[4] At the age of 17, he purchased a one-way ticket to West Point where he passed the United States Military Academy admittance exam.

[12] In 1889, Crosby worked with Baltimore inventor David G. Weems to assemble a small experimental electric locomotive on a 28-gauge test track laid down in Laurel, Maryland.

He served as president of various local public utilities in Chester, Pennsylvania; Wilmington, Delaware; and Washington D. C.[15][16] In 1892, he collaborated with Louis Bell to publish The Electric Railway in Theory and Practice.

This contract was initially awarded to United States Electric Lighting, but Crosby was ultimately successful after a court challenge.

This began a commercial contest between the two companies, which came to an end in January 1889 when the stock owners of PEPCO acquired their rival.

He wrote a travelogue about his experiences titled Notes on a journey from Zeila to Khartoum, and this was published in The Geographical Journal in 1901.

[6] In 1903, Crosby began an extended trip to Asia, starting from London, travelling across Russia by railway to Turkistan, then by foot (in sometimes extreme conditions) to Tibet.

[2] In 1904, the Crosby family purchased a large property named the View Tree Farm, which covered 358 acres on top of Watery Mountain to the west of Warrenton, Virginia.

[2] At that time he was President of the Wilmington & Philadelphia Traction Company,[22] but resigned from this position in 1913[23] and retired from the railroad business.

Herbert Hoover asked him to become the director of relief work in France and Belgium, a post he accepted in March 1915.

[1] The United States joined the war in April 1917, and Crosby was commissioned with the rank of Major of engineers in the Army reserve corps.

In 1927, he would resume his international travel, making trips to South West Africa in 1927; Tanganyika, Kenya and the Belgian Congo in 1936; and Romania, Russia, Poland, and Germany in 1937.

He was a member of the Cosmos Club in Washington, D.C.[25] His collected papers are held by the Manuscript Division of the Library of Congress.