Wootton married multiple times throughout his life. His first marriage was to Maria Dolores LeFebre of Taos, New Mexico, in 1848. Maria Dolores, daughter of a French trader named Manuel LeFebre and a local Taos woman, died in childbirth in 1855 after bearing four children. Around 1857, Wootton married Mary Ann Manning and moved to the nascent settlement of
Denver, where he operated a saloon, hotel, and general trading and loan business. After Mary Ann's death in 1861, Wootton returned to southeastern Colorado and took up farming near
Pueblo, Colorado. In 1863, he married Fanny Brown, who died shortly after giving birth to a daughter. On June 17, 1871, Wootton married sixteen-year-old Maria Paulina Lujan of Mora, New Mexico. The couple had ten children together, six of whom survived to adulthood. Maria Paulina outlived Wootton by more than four decades, dying in 1935. == Military service and conflicts ==