Catskill Quests: Challenging Ourselves in the Great Outdoors

Challenging ourselves in nature need not require tests of physical strength or endurance, but taking a cue from someone known for great accomplishments is always an inspiration. So, I sat down for a few with fellow outdoor enthusiast Jamie Kennard to ask him what drives his journeys in nature. Kennard is well known as one half of the two-brother team to be the first people to ski the Catskill 35. For the uninitiated, the Catskill 35 refers to the 35 mountains of the Catskills that are higher than 3500 feet. Most tackle this test with hiking boots, but Kennard and his brother Doug are the first to do it on skis. They are also the second and third individuals to accomplish the same feat in the Adirondacks. The northern challenge includes the tallest 46 peaks of Adirondack Park, 29 of which are taller than Slide Mountain, the tallest peak of the Catskills. It took Jamie and Doug twelve years to complete the task in both parks.

Speaking to Jamie earlier this year reaffirmed something I’ve always felt about my own time in nature. The activity is the excuse, and any accomplishments achieved while engaged with nature are added enjoyment, not the reverse.

“I’m personally more driven by what I can do and less about what that end goal is. Can I do the thing today, can I do it tomorrow, can I do the next thing? As I complete more of these accomplishments that some people would label goal-oriented, I’ve come to slow down and appreciate the process of getting there, and that, for me, ends up being the more meaningful aspect. It’s everything in between and not necessarily the punctuation at the end.” – Jamie Kennard

I interpret Kennard’s spiritual relationship to his quests as more a tally of that which has been accomplished rather than a number he seeks to achieve. The essence of that premise is so beautiful and essential to how we may set our goals for time spent outside. I believe it is vital to bear in mind that if you engage in any of the quests described herein, the first step is the victory. Similarly, needing an excuse to maintain your engagement with nature is in no way inferior to just getting out as often as you can. Whatever drives you… get outside. The things you find on the trail and in the skies reflected upon the water will illuminate your own greater truth to yourself.

The Catskill 3500 Club

The Catskill 3500 Club was founded in the fall of 1962, inspired by a collection of enthusiasts who wanted to encourage hiking, education, and the “responsible conservation of our region’s natural resources.” The premise is simple. To join the club, summit the tallest “publicly accessible” peaks of the region, then re-climb four of them again in winter, and you’re in. This may seem a relatively simple one-step-at-a-time challenge but beyond one’s physical capabilities to go up, realize that about a dozen of the peaks have no trails or easily discernible summit. Hikers need to possess the mental skills and stamina of a true backwoods bushwacker to complete this quest. Check out their Hiker 101 Guide to learn more about the essentials of joining the club. Important to note that in recent years, two of the peaks were removed from the list as they sit on private property.

Additionally, the history of the 3500 Club’s work is an incredible chronicle of successful cooperative natural resource management. As someone who has spent a good chunk of the last two decades working on local watershed conservation issues, I’ve witnessed that true widespread cooperation isn’t always available when making decisions about land use. The 3500 Club, however, which didn’t receive non-profit status until 2022, was asked to help set a course for the management of public lands as early as 1966. Their principles for the preservation of public land as wild land are stated in their mission. “The motivating force behind the club’s activities has been the preservation of the Catskill Forest Preserve in its wilderness state.”

Variations on a Theme

Of course, there are numerous side quests and variations to the Catskill 3500. Check out these other hiking challenges.

• The Catskill 3500 as a Thru-Hike – Current record is 2 days and 9 hours
• Catskills Fire Tower Challenge – There are 6 to climb
• The Adirondack Forty Sixers – Go north

