19th Century History - Cheshire Academy Evolves

The school taught classical studies and entered a period of stability. An interesting fact is that even though the school was officially The Episcopal Academy, by the early 1800s, parents and boys addressed letters to The Cheshire Academy. This was seen in letters of graduate Samuel Welles to his son Gideon Welles (letter 1, letter 2), who would later become Secretary of the Navy under Lincoln.
The wooden baton used in all school ceremonial occasions is of tremendous historical significance from the Civil War period. The baton has a slim rounded head into which is set a horseshoe made of armor plate from the confederate vessel Merrimac. The handle is wood from the sloop USS Cumberland, one of the union ships taking part in the historic encounter. In 1917, Mrs. T.W. Darling of Virginia presented the baton to professor Eri Davidson Woodbury, captain of the first Vermont cavalry.

The mid 1800s produced two famous alumni: future industrialist J. Pierpont Morgan ’51 and General Joseph “Fighting Joe” Wheeler ’51, one of the youngest confederate generals of the Civil War.

Since the 1850’s, Cheshire Academy has become known as an international school. By 1857, over twenty Cuban students had enrolled as word of the Academy traveled by means of the agricultural commercial shipping business between New Haven and Cuba.

Around this time, the school enjoyed the solid leadership of headmaster Rev. Sanford Horton, who initiated new uniforms and built dormitories. Horton led the school for some thirty years and ushered in an era of quality education.

One of the most well loved teachers of this period was Eri Woodbury, for whom Woodbury Court and Woodbury Hall are named. He served in the Civil War and was present at the surrender at Appomattox in April 1865. He is buried in St. Peter’s Episcopal cemetery with a plaque commemorating him as a Congressional Medal of Honor recipient.
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