Sheriff Robert Ogden, the current Sheriff of Dukes County, was elected into office in 2017. Previous to that, Sheriff Ogden had been employed at the Dukes County Sheriff’s Office for 26 years, acting as Director of the Drug Information Bureau for 22 of those years.

Documentation of the first Dukes County Sheriff dates back to the 1600s when Dukes County was incorporated in 1683 as a province of the Colony of New York; at the time it included the island of Nantucket. In 1691, Dukes County was transferred to Massachusetts Bay Colony. The County was officially incorporated in 1695, without Nantucket, prompting the establishment of a regional authority; the first Sheriff of Dukes County.

“The Dukes County Sheriff’s Office remains one of the oldest law enforcement agencies in America.”

-The History of Martha's Vineyard V, Dr. Charles E. Banks

The original Dukes County Jail was built in 1808, where the current Registry of Deeds is today. Built of stone and brick behind a keeper’s house, the 20- by 12-foot, two-story jail consisted of four rooms. In 1875, under Sheriff Francis Smith, the original jail was removed and a new jail was constructed, with 12 cells that are still in use today.