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300 Miles in Prevail: An Epic Catskills Bikepack

300 Miles in Prevail: An Epic Catskills Bikepack

In July 2025, I loaded up my OPEN WI.DE gravel bike and headed north for four days of solitude, self-sufficiency and exploration in the Catskill Mountains. My journey traced the Catskill Bikepacking Route, a 270-mile loop with nearly 21,000 feet of climbing, linking remote gravel, rugged forest roads, and quiet Catskills hamlets in one of the most ambitious off-road routes in the Northeast.

This would be my first bikepacking trip since taking on the Vermont Super 8 last Fall, and I wanted to strike the balance between rugged off-road challenge and taking things at my own pace outside of a race environment. Nevertheless, I still found myself with my foot on the gas pedal as the hours got later and I strived to reach my daily destination goals before sundown. 

For three and a half days, I strived to pack minimally in terms of kit, opting to go with one pair of PREVAIL Bib Shorts and a technical tee considering the warm temperatures throughout the trip.

Designed by the New York Adventure Racing Association, the loop weaves together the most remote and scenic terrain in the region. For me, this wasn’t just a test of endurance, but a chance to connect with one of New York State’s oldest and most storied landscapes.

The Catskills have long existed in tension: wilderness and art, retreat and resilience. Originally home to the Lenape people, these mountains were later transformed by 19th-century tourism, painting, and poetry. Hudson River School artists immortalized the region’s misty peaks and dramatic waterfalls, while steam trains and stagecoaches carried New Yorkers into the hills for fresh air and escape.

That spirit of discovery still holds true, only now it’s accessed by fat tires and frame bags.

THE REGION

A landscape shaped by time. The Catskills aren’t just mountains, they’re a portal into the layered past of the Northeast. Originally inhabited by the Lenape people, the name “Kaaterskill” (often translated as “wild river”) still echoes through the region’s forests and streams. In the 19th century, the Catskills inspired the first major American art movement, the Hudson River School, whose painters captured the sublime in these misty ridgelines and rushing falls.

By the late 1800s, the Catskills were booming as a resort destination for urbanites seeking escape from New York City. Railroads, trolleys, and grand hotels followed. Though those days have passed, the spirit of retreat remains, especially when you leave the pavement behind and go deep.

THE ROUTE

The CBR officially begins & ends in the town of Ellenville, however my journey began in nearby New Paltz. The terrain features a mix of paved roads offering sweeping vistas of layered mountains, flowy gravel and doubletrack on historic rail trails, and intense gnarly hike-a-bike sections that traverse mountain passes where no road dare exist. The route offers ample resupply points through the first 200 miles, becoming more sparse on the final third of the route. Rugged wilderness transitions to expansive farmland and reservoirs that supply the New York City region. 

Day 1 – New Paltz to Windham

Distance: 82 miles

Elevation Gain: 6,000 feet

Ride Time: 8:43:29

Day 1 set the tone for what would be an arduous and exhausting journey through high heat and even higher humidity. Even before the ride started, a crackling thunderstorm tore the sky open and drenched my tent at 2 in the morning. I scrambled in the dark to zip down my rain fly and keep my gear as dry as possible. My helmet somehow managed to dislodge itself from the tent strap securing it and the padding was drenched as my ride began, the least of my worries.

The ride launched just after 7am, and following a quick pit stop for a breakfast sandwich at Stewart’s Shops, I made my way North on the Wallkill Valley Rail Trail, one of the best in the region, before crossing to the O&W Rail Trail. Step by step, the altitude increased and before long, the route meandered along the mystical Ashokan Reservoir. 

Flowy rail trails made way to the route’s first major test, the traversing of Overlook Mountain, a 3,000 foot peak on the southeastern edge of the Catskills. The ascent was fairly smooth and included a brief stop at the summit to take in the eerie landscape of the ruins of Overlook Mountain House. Shrouded in thick fog, the ruins represent a time long gone, when New Yorkers would make the challenging ascent to the mountain’s peak for a stay at what was once a luxurious hotel. 

This ascent led to the seemingly unending, barely rideable descent to Devil’s Kitchen, passing its lean-to along the way. The 4-mile descent is one of the most challenging on the route and I was elated to arrive in Tannersville in the late afternoon. A few more miles through scenic farmland until a short hike through the Elm Ridge Forest led to camp at the Elm Ridge Lean-to. By 8pm, the fire pit was raging, and the forest was quite aside from the distant calls of the Barred Owls. 

Day 2 – Windham to Delhi

Distance: 83 miles

Elevation Gain: 6,300 feet

Ride Time: 7:18:54

Day 2 was the most rewarding in terms of new roads covered and breathtaking views of the mountains, but also perhaps the most technically challenging hike-a-bike ascent of my life: Diamond Notch Trail. 

The trail is narrow, steep and rocky, carved out by centuries of water flowing from the mountain’s peak. A few sections were extremely difficult to get up and over, and carrying a 50-pound fully loaded bike only added to the challenge, requiring acute mental focus on each and every foot step. The views at the top were worth it, and the descent was relatively quick and straightforward. The extreme heat had me guzzling water from 3 bidons along the way, and required a stop on the descent to filter cold freshwater from the stream. 

The next 20 miles were marked by blistering heat on exposed paved climbs as the route led north towards the Catskills Scenic Trail - a flat, flowy doubletrack trail that cuts right through the heartland of the Catskills farming region. This unforgettable and fast section of the route eventually led to a few leg burning ascents to the evening’s campsite - the bikepacker-friendly Steady Slope Forest & Fields. 

I set my tent up on the high point of the property with a killer view of the mountain in the distance, and two doggos who kept me company for the entire night, even waking me up at 2am to bark at whatever wildlife lurked in the darkness of the woods beyond.

