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Deer Leap Overlook, Killington VT

• 4-star hike
• 2 mile out-and-back
• Moderate | Gain 500 feet
• Killington, VT | Central West
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Five people sit on a rocky outcrop overlooking a vast forested valley, facing a distant tree-covered mountain with visible trails carved down its slopes. The sky is mostly clear with wispy clouds, suggesting a calm, sunny day. The vantage point emphasizes the scale and serenity of the natural landscape.

Overlook vistas towards Pico & Killington Peaks.

Attracting hikers of all ages and abilities, this well-trodden route over quintessential New England terrain - tree roots and uneven rock - leads to spectacular elevated mountain vistas. For those concerned about the terrain, it’s worth noting that the early part of the trail is as difficult as it gets.

This is the shortest route to Deer Leap Overlook, beginning at a mostly concealed trailhead adjacent to a lodge and restaurant on the side of US Route 4 highway. Parking is available across the road at the free Appalachian Trail lot. Perhaps the hardest part of the route is navigating the highway crossing, which has no pedestrian considerations and, being on the crest of a hill, provides limited visibility of oncoming traffic in either direction. At least the road has a large central painted median.

Trail Options Expand KML · Google Earth ·

⬤ 4★ Inn to Overlook 1.9 mi out & back, moderate, gain 500 ft
GPX File · AllTrails · Directions GPX?

P Free parking

After a moment of confusion at the trailhead sign - which directs climbers and hikers in different directions, but we're not sure which - head to the right and begin your hike under cover of forest. Between here and the overlook there are two trail junctions, but all you need to remember is to keep bearing to the left and you can't go wrong.

The overlook rewards with sweeping 180-degree views of ski trails, and the lush Vermont countryside. The large granite ledge overlooks the north side of Sherburne Pass, offering views of nearby Killington and Pico peaks, with distant sights stretching to New York’s Adirondacks.