[3] Bus service in Salem was previously operated by the private City Transit Lines, which was granted a franchise by the municipal government.

[6] On May 24, 1966, voters in Salem approved a property tax levy to purchase the Capital Transit system and operate it under the municipal government.

[8] Under the new financing plan, which included increased fares, the bus system's operating expenses were stabilized and became eligible for federal subsidies to purchase a new fleet.

[11] The first new buses bearing the Cherriots name, colored white with red "cherry" trimming, arrived in Salem by late November and were put into service in January 1967.

[17] The formation of a mass transit district to serve a larger system, funded using payroll taxes, was approved by the state legislature in 1969 and implemented in Portland and Eugene.

[25] The existing Cherriots system was saved from proposed cuts after the approval of a two-year levy by Salem residents in May 1978.

[26][27] A third attempt at the formation of a mass transit district was put on the November 6, 1979, ballot, during the peak of the oil crisis, and limited to within the Salem urban growth boundary.

[29] The city-run Cherriots system was renewed by a one-year levy, funded by a smaller property tax within Salem, that was approved by voters in June.

[34] The approval of a $2.23 million tax levy in June 1982 allowed the Salem Area Transit District to take over operations of the Cherriots system on July 1, 1982.

[35][36] The system was funded by one- and two-year levies passed by voters in 1983 and 1985, until the approval of a permanent tax base on May 20, 1986.

[38] The current headquarters and operating base for Cherriots, located on Del Webb Avenue in Salem, was dedicated in April 1989 by Senator Mark Hatfield and Governor Neil Goldschmidt.

[46][47] The feasibility study, published in 2005, found that a three-to-four-mile (4.8 to 6.4 km) streetcar line would cost up to $61 million to construct.

In 2015, Cherriots started a "Moving Forward" plan which made new routes, including consolidations to achieve frequent service.

[57] The system's main hub is the Downtown Transit Center at Courthouse Square in Salem, located a few blocks from the Oregon State Capitol building.

[58] The transit center is also served by inter-county express service to Wilsonville, operated jointly by Cherriots and SMART.