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Character Backstory: Trip Filmore

Trip Filmore was born on January 22, 1844 in Boston, MA. His parents, James G. Filmore and Judith Ann Filmore, had founded the Boston Post a decade earlier and were well established in Boston’s social and political circles. Although young Trip spent most of his non-school hours helping around the newspaper offices, he often spent summers at a family property outside the city, where he learned to ride, respect and care for the family horses. This was more his passion than the business.

Although young Trip spent most of his non-school hours helping around the newspaper offices, he often spent summers at a family property outside the city…

Trip was 16 when the growing political unrest hit close to home with the failed attack at Harper’s Ferry in October of 1859. Shortly thereafter, it came out that several prominent Boston businessmen, including Charles G. Filmore, had been funneling money and supplies to John Brown, the architect of the raid. After Brown’s execution in December of 1859, rumors circulated among Boston’s elite that arrest orders from Washington were forthcoming, so in the spring of 1860 the Filmores sold their assets in the Boston Post and began making plans to move west to the mountains of Amabarino, where they intended to purchase a homestead and start over away from the inevitable conflict to come. Sixteen year old Trip was an idealist, supporting the goals of the the abolitionists, and did not want to “turn tail and run". That changed in March of 1860 when Judith was tragically killed in a carriage accident. On April 9, 1860 Charles and his son left by rail for Ambarino. Three days later US Marshals caught up with them in St. Louis, Missouri. Charles Filmore fought back and was shot and killed by the Marshals. Trip escaped in the commotion and found himself alone, destitute and helpless on the streets of an unfamiliar city.

Three days later US Marshals caught up with them in St. Louis, Missouri. Charles Filmore fought back and was shot and killed by the Marshals.

Falling back on his love for horses, Trip sought out stables for employment. He found the newly formed Pony Express which had just started service to Sacramento, CA a week earlier. Lying about his age, Trip signed up and became one of the service’s first riders. With his love of horses and experience on the family ranch, Trip