Dear Leap Overlook via Sherburne Pass Trail

This short but rewarding walk climbs to one of the best quick viewpoints in the Killington area, following the Sherburne Pass Trail to the spur for Deer Leap Overlook. Despite the modest distance of about 3 km / 1.9 miles round trip, it feels more substantial than a simple stroll because the route gains roughly 100 m / 330 ft and includes a steady uphill start, uneven footing, and a few rocky sections near the overlook. The trailhead is at the Sherburne Pass parking area on US Route 4, directly across from the Inn at Long Trail, near 709 Route 4, Killington, Vermont 05751. (innatlongtrail.com)

From the parking area, the route begins on the north side of Route 4 just east of the inn, climbing gradually through mixed forest on the Sherburne Pass Trail. This path is historically significant because it follows part of the older route of the Long Trail and Appalachian Trail through Sherburne Pass before later relocations shifted sections of the footpath. The Long Trail itself, maintained by the Green Mountain Club, is recognized as the oldest long-distance hiking trail in the United States, and this area preserves a small but meaningful piece of that hiking history. (en.wikipedia.org)

What to expect on the climb

The first section is the main work of the hike. Over roughly 0.8 km / 0.5 miles, you gain most of the elevation on a well-used forest trail that can be rooty, damp, and a little slick after rain. The grade is manageable for most hikers with moderate fitness, but it is enough to justify the medium difficulty rating, especially for anyone carrying children or hiking in wet weather. After reaching the junction with the Appalachian Trail/Long Trail corridor, the route continues briefly before branching onto the Deer Leap spur, which leads to the overlook. Sources describing the area place the overlook spur at about 0.25 miles / 0.4 km from the main junction, making the overall outing a compact climb with a fast payoff. (alltrails.com)

The forest along the way is part of Green Mountain National Forest and includes attractive northern hardwood and birch stands. The approach is enclosed and shaded, so it often feels cool even on warmer days. In shoulder seasons, fallen leaves can hide rocks and roots, and in spring the trail may be muddy. Trekking poles can help, though for a hike this short many people simply rely on careful foot placement. If you want turn-by-turn guidance, HiiKER is the best tool to have loaded before setting out.

The overlook and notable landmarks

The reward comes quickly at Deer Leap Overlook, a dramatic rock outcrop above Sherburne Pass with open views toward the Coolidge Range and the surrounding mountains near Killington and Pico. On clear days, views extend westward far beyond the immediate ridgelines, and some local trail descriptions note that the Adirondacks can be visible in the distance. The ledge is the defining landmark of the hike and the place where most walkers will want to pause, snack, and take in the panorama. (fs.usda.gov)

This is not a broad, fenced viewpoint platform but a natural cliff-edge setting, so extra care is needed in wind, rain, or when hiking with children. The rock can be slippery when wet, and winter or shoulder-season ice can make the ledge hazardous. Give the edge plenty of respect and avoid crowding near exposed sections.

Nature and wildlife

Because the route sits within the Green Mountains, hikers may encounter a range of northeastern forest wildlife. The broader forest supports species such as black bear, white-tailed deer, moose, wild turkey, coyote, and ruffed grouse, while cliff habitats in the region are also associated with peregrine falcon management and monitoring. In practice, most hikers are more likely to notice birdsong, squirrels, chipmunks, and signs of larger animals than the animals themselves. Ticks are also a consideration in Vermont, especially in warmer months, so long socks, a post-hike tick check, and basic insect protection are sensible precautions. (en.wikipedia.org)

Although this is a short day hike rather than an overnight trip, it is still worth following good wildlife habits: keep food secured, pack out all trash, and do not feed animals. Black bear awareness is especially relevant in the Green Mountain National Forest. (greenmountainclub.org)

Getting to the start

By car, the simplest approach is via US Route 4 at Sherburne Pass in Killington. The usual reference point is the Inn at Long Trail at **709 Route 4,