When we think of pioneers on the Allegheny frontier, and how it was that they passed the long winter months, our imaginations may have been influenced by having seen too many old-fashioned paintings of frontier life, such as the famous one by Eastman Johnson showing a young Abe Lincoln reading by firelight, or too many tv-episodes showing Fess Parker & Patricia Blair as Daniel Boone & Rebecca warming themselves before a stone fireplace.
The truth was often more austere. Certainly, newly-arrived immigrants from the east, face to face with the daunting perils and hardships of the frontier for the first time, wanted above all the comfort and security of a sturdy cabin for themselves and their families, but such a cabin was not easily had. Constructing a heavy log building with hand-tools, while using only materials gathered from the forest, required a set of specialized skills not easily mastered, and which many settlers had mastered only in part. If the newcomers arrived in number — as in the case of the Pricketts, with their large family — then their skills could be pooled and a cabin erected fairly quickly. But if the family was small — say perhaps only a husband and wife without grown children — then the labor of building a substantial cabin could be accomplished only with difficulty. Other more crucial tasks would need to be tackled first: securing a ready supply of food, water and firewood, planting a crop, and raising defenses against possible incursions from Indians, wolves or bears. Since a cabin could not be built immediately, they would have to make do with a temporary shelter.
Such an abode could take many forms. If a family was especially fortunate, they might stumble across a spacious cave, or perhaps a rock overhang set into a cliff face (such a place might already be inhabited by a bear, of course, which could be either good or bad news . . .). Many families set up house-keeping in caves for weeks or months at a time, and wintering over in a cave was not the worst of prospects, especially if the cave were set deeply into a hill and its temperature moderated by the earth itself.
Even a hollow tree might do in a pinch. Near present-day Buckhannon two brothers, the Pringles, during the 1760s, made their home in a great old hollow sycamore for two years as they eluded both Indians and the British army, from which they had deserted. It is impossible to say how many other settlers may have resorted to such a primitive solution. The Draper manuscripts mention one Thomas Spencer who lived in a hollow sycamore near Castalian Springs in Sumner County, Tennessee during the frontier years, and for every tree-dwelling frontiersman who made it into the written record, there must been many more who did not (I lived in a hollow tree myself in the Pacific northwest during a period of hard times many years ago — but that is another story). For the Pringle brothers, such an abode had the considerable advantage of being all-but-invisible to passing Indians and British soldiers alike, and this in itself would constitute an advantage to any settler. A chief disadvantage is that such a shelter could never be overly large, but if the Pringle brothers could get along in a tree for two years, then persumably so could a married couple. Another advantage afforded by a hollow tree is that it could be rendered habitable with a minimum of preparation, while its relatively small size and natural insulation would make it easy to heat with only a very small fire. If the cavity extended up into the tree (as is often the case), it might open out through one or more knotholes, thus comprising an effective and nicely-concealed chimney. The draft could be improved by cleaning out the cavity and enlarging the knothole.
How well a family was able to prepare for the coming of winter depended more than anything on what time of year they arrived. Spring was of course ideal. March might prove too early and liable to subject the pioneers to late-winter storms or blizzards. April could still bring on its share of inclement weather, but settlers would need as much lead time as possible to prepare land for planting, build shelters and the thousand other tasks necessary to making a new life in the wilderness. If you were not prepared to plant by mid-May at the latest, your entire crop, upon which you would depend next winter, might be in jeapordy. Nonethelss, there were many who came to the frontier without the luxury of being able to choose the best season of the year for doing so. Among immigrants to the frontier there were always a certain number of fugitives from the law, from creditors, or religious persecutors. There were run-away slaves, indentured servants, or simply flat-out-of-luck losers desperate for one more chance. Such individuals rarely were able to pick and choose the best time to “light out for the territory” and might very well find themselves poorly equipped and on the wrong side of the Alleghenies with winter coming on and not a friendly face in sight.
For such unfortunate and ill-prepared individuals or, say, for the careful family whose summer had nonetheless brought more bad luck and setbacks than constructive progress, the prospect of facing a wilderness winter without the protection of a sturdy cabin might be unavoidable. If no cave or hollow tree could be found, and there was not time or erect a proper cabin, the expedient alternative was to build some manner of half-face shelter.
These were generally eight or ten-foot-square structures framed with poles — sometimes with low log walls — and often set back against a large fallen log or rockface. They were closed on three sides, with a roof that always sloped to the back, and with the high side always open. They could be roofed with a variety of materials: blankets, hides, puncheons, or sheets of hickory or ash bark, and were floored variously with packed dirt, bark or dry leaves. In front of the open side a fire would be kept always ablaze, unless the weather were so inclement that closing the open side with hides of blankets proved necessary.
Such primitive shelters were only barely adequate if the winter was a hard one, and one can imagine that no effort was spared to erect a cabin before winter arrived in force. Often this meant that a family might have finished the walls and roof of the cabin, but have been unable to complete the chimney. In such cases an opening would be left in the roof and the fire built directly on the floor. Travelers through western Virginia before the Revolution noted many such cabins and described them as miserable hovels. They dreaded having to spend a night in them crowded among a strange family, but compared to a cave or half-face shelter, even the most primitive cabin must have seemed spacious, secure and warm.

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Very good reading! Thank you!