Monadnock Moment No. 168

Multi Era 5 - 7: 1860 to 1920s

Rough Rider of Winchester

In 1860, young Charles Wood postponed his medical studies to seek work in a Winchester, New Hampshire sash and blind factory. It was there, in a Main Street apartment above the post office, where Winchester's most notable son, Leonard Wood, was born in October of 1860.

Leonard Wood's family left Winchester soon after his birth. Leonard spent his boyhood years on Cape Cod. He entered Harvard University in 1880 and became the house surgeon at Boston City Hospital upon graduation. Wood soon joined the military as a surgeon with the Geronimo Campaign in Arizona. He won the Medal of Honor before age 30 and remained in the military.

At the outbreak of the Spanish American War, Wood and his friend Teddy Roosevelt organized the First United States Volunteer Cavalry Regiment, better known as the Rough Riders. Together Wood and Roosevelt led the famous charge up San Juan Hill. Wood gained the rank of general and remained as governor of Cuba when the fighting ended. He cleaned up and civilized the city of Santiago with innovative health ordinances. General Wood also served as governor of the Philippines, was the originator of military training camps in the United States, and his name was placed in nomination at the Republican presidential convention in 1920. The nomination was eventually won by Warren G. Harding who went on to win the presidency.

Although he received three Distinguished Service medals, authored dozens of books and articles, and was awarded honorary doctorates by 15 universities, Winchester native Leonard Wood is best remembered for riding alongside Teddy Roosevelt as they led the charge of the Rough Riders up San Juan Hill.