Thanks to Amanda and her husband for their kind hospitality, they have everything you need for a night out on a bikepacking journey. 

Day 3 – Delhi to Kerhonkson

Distance: 92 miles

Elevation Gain: 6,200 feet

Ride Time: 7:35:26

If the climbs of Day 2 were tough, the temperature of Day 3 was unforgiving, especially given the lack of resupply points along the day’s route. I arrived early in the morning in Andes, only to discover that all the markets and restaurants in town were closed. In dire need of calories and refuel, I decided to go off-route and head North to Margaretville. 

From this point on, the temperature was consistently above 90ºF and I was chugging as much water as I could. By mile 43, I was out of water and had no idea where to get it until by chance, I staggered across Ashley-Lynn’s farm stand at the Beaverkill Trout Hatchery. When I arrived, no one was around and there were no drinks in sight, so in desperation I walked around the back of the property and was greeted by Ashley-Lynn’s husband who opened up one of the sheds to find two full size fridges full of water and gatorade. 

We sat on the porch for a bit, hydrating and chatting about my ride, where I was headed and the ins and outs of operating one of the largest fish hatcheries in the state. The hatchery has been family run for 5 generations and hosts over 20 ponds stocking nearly 1 million fish. Still it seemed like a local family business with a well-oiled operation. The proprietor explained how was concerned about the fish’ health in the searing temperatures, which were well-above the ideal range for them. He also warned me, with total conviction, about the Sasquatch that inhabits the forest I planned to camp in that night.

Some hours later in my exhausted and dehydrated state, I doubled down on my research of accommodations in the area and discovered the Rustic Ridge View Farm. I texted the number and within minutes, was set up with a campsite for the night by the farm owner Wally. 

I arrived around 8pm after traversing the Vernooy Kill Forest, a close encounter with a rattlesnake and the remains of the ghost town confirmed my decision to venture onward and find a less creepy shelter for the night. 

Rustic Ridge View Farm is the perfect setting for a bikepacker’s evening under the stars. Jack the farmhand greeted me and showed me around the property, which is home to 16 horses and a wedding venue. I slept across from the horse pasture, literally steps from 2 horses who greeted me as I arrived. With the view of Minnewaska and the Shawangunk Ridge in the distance, I knew that I was near the end of my journey and closer to familiar roads. 

Day 4 – Kerhonkson to Poughkeepsie

Distance: 46 miles

Elevation Gain: 3,200 feet

Ride Time: 4:25:55

I packed up my tent for the final time on the trip and headed North for breakfast at the Kerhonkson Diner. I’d been searching for a classic diner the whole trip and finally found one. After a waffle and some eggs, I ventured south towards Ellenville to launch one last long ascent. This one I really have to call out NYARA for the terribly poor route choice of the 2-mile Smiley Carriage Road hike-a-bike up to Minnewaska State Park. This climb is completely unrideable and not the least bit necessary considering a gravel climb up to the same point is just a few more pedal strokes down the road. 

Hot take - I truly do not understand the appeal of hike-a-bike on bikepacking routes unless it’s absolutely necessary to get from one point to the other with no alternative. Hiking with your bike is not fun at all, I don’t care what you tell me. And in a race setting, what’s the point, to see who can walk faster? This section had me fuming, screaming, and cursing those who had designed the route. 

I eventually made my way up to Castle Point in Minnewaska, again out of water because of the sweltering heat, and made a quick pit stop at the Minnewaska Visitor Center. Familiar trails and carriage roads through Mohonk Preserve led to lunch at a cliffside gazebo to enjoy a Stewart’s Shops peanut butter and jelly hard roll. After ripping the descent off the ridge, I cruised back to Poughkeepsie and was on the mid-afternoon train back to NYC. 

Total Distance: 303 miles

Elevation Gain: 21,700 feet

Elapsed Time: 3 days, 6 hours, 59 minutes

KIT & GEAR

Kit: RUBBER N’ ROAD PREVAIL Bib Shorts, RUBBER N’ ROAD Trail Grid Tee, Trail Ripstop Shorts

Bike: OPEN WI.DE

Bike Bags: Restrap

Tent: Big Agnes Copper Spur HV UL1 Bikepack

Sleeping Quilt: Sierra Designs Nitro Quilt 35º

Additional Camping Equipment: Sea to Summit

IN MEMORY OF ADAM SCHAFFER

During my trip, I learned of the tragic passing of my sister’s best friend and a good family friend, Adam Schaffer, who passed away following a lengthy battle with ALS, aka Lou Gehrig’s Disease on Tuesday, July 29, 2025. 

Adam treated me like the little brother he never had. He attended Syracuse University with my sister, where I also eventually studied, and lived on my sister’s block in NYC after college. I always enjoyed spending time with Adam, and when he contracted ALS, I thought of him often during my time on the bike. This ride is dedicated to Adam’s memory, along with his endlessly warm & caring heart, and fighting spirit. 

CLOSING THOUGHTS

Despite having spent some time riding through the Catskills, I have never given it the appreciation as a riding destination it so rightly deserves. The roads are smooth, the views are breathtaking and the wildlife is vibrant and unforgettable. I caught my first bear sighting during this ride, in addition to spotting a rattlesnake on the singletrack and the variety of birds, horses and gophers.

The people of the region are warm, welcoming and ready to lend a helping hand to a cyclist in need. While there were ample resupply points, the heat certainly added to the complexity of this trip and I highly recommend bringing a compact portable water refill as there are plenty of streams along the way. 

If I had to do it all over again, I would reroute around the hike-a-bike sections because they’re just a waste of time and not enjoyable. Despite that point, I would certainly recommend this route to someone looking for a serious challenge and rewarding adventure not far from NYC.