Born near Stella, Virginia, Penn moved with his parents to Lexington, Kentucky; he then completed preparatory studies and attended Emory and Henry College, Marion, Virginia.
Later he moved to the parish of St. Tammany, Louisiana, in 1821 and engaged in planting near Covington.
Penn was elected as a Democrat to the Thirty-first Congress to fill the vacancy caused by the death of John H. Harmanson.
He served as chairman of the Committee on Expenditures in the Post Office Department (Thirty-second Congress).
He returned to St. Tammany Parish and engaged in planting and the operation of a lumber mill near Covington.