The early log house building techniques practised in what is now Ontario were predominantly informed by Scandinavian architectural traditions rather than English, French, or Indigenous ones. Descendants of the 17th-century Swedish settlers of Pennsylvania who migrated to Upper Canada in particular brought with them many of the jointing and insulating styles present in this region's extant log cabins, while any six-over-six sash windows or 15 by 16-foot floor plans derive from traditional English cottage design.

While The Log Cabin at Guild Park along the Scarborough Bluffs lacks the distinctive "Swedish Key" log joints used to construct Exhibition Place's 1794 Scadding Cabin, it bears all the other hallmarks of Southern Ontario's early vernacular European architecture. According to the Canadian historian Marion MacRae, the original inhabitants of these modest homes considered them to be outside the realm of aesthetic expression: "That anyone would ever consider log houses admirable to the point of wishing to preserve them was inconceivable to the 18th-century mind."

There have been several decades of debate about when and by whom The Log Cabin at Guild Park was built. Twentieth-century consensus was that the cabin was constructed in 1795 by Lieutenant-Governor John Graves Simcoe's Deputy Surveyor General, Augustus Jones. More recent investigations, including an 1996 archaeological excavation of the structure's surroundings by the University of Toronto's Marti Latta, suggest that the builder may have been mid-19th-century farmer William Humphreys.

According to Friends of Guild Park President John P. Mason, the cabin's log jointing style is indicative of 1850s craftsmanship. He also notes that surveyors such as Jones were constantly on the move and thus would have inhabited temporary housing such as tents rather than structures as permanent as log houses. Based on these factors, Mason argues that Humphreys built The Log Cabin at Guild Park during the 1850s.

In 1803, King George III granted the lands on which the cabin sits to the United Empire Loyalist William Osterhout for his services with the Butler's Rangers provincial regiment during the American Revolutionary War, hence the cabin's former name. The cabin was later part of the Guild Inn Estate and is currently encompassed by the Guild Park and Gardens.