Our Grandfather, Hugh Kaleihaleopuna Montgomery(1872-1953) was for many years Kauai's jail keeper, first at the old Nawiliwili jail, once located atop the bluff overlooking Nawilwili Bay, where the bulk sugar storage warehouse presently stands, and later at the jail that replaced it in 1936, nicknamed the "Montgomery Hotel, located across the Wailua golf course. The jail was demolished in the 1978 and replaced with the current Kauai Community Correctional Center.
Prior to taking on the job of Kauai's jailer, Montgomery, who with his cordial smile and sparkling eyes was a most unlikely looking jail keeper - had played clarinet with the Royal Hawaiian Band that had toured the U.S. mainland during 1895-1896. Founded in 1836 by Kamehameha III, the Royal Hawaiian Band was led at that time by Prussian born Henri Berger, a naturalized Hawaiian subject and close friend of Lydia Dominis, even before she became Queen Liliuokalani, Berger and his 38 musicians sailed from Honolulu to San Francisco on June 15, 1895. Upon arrival, they played for business magnate John D. Spreckels, who paid for their passage, as well street concerts, charming those in attendance with their beautiful music. They also played at fairs, alternating with the world famous composer and conductor, John Phillip Sousa, renowned for his military and patriotic marches. They also played in Dallas and several other cities and finally worked their way back to San Francisco with the Ringling Brothers Circus. They returned to Honolulu on December 22,1896.
Credit: Oahu Publications