On April 27, 1885, the S. S. Alpha, a steamboat which hauled freight and passengers out of Winnipeg along the Red-Assiniboine river system, set sail from Winnipeg with a cargo of freight for Portage la Prairie and Brandon. The Assiniboine River was high with spring runoff and the captain decided to cut across some of the river's many bends. She hit a sandbar, 11 miles north of Littleton. Abandoned to the river, Alpha gradually deteriorated and her resting place was concealed and forgotten. In the 1930s, a change in the river's course carved away debris, and when the water level is low, her remains can still be seen.

 Founder Robert Little was thought to be the first European settler to cross the Tiger Hills with a wagon, as he moved his possessions via Emerson from Ontario in 1879. The community he founded with his brother Nathaniel, was "missed by a mile" by the railroad; so Littleton was moved and re-named, Cypress River, in 1885.