The first written record of a European crossing the Cypress River was in Alexander Henry’s diary of August 11, 1806.
Holland was named after the first postmaster, Mr. A.C. Holland.
Landseer was named in 1904 after the noted English animal painter, Sir Edwin Henry Landseer.
Littleton’s founder, Robert Little, is thought to be the first European settler to have crossed the Tiger Hills area with a wagon during a move in 1879. In 1885, the railroad "missed Littleton by a mile”; the settlement moved a few miles south west, and was named Cypress River. The community describes itself as the "Best ‘Little Town’ on the Prairie”, which is a play on the name of Robert Little, and his brother Nathaniel Little. Littleton’s site is now marked with a cairn, erected in 1995 by the Cypress River Agricultural Society during their centennial year.