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 (between Cypress River and Holland). 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.
Built in the late 1880s, the Union Hotel at Cypress River was advertised as the "best Temperance Hotel in the west". Since 1922, the building has served as a grocery store; currently the Lucky Dollar.
Prior to 1877, the political boundary of the border of the Province of Manitoba and the Northwest Territories was formed along an imaginary line 8 miles west of Gladstone and 1 mile east of Cypress River.