A look back at Mohonk’s Undercliff/Overcliff Carriage Road Loop

Overcliff Carriage Road. (Photo by Gerald Liddelow)

“Stewardship is not an abstract concept. It means physical maintenance, ranger patrol, ecosystem research, long-range planning and constant evaluation…Because it is neverending, it is not a task for the faint-hearted or for those who seek quick satisfaction. It is like life itself, a process, and our only hope is to embrace the opportunity.”
— Daniel Smiley, founder, Mohonk Trust (now Mohonk Preserve)

“It is not wildlife that is in need of management, so much as man himself.”
– Frank Egler, “Wildlife Habitat Management for the Citizen,” 1967

One of the Mohonk Preserve’s most iconic routes is Undercliff/Overcliff, that oval-shaped 4.7-mile loop that takes visitors underneath soaring cliffs with rock climbers dangling above to the quietude of more forested Rhododendron Bridge and back along a meandering carriageway that opens up with breathtaking views of Clove Valley and rolling contours of the Catskill Mountains in the distance.


Paul Huth, who worked for decades alongside of Dan Smiley and later as the director of the Daniel Smiley Research Center at the Preserve, can attest to the timelessness of this loop, which was built between 1902 and 1928. He recently completed a report on a study titled “The Natural History of Undercliff Road,” which was compiled in 1968 by Dan Smiley and Frank E. Egler, a Nature Conservancy Board member and, along with Smiley, part of its first Northeast Chapter, chartered in 1954. “These two carriage roads, for me, capture the closeup and the distance, the grandeur of nature and the Shawangunk history and aesthetic,” mused Huth. “To the observant eye, they are timeless and yet are constantly changing. They can allow for an individual to get a personal outdoor experience at a light surface level, and if desired and needed, at a much deeper level. They are touchstones in time.”

Climbers and hikers at Undercliff Carriage Road. (Photo by Stephen D Stewart-Hill)

Snowshoeing on Undercliff Carriage Road. (Photo by June Archer)

Indeed, the almost-five-mile loop is a fan favorite for locals who love to test their mettle running clockwise or counterclockwise to measure their fitness. It’s also an incredibly popular route for walking, cycling and horseback riding. When it snows, it’s a haven for cross-country skiers and snowshoers. And these are the land-based activities. Up above on the conglomerate cliffs, climbers from all over apply their agility and skill to varying degrees of difficulty and vertical acuity, climbing one-, two- and three-tiered pitches that feature overhangs, fingernail-width holds and jaw-dropping heights. Sometimes they share those cliffs with their climbing partners, other times with sunbathing copperheads.

The construction of the lower carriage road, Undercliff, was such an undertaking for its time that it made headlines in the New Paltz Independent on August 22, 1902. “The sound of a great deal of heavy blasting is heard in our village,” the paper reported. “The blasting is on the new roadway which Mr. Smiley is building from Pine Hole [Rhododendron Swamp] to the Trapps Road [the Wawarsing and New Paltz Turnpike].” This was labor-intensive work and required heavy blasting, wooden lifting derricks and expert stonecutters.

Designing the carriage-road system became a real vision of Daniel Smiley, Sr., who after joining his brother Albert in the management of Mohonk Mountain House operations in 1881, set his sights on the creation of the carriage roads, their locations, views, natural features, and interconnectedness. There was a real emphasis on the aesthetic quality of Undercliff, which had to be constructed through heavy mounds of fallen talus. It provides stunning views of the Wallkill River Valley to the east, and as it meandered along the cliffs towards the south, glimpses of the Smiley Memorial Tower on Sky Top come into view.

“The various built features of the roads – the bridges, the supporting walls, altered rock outcrops – became touchstones connecting us with another time,” wrote Peter Manning, a Mohonk Preserve research associate in geography and landscape, in 2010.

In his report, Huth writes, “With the completion of the building of Minnewaska (Trapps) Road by Mohonk Mountain House in 1907, and the construction of a connecting bridge over the Wawarsing and New Paltz Turnpike at the Top-of-the-Trapps (now Route 44/55 above the hairpin turn), Undercliff Road provided part of a major and scenic route for Mohonk Mountain House guests traveling to and from Minnewaska.”

Overcliff Carriage Road was roughly carved out in 1912, but was not officially completed until 1928. Once the loop was in place, it gave guests different viewpoints as they traveled to and from Minnewaska and Mohonk Mountain House. The carriage drivers were often instructed to take visitors via Overcliff and then have them return on Undercliff, both of which provide exquisite but very different views of valleys on either side of the Shawangunk Ridge.

