He took a sabbatical to accompany his brother Bayard and his sisters on a grand tour of England, France, Germany, Switzerland, and Italy between July 1856 and June 1857.

He learned German and French and resumed his studies in the fall of 1857 but withdrew from Michigan at the end of the spring of 1858 to manage Hazeldell, seeking to make the farm self-sustaining through innovative agricultural methods.

Four companies, including Taylor's, were detailed to fight in the Shenandoah Valley campaign of 1862, attached to George Dashiell Bayard's flying brigade.

On June 6, 1862, Taylor fought in his first battle at Good's Farm near Harrisonburg, Virginia, where he was captured while leading a rearguard action.

Both officers were soon paroled, and Taylor spent the next four months in Annapolis, Maryland, waiting to be formally exchanged before he could rejoin his regiment.

Posted to defend Washington while his regiment recovered from its losses, Taylor received his anticipated promotion to full colonel on March 1, 1863.

Late in the afternoon that day, Taylor, on foot, led a charge down the hill across Plum Run, drove back the Confederates from a stone wall and through the Rose Woods to the edge of The Wheatfield, with the Bucktails in hot pursuit.

Taylor with twenty other soldiers got ahead of the main Union advance and halted, only to be struck suddenly by gunfire from Confederate reinforcements.