John R. Isom, superintendent of the Albemarle-Charlottesville Regional Jail, announced his plan to retire in January.
At 61, Isom did not cite any particular reason for leaving.
Isom succeeded former Superintendent Albert A. Tumminia in 1997.
Tumminia resigned during a period of low employee morale, state safety violations and two inmate suicides.
Prior to his position at the local jail, Isom served as director of the state crime commission and as sheriff in Loudon County.
Isom also served as a Fairfax County police officer for more than 20 years.
Officials at the Albemarle-Charlottesville Regional Jail currently are seeking a new superintendent.
--Comp. by Natasha Altamirano
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