The Charmed Circle of The Catskills

The name may not imply it, but this is a fishing challenge. It’s possible you’ve heard the term first coined by Cecil Hecox in 1969, as it’s been honored through emulation countless times in the names of books, fishing events, and educational websites. It also adorns the top of the octagonal display case at the Catskill Fly Fishing Center & Museum. Hecox’s revolutionary two-part article, originally published in Outdoor Life Magazine, has likely inspired more anglers to visit the birthplace of American dry fly fishing than any other published article on the subject. Within it, Heacox paints a lush vision of the seven primary rivers of the Catskill Mountains: The Esopus, Schoharie, Beaverkill, Willowemoc, Neversink, and the east and west branches of the Delaware River. This timeless piece of writing outlines not only the rivers but the larger-than-life people and stories that have sustained the angling public’s thirst for fishing lore for over 50 years. I have heard this article quoted countless times, and in my re-reading of it for this article, I was reminded of a few more stories that I’d forgotten emerged from Heacox’s masterpiece. Most importantly, to me, it professes principles similar to that of The 3500 Club. Both the article and the experience anglers receive when visiting the Charmed Circle emphasize the conservation of rivers and the importance of public access to them. Heacox accomplishes this by promoting the work of individuals committed to the task. Anglers will learn this by taking in the wide array of landscapes, quiet hollows, and raging runs they’ll encounter while fishing the Catskills. It is a varied and uniquely beautiful region that will remain one of the premier trout destinations of the northeast – destined to survive the ravages of global warming.

The quest here is simple: catch a fish (preferably a trout… preferably on a fly) in each of the seven rivers of the Catskill Mountains. While this is essentially a challenge without rules, I suggest trying to do it within a year. One of the best parts of this challenge is the skills you’ll discover you don’t have, as fishing each of these rivers is a different experience requiring varying tactics and levels of skill.

Beyond the Creel Limit

Other obvious and not-so-obvious fishing accomplishments worth bragging about.

• The Trifecta: Catch a rainbow, brown, and brook trout in a single day of fishing. You’ll get extra credit if they’re all wild fish!
• 20 on a 20: This is strictly a fly fishing challenge. Catch a 20-inch trout on a size 20 fly. FYI, the hook of a size 20 fly is only five millimeters long!
• Species life list: Many of us are species-specific anglers, but others chase anything they can with a rod. Start a lifetime list of the fish you’ve netted. It’s simple fun that will likely lead you to the far corners of New York State, which boasts more than 165 recreational fish species anglers can enjoy.

The Hudson River School Art Trail

In my previous article, I spoke at length about the Hudson River School’s influences, exploring the impact that American nature paintings had on the birth of outdoor recreation. The Hudson River School Art Trail is a wonderful intersection of those concepts with the notion of a personal challenge. A beautiful view is an inspiration, and while it’s nearly impossible to find a subpar one in the Catskills, the locations chosen by the Hudson River School artists for their famous paintings are a hit list for all time.

A project of the Thomas Cole National Historic Site, the Hudson River Art Trail consists of twenty locations between Hastings-On-Hudson and Albany, where artists of the 1800s ventured to create iconic imagery inseparable from the history of our state and the country’s first truly American art movement. This 135-mile art trail will take you to the edge of waters and the tops of mountains. Some locations are a short walk, others a day’s hike. Visit the project’s website, which details the level of difficulty for each of the stops and offers insight into the history of the locations and the famous paintings made in the face of nature’s gaze.

Extra Credit

Once you complete the local 20, hit the road.

The Hudson River Art Trail outlines three additional locations within striking distance in Massachusetts and New Hampshire, but remember, the artists who began their work here in our beloved Hudson Valley migrated westward and eventually overseas. Find your favorite and plan a trip!

The End Proves Nothing

We venture off our regular course to learn. And quite often, when that path leads us to nature, it is something about ourselves that we intend to explore. Jamie Kennard says it succinctly when he states quite simply… “It’s a reason to get up in the morning.” There’s a subtle vulnerability in this statement that betrays our need to be in a place that, for all its beauty, ultimately presents us with a mirror, not an ideal. “Many go fishing all their lives without knowing that it is not fish they are after.” Thoreau’s version nearly absolves the addict, but whatever amount of time you can commit, explore your natural world with intention. However you are inspired to commune, make your time your ceremony. Honor something, even if it is your own accomplishment. There is wisdom in these hills.

Photos Courtesy of Todd Spire @toddspire + Jamie Kennard @catskilltracks
Featured photo: Jamie Kennard Fishing at Ashokan Reservoir – Photo by Todd Spire

Todd Spire is a contributing author and lives in the Hudson Valley, NY. To learn more about him, read his interview HERE.