[1][3][4] The younger Holliday received a public school education, graduating from Allegheny College in Meadville, Pennsylvania, where he studied law, in 1852.

Although he moved to Kansas in 1854, Allegheny College's alumni records show Holliday receiving a master's degree in 1855.

He soon followed the many others making the migration to settle land west of the Mississippi River, but Mary stayed behind in Pennsylvania.

On December 10, 1854, after helping to find a location for the new townsite of Topeka, he wrote a letter to his wife saying: I am now thirty miles above Lawrence on the Kansas River assisting in starting a new town.

So I think it must be, and in a few years when civilization by its magic influence shall have transformed this glorious country from what it is now to the brilliant destiny awaiting it, the Sun in all his course will visit no land more truly lovely and desirable than this.

In the 1890s he became mistakenly convinced that Ellis and Trego counties in central Kansas contained mineral deposits of tin, zinc, and gold.

In 1899 his son Charles K. Holliday founded Smoky Hill City, Kansas, near the supposed mineral deposits.

In 1859 he singlehandedly wrote the charter for the Atchison and Topeka Railroad Company, which would connect the two cities by rail following the route of the Santa Fe Trail.