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Ashby Gap Lean-to is situated in a clearing near the summit of the Blue Ridge on the northwest slope, a little over a mile south of Ashby Gap. It is close to the site of an old cabin.
In 1938, the National Park Service published guidelines on the proper types of structures that should be built in the national parks. This booklet, authored by the architect Albert Good, was used by leaders of the Civilian Conservation Corps as guidance for the trail shelters they built along the Appalachian Trail during the 1930s. The description of the lean-to design reads, in part:
In New York State the Adirondack shelter is a tradition, a survival of the primitive shelter of the earliest woodsmen and hunters of this region. The end and rear walls are tightly built of logs, the front is open to the friendly warmth and light of the campfire. The roof slopes gently to the rear and sharply to the front to give a protective overhang.
The Adirondack shelter design was also used by the Appalachian Trail Conference in its guidance to member clubs in 1939 about the shelters they were building in the stretches of of the Trail they were responsible for.
In 1939 the Appalachian Trail Conference issued guidelines to its member clubs regarding the construction of shelters (then called lean-tos) along the Appalachian Trail. The goal, as stated in this document, was to place shelters approximately 10 miles apart:
Such spacing avoids undue exertion for travelers carrying heavy packs and yet permits "skipping" a lean-to by more strenuously inclined traveler's for their day's journey.
The design of the lean-tos was to follow the general design of the Adirondack shelter: three-walled, with a steeply sloping roof, and a stone fireplace at the front that would radiate heat into the structure.