The Shawangunk mountains (“Gunks”) are renowned for their beauty, accessibility, and opportunities for climbing and other outdoor recreation. There is one well-established ultra-distance FKT—the SRT (Shawangunk Ridge Trail). This FKT establishes another logical route, comprising the longest possible perimeter loop in the Gunks that doesn’t use any out-and-backs, bushwhacking, or public roads. In total, the route shows up as 51.2 miles on GPS (though is probably a few miles longer than that in actuality) and has about 8000’ of elevation gain.
Terrain goes from eminently runnable carriage roads to a few difficult rock scrambles, with a range of moderate-to-very technical and rocky trails in between. The route affords stunning views of the Catskills, the Hudson Valley, NJ, PA, and CT; goes by three sky lakes, an impressive waterfall, and more. Much of the run is spent among dwarf pitch pines, a rare habitat at this latitude. Water is available en route (and should probably be filtered), but reliable sources can be several hours apart, depending on the season and recent prrcipitation. Sensible bailout points can also be several hours apart. The route takes runners through some fairly obscure and difficult to access areas of Minnewaska State Park and the Mohonk Preserve, where one is likely to be alone most of the time, so standard wilderness safety protocols are important.
The Shawangunk Round can be run either clockwise or counterclockwise, and can start/finish at any of five trailheads: Jenny Lane (off of 44/55: walk from the lot to where the trail crosses the road), Sam’s Point Preserve (start from the visitor’s center), the Trapps Bridge at the start of Undercliff Road (park at the West Trapps trailhead lot and walk up to it), Pine Road trailhead (walk up to the ranger kiosk on Lenape Lane), Spring Farm trailhead (start at the ranger kiosk), or Coxing trailhead (start at the ranger’s kiosk). Parking at Jenny Lane is free. Sam’s Point Preserve requires a parking fee, and on weekends during peak seasons, reservations are necessary. All the other trailheads are in Mononk Preserve. Regardless of whether one parks at a Mohonk Preserve lot or not, using their trails requires a day pass or membership, which can be acquired at the Mohonk visitor center. For park hours, consult the websites for Minnewaska State Park, Mohonk Preserve, and Sam’s Point Preserve. NY/NJ Trail Conference maps of the Shawangunk trails are available—#104-106.
Taking the longest perimeter loop means that if one goes counterclockwise, the turns are always to the right unless a right turn goes onto a trail that does not connect back up to the trail network without turning around or taking a road. Correspondingly, if one goes clockwise, the turns are to the left. The route can be thought of in six segments between trail heads. The following list of trails is going counterclockwise, so everything would be reversed going clockwise.
1) Jenny Lane trailhead to Sam’s Point: Start at 44/55. Water is seasonally available just up the Jenny Lane trail. From Jenny Lane, R on Lower Awosting Carriage Road (water available at Lake Awosting), R on Smiley Carriage Road, L on High Point Carriage Road, R on Loop Road to the Sam’s Point Visitor Center. There’s a water fountain at the visitor center.
2) Sam’s Point Visitor Center to Trapps Bridge: Loop Road (taking the Lenape Steps is optional but worth it), L on Verkeerder Falls Trail (this is also the SRT. Water is available at Verkeerder Falls), continuing onto Scenic Trail, R after Mud Pond onto Mud Pond Trail. The route is now in the Awosting Reserve and takes the Awosting Reserve Loop trail counterclockwise until R onto an unmarked trail that leads back to a R on the Scenic Trail/SRT. R on Hamilton Point Carriage Road, R on Millbrook Mountain Carriage Road, R on Gertrude’s Nose trail. Shortly before Gertrude’s Nose is a seasonal stream for water. After Gertrude’s Nose, the Millbrook Ridge trail runs all the way to the Trapps Bridge.
3) Trapps Bridge to Pine Road trailhead/Lenape Lane. Cross the bridge, R on Undercliff Road, R on Oakwood Drive, R on Glory Hill Trail, R on Glory Hill Road, R on Lower Duck Pond Road (water available at a stream crossing here), L onto Lenape Lane at the ranger kiosk.
4) Pine Road/Lenape Lane to Spring Farm trailhead. R off Lenape Lane onto Woodside Trail. Cross Mountain Rest Road onto the Northeast Trail (need to take a sharp L turn to stay on Northeast), R onto the Bonticou Crag rock scramble. Down off the Crag on the short Yellow trail, then R onto Northeast again to L on Clearwater Road. L on Table Rocks Trail to Farm Road and from there to the Spring Farm Trailhead.
5) Spring Farm trailhead to Coxing trailhead. From the ranger kiosk at Spring Farm, Chapel Trail (back onto the SRT), crossing Mohonk Road and Old Clove Road and L to enter Undivided Lot Trail, R on Old Minnewaska Trail to the Coxing trailhead. Just before the Coxing trailhead is the Split Rock swimming hole, where water is available.
6) Coxing trailhead to Jenny Lane trailhead. At Coxing trailhead, High Peter’s Kill, R on King’s Lane, which veers back around to R on High Peter’s Kill (water is available at the Peter’s Kill), picking up the Warwarsing Turnpike Trail next to 44/55. That connects back to Jenny Lane at 44/55.
It sounds very complex, and some beta scouting might be useful, but looking at a map should make intuitive sense of it. It's worth it.