He matriculated to Transylvania University in Lexington, whose campus now occupies the former site of his boyhood home, which had been built by his father.
After the building's completion, Gideon moved to Louisville, but Cincinnatus remained in Lexington, working as an employee of an architect named John McMurtry.
Under McMurtry's tutelage, Shryock developed a taste for the Tudor Gothic and Gothic revival styles, which were very popular during a series of revivals in architectural styles in the 19th century, particularly in Great Britain and the United States.
During the 1840s and 1850s, McMurtry and Shryock's practice catered to wealthy Bluegrass landowners who fashioned themselves after Scottish knights from Sir Walter Scott's literature.
One of Shryock's most notable buildings is the First Presbyterian Church in Lexington, a Gothic revival structure built in 1872 and located on North Mill Street.