The Kelly Hollow Trail itself is a loop, which makes for some good options. In fact, there’s a short loop that’s less than three miles and a longer one that’s four miles. Along the way you’ll encounter a range of interesting places for such a short hike. From the parking area, the trail crosses the small stream, then goes along an old road through a Norway spruce forest. These trees were planted back in the 1930s when the Civilian Conservation Corp was active, and today they make for a unique hiking experience. (You’ll see the sign for the “cut-off” for the shorter loop on your right, which dips down into the shady and rocky ravine before rejoining the big loop again.) Steadily but gradually climbing, the road emerges from the evergreens and eventually hooks westward at a stream crossing. After a slight incline, the trail levels, rounds a ridge, and arrives at the Kelly Hollow Lean-to. The lean-to not only offers overnight accommodations, Catskills style, but it’s next to Beaver Pond, which often lives up to its name due to the presence of tree-gnawing residents. And there are frogs, newts and good bird watching. This spot, some two miles from the parking area, makes for a good family overnight.
The trail then rounds the upslope side of the pond, giving a good feeling of being at the head of the hollow. The trail also happens to be one of few marked cross country ski trails in the Catskills. Up until this point, the trail has been relatively easy for the back country skier, but between the pond and the road this second half of the loop requires more advanced skiing skills. Descending, steeply in places, the trail makes a couple of switchbacks before coming to the junction with the shorter loop. If you take this loop (by turning right) it will rejoin the outer loop and return to the parking area. If you stay left, you will complete the larger loop; however, you will come out at the road about a quarter-mile west of the main parking area (the one with the brown and yellow sign). Not far before the road you will also see an old cemetery just off the trail to your left.
As far as Catskill hiking goes, Kelly Hollow is relatively easy; yet whichever loop you choose, there’s enough elevation gain to break a good sweat and there’s plenty to discover along the way.
[The Kelly Hollow Trailhead is located on the right side of Millbrook Road, just over five miles from the intersection of Millbrook Road and the NYC Board of Water Supply Road along the south side of the Pepacton Reservoir. If you’re coming from Arkville, take Dry Brook Road six miles to Millbrook Road, turn right, and go 6.6 miles; the trailhead will be on your left. Although not required, it’s a good idea to have the set of Catskill Trails hiking maps, available at: www.nynjtc.org/product/catskill-trails-map-set]