Long Trail to Skyline Pond

This out-and-back route along Vermont’s Long Trail begins at Middlebury Gap Trailhead and heads north into the Green Mountains, traversing a rugged and remote stretch of alpine forest. The route follows the ridgeline past exposed roots, steep climbs, and narrow tread, eventually ending on the junction for Skyline Pond Shelter. From the start, the trail climbs quickly toward Burnt Hill before continuing on the ridgeline. Boyce Shelter lies a little past the halfway point, offering a stopover option for backpackers. Expect several seasonal water sources throughout this stretch, but the most consistent can be found near the start or Skyline Pond. The route finishes on the spur trail to Skyline Pond Shelter, with access to camping and the pond. Moose tracks, bear activity, and ticks are all common along this route, so plan accordingly.