The History of Canada Hill

CANADA HILL-EARLY ABODE OF WILD ANIMALS

from “Sketches of the History of Windham, Maine 1734-1935 by Frederick Howard Dole (1935)

“The hill is said to have taken its name from the following circumstance. About 1770, William Mayberry, called "Cash Bill," cleared a farm on the southern slope of the hill and built a house and barn, the traces of which are still to be seen about ten rods from the road and nearly halfway to the summit. When the barn was raised, they had a pretty lively time. Rum flowed like water; all and sundry became more or less intoxicated and boisterous. While the revel was at its height, a man named William Elkins in a foolhardy spirit climbed the highest tree, an immense pine, growing nearby. When asked how far he could see, he replied with drunken gravity, "All over the world and a part of Canada." A bottle of rum was then smashed against the trunk of the tree, and the hill was named Canada Hill. CANADA HILL LET IT REMAIN. LET IT NOT BE CALLED HIGHLAND CLIFF, AS SOME OF A LATER GENERATION WANT TO CALL IT.

It Happened in Windham: Scenic Canada Hill – beautiful views with an interesting history by Haley Pal via the Portland Press Herald, August 20, 2021