The name "Similkameen" is said to have originated from the Similkameigh indigenous people of the region, meaning "treacherous waters".
The Similkameen is one of several historical regions of British Columbia whose foundations and settlement lay in the days of the Colony of British Columbia, and was one of the first areas of the province prospected as well as farmed and ranched.
The area has seen a number of famous gold strikes and large mining operations, notably the Tulameen Gold Rush of the 1880s and 1890s and the Nickel Plate Mine at Hedley, but also including coal at Blakeburn and Coalmont, and copper at Allenby and Copper Mountain, all of these locations in the vicinity of Princeton.
Richter's original 30 acres (120,000 m2) of fruit trees at Keremeos Centre are considered to be one of the two foundations of BC's orcharding industry, the other being started by the Oblate Fathers at Okanagan Mission.
Today, the area is seeing a burgeoning wine industry and a boom in sunbelt-oriented recreation housing and property development.