Sheriff, Frederick County Sheriff’s Office, VA

Sheriff Lenny Millholland was born and raised in Cumberland, Maryland. From 1977 through 1979 Lenny worked for the Allegany County Sheriff’s Office, in Cumberland Maryland.

In 1979, at age 21, Lenny came to Winchester, VA. and became a police officer with the Winchester Police Department. Lenny worked his way through the ranks as a Patrol Officer, K-9 Handler, Investigator, Sergeant and Lieutenant in charge of the Criminal Investigations Division. In 2002 Lenny became the Sheriff of the City of Winchester. This was a position that he held for 12 years or 3 terms. Sheriff Millholland ran for and was successfully elected as the Sheriff of Frederick County, VA. Lenny is currently the only Sheriff to have ever been Sheriff for a City, (3 terms) and then ran for, and successfully win the position as a County Sheriff. Sheriff Millholland is responsible for 415 square miles and over 90,000 residents. Sheriff Millholland commands 151 sworn law enforcement personnel, 10 office staff and 4 Communications personnel. Sheriff Millholland has been in Law Enforcement for over 43 years and was a K-9 handler for over 22 years, handling Patrol K-9’s and Bloodhounds. Sheriff Millholland is an FBI National Academy Graduate #188, Past President of the Virginia Sheriffs’ Institute and is currently the Secretary of the Virginia Sheriffs’ Association. Lenny is a graduate of the National Sheriff’s Institute and has been a mentor for the Sheriff’s Institute and The Federal Law Enforcement Training Center (FLETC).