[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.

[28] The transit district's $2.35 million financing plan, using a local property tax, was rejected in May 1980 by a margin of 64 votes.

[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.

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.