moment, as Ian McCartney of @Hudsonvalleyhikes says. In other words: hiking first, pictures second.

Photography tip: Use recent, local nature/hiking books to find lesser known hikes and secret gems

While the overcrowding of a small area almost too beautiful for its own good continues to be an unfortunate byproduct of the Instagram-age, it seems even the outdoor influencers are doing their best to respect and preserve the wilderness they adore and photograph. “I like seeing when people tag other people,” McCartney says. “It shows how an image can inspire people to hopefully take action in their own lives—to get back to nature where we all came from and all belong.”

Despite the facts: that it continues to be difficult in the 21st century to get back to nature and blending nature with technology is always tumultuous, the wave of outdoor Instagrammers in Upstate, NY seems to be, for now, full of surprisingly positive potential.

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