Deer Leap Overlook Trail, Killington, Vermont

I left my wallet in Maine, but found my feet in Vermont.

This was my second hike up Deer Leap and my fourth trip to Vermont in less than a year, thanks to the trail guide I’m working on. Living in Portland makes for a long 3-4 hour journey to Vermont, but its one I’m willing to take - the mountains here are stunning.

This last trip was squeezed into a work week and since I was only able to take one day off, I’d planned one of my two hikes for the evening of my arrival - hoping to finish my descent before the sun made hers. In my haste to leave Portland right after work, I left my wallet at home, realizing this halfway to Vermont…right around the time I realized I was almost out of gas. I am not the most organized of planners.

As haphazard as I may be, things usually work out. Although I’d never used it, I had set up Apple Pay on my phone weeks before. Come to find out, everyone uses Apple Pay, even ramshackle gas stations in rural Vermont! I’m sure this is not news to you, but it was an exciting revelation to me. It also saved my ass.

I did finish my hike up Deer Leap before dark, enjoying stellar sunset views from the overlook.

This mossy trail bordered by birch trees offers a stellar reward for a short climb. The hike begins on the Sherburne Pass Trail, the former route of the historic Long Trail, then leads to a large rock outcrop with expansive views of Sherburne Pass, Pico Peak, and the north face of Killington.

Begin your hike from the Inn at Long Trail’s parking area, located on the north side of US-4. Built in 1938, this was the first lodge constructed for Vermont's ski community. While dogs cannot stay at the Inn, they do provide many services for thru-hikers of the Appalachian Trail and Long Trail.

The first section of this hike takes you along the Sherburne Pass Trail, once the official route of Vermont’s Long Trail. Although the Long Trail has been rerouted to the west, the Sherburne Pass Trail still links up with the Appalachian Trail before merging back with the Long Trail. Built between 1910 and 1930, the Long Trail is the oldest continuous footpath in the United States. It spans 272 miles and offers 70 backcountry campsites and 166 miles of side trails.

Large rocks and some road noise dominate the first 0.3 miles of the Sherburn Pass Trail, but you soon leave all that behind for a tranquil, shaded path. After walking just under half a mile, pass the junction with the Appalachian Trail before taking a left onto the Deer Leap Trail. From this point, the trail bears west through a birch forest carpeted with moss, then south towards Deer Leap Rock.

Before arriving at the rock outcropping, cross a short boardwalk and descend some wooden steps. The leash requirement for this hike becomes quite clear after stepping onto the large rock, which has steep drop-offs on many sides. Take in the spectacular views of Sherburne Pass, the Coolidge Range, and New York’s Adirondacks to the west.

For a longer hike to the Deer Leap Overlook, start at Gifford Woods State Park, located off Route 100 in Killington. From this trailhead, the route to the rock outcropping is 3.7 miles round trip. By adding the Deer Leap Mountain loop, you can extend the hike by an additional 1.3 miles, making it a total of 5 miles round trip.

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Less than 5-miles from the Deer Leap Trail is a short hike leading to Thundering Brook Falls, the sixth tallest waterfall in Vermont. The 0.5-mile out-and-back trail begins on a 900-foot boardwalk and leads to a platform overlooking a roaring section of lower waterfall, fed by 140 feet of cascades. The pools here offer numerous swimming opportunities for your dog, and the breathtaking falls make it a worthwhile visit.