He attended St. John's Literary Institute of Frederick from 1850 to 1856, and Mount Saint Mary's College from 1856 to 1861.

He practiced law in Frederick, until he was appointed concurrently Chief Judge of the Frederick County Circuit Court (Sixth Judicial Circuit) and Associate Judge of the Maryland Court of Appeals in 1887.

He was promoted to Chief Judge of the Court of Appeals in 1896, where he served until his death at his home in 1907.

While serving as Chief Judge, McSherry was a member of the executive committee of the State House Building Commission.

The Committee oversaw the construction of the present day annex to the Maryland State House.