Henry Charles Olmsted was born in Philadelphia on January 11, 1853, the son of Edward Olmsted and Catharine Ann Nisbet. Hery Olmsted entered the University of Pennsylvania in 1868 as a member of the College Class of 1872. He was president and regent for the Zelosophic Society as well as president of his class senior year. He was also a member of the Delta Psi fraternity.
After graduation, Olmsted went on to serve as Chief Deputy Sheriff of Philadelphia between 1888 and 1890, Chief Reporter for the Supreme Court of Pennsylvania and of the Orphans’ Court of Philadelphia County for the Weekly Notes. While Olmstead enjoyed a lucrative law practice as well as an effective political career, he was also an active Penn alumnus. He served as one of the directors of the newly incorporated University of Pennsylvania Athletic Association in 1882 and was a member of the Central Committee of Alumni until his untimely death in 1893.