Historian Gordon B. Dodds stated, His works on the Yellowstone, the fur trade, and on Missouri River steamboating were long recognized as definitive....His style was formal, clear, and undramatic.

'[1] Chittenden also wrote the noted work History of early steamboat navigation on the Missouri River: life and adventures of Joseph La Barge.

[3] In 1878 Chittenden accepted a scholarship to Cornell University and an appointment by his congressman to the United States Military Academy at West Point.

After attending Cornell for two terms, he studied literature, languages, and history briefly at Ithaca, New York before transferring to West Point in 1880.

Steaming down the Hudson River on the Vibbard, Chittenden arrived at the United States Military Academy at West Point.

From 1899 to 1906 Chittenden held several posts concurrently and was assigned to a number of projects that kept him moving to different regions, eventually bringing him to Yosemite National Park in the far west.

Chittenden was requested by Hitchcock to take on the task and assume the role of senior member on the commission to study the Yosemite region.

Along with Chittenden, R. B. Marshall, a topographer, and Frank Bond, from the United States General Land office were also members of the commission.

Since the Federal government had jurisdiction over the navigable waters, congressional approval was necessary to commence work on the project and would inevitably require Chittenden's involvement.

[10][11] Chittenden's outlook over his remaining years in the service changed when an order issued by President Theodore Roosevelt a famous veteran cavalry man himself, that the annual physical exam require each officer to pass a fifty-mile test on horseback, or face retirement.

Chittenden was anxious of the test because his health was not the best due to his arduous service fraught with perils, including typhoid fever, causing gradual paralysis of his legs and attacks of nervous exhaustion.

The board subsequently referred the matter to senior officer General Adolphus W. Greely, who left the decision to Chittenden.

[15] In 1896 Chittenden decided to write an account of steamboat wrecks that occurred on the Missouri River in an attempt to determine which types of improvements for navigation were needed.

Searching for information he met the retired Joseph LaBarge, who had an extensive and often first-hand knowledge of steamboat history on the Missouri River.

[14] In June 1916, Chittenden penned a letter to the editor of the New York Times, praising the U.S. Congress for passing the Randall-Humphreys bill by a huge margin.

When Germany continued its unrestricted submarine warfare campaign he wrote "I hope so" to the prospect of the United States entering the war.