Trapps Cliff and Talus, predating construction of Undercliff Road, by Geologist N. H. Darton,
United States Geological Survey, 1892. (Collection Daniel Smiley Research Center, Mohonk Preserve)

From the very beginning the Smiley family envisioned a hotel and landscape that were intimately related to the existing geological and forested setting. When they set about building carriage roads, the existing terrain, wherever possible, was preserved to reduce labor and construction costs, but also to preserve the existing character of the environment and highlight its natural features, such as waterfalls, rock outcrops, sweeping views of the valley, pitch pine and hemlock forests, lakes, streams and areas of shelter, as well as wild exposure.

Because the roads were created primarily at the end of the 19th and beginning of the 20th century, they were also constructed with horses and carriages in mind. Many of them follow the curves of the mountains, and have a gentle gradient with wide-swinging curves and bends for the horses to be able to back up and turn around. Wide and evenly graded, they are lined by cut or fallen conglomerate boulders.

View of the Catskills from Overcliff Carriage Road. (Photo by Gerald Liddelow)

Undercliff/Overcliff Carriage Roads, which encircle a portion of the Gunks like a signature bracelet, appear to cut into the cliffs on one side and then almost dangle off the edge towards the valley on the other. As the roads meander toward Rhododendron Drive, they enter pockets of woods and moss-covered stones and a misted, mysterious pocket of the Preserve, until they reach back towards higher ground. There is a gentleness to these roads that unfold the landscape, view by view, allowing travelers always to be surprised by what’s around the next bend, their curves almost feminine, as if reaching to embrace the mountain.

Dan Smiley, Jr., a naturalist and land preservationist, carefully monitored, documented, archived, photographed and took intimate, detailed notes about everything, including temperature, rainfall, snowfall, flora, fauna, animal behavior, bird-nesting and beaver-lodge-building. He kept an eye on subtle, almost imperceptible changes in the ecosystem so that the Mohonk Trust, and later Mohonk Preserve, could have a database from which to see patterns emerge and dangers to reckon with. Besides carefully organizing and archiving his notes and systematizing daily temperature and precipitation records, Smiley set up a “window-in-time” project. He and the co-authors of the “Natural History of Undercliff Road” established 17 stations along the 2.3-mile road to take photographs and notes in hopes that every 15 years, later Preserve staffers would do the same – which they have.

The Near Trapps from Undercliff Road, Photo Station No. 2, 1968. (Daniel Smiley; Collection Daniel Smiley Research Center, Mohonk Preserve)

According to Huth and his intimate knowledge of these studies, as well as his five decades working and enjoying being part of this landscape, there have been some significant changes. The most significant is the negative impacts of climate change, including such “major weather events” as a devastating ice storm on November 16, 2002, which left nearly an inch of ice coating on tree limbs, causing heavy deciduous tree damage. “Increased weather variability, including frequency of larger-volume and sometimes shorter-duration precipitation episodes, as evidenced from significantly warmer temperatures as recorded in the 126-year-old Mohonk Lake Cooperative Weather Station, resulting also in long-term negative impacts to some northern native plant and animal species monitored for more than a century in the Shawangunks…”

Undercliff Road construction, 1902. (Courtesy Mohonk Mountain House Archives)

Other negative developments include the arrival of invasive species like the woolly adelgid, which has wiped out many of the Eastern hemlocks; the emerald ash borer, leading to heavy mortality among the native white ash; and the extensive spread of Japanese stiltgrass, first collected along the West Trapps Connector Trail in 1996. Huth also noted “increased recreational popularity and area use including hiking/walking/biking/climbing and more recently bouldering” – all influenced, he said, “by online resource availability, posted narrative experiences, intensely driven over the last year by the COVID-19 pandemic.”

On a positive note, the growth of grassroots environmental campaigns, such as the lawsuits forcing General Electric to clean up the toxic PCBs that it had dumped into the Hudson River, has contributed to the success of efforts to bring the peregrine falcon back to the Gunks to nest after near-extinction. 2002 marked the official return of the peregrine falcon to its historical eyrie location, last used in 1955. This milestone led to Mohonk Preserve staff and volunteer monitoring of nests, along with well-respected annual cliff climbing route closures during the breeding season.


View from Undercliff Carriage Road. (Photo by John M. Mizel)

This land holds it all: the footsteps and flights of so many creatures; the weight of snow and water and windswept cliffs, with pitch-pine roots wrapped through a crevice to hold on; the impacts of human industry – most of it damaging, some, like the fight for the peregrine and the insistence on land preservation, Herculean and hopeful.

Undercliff/Overcliff is a ring in the sky that seems to encircle life endlessly. Its beauty never fades, its surprises never dull and its history is held in the collective memory of all the life that it has held and continues to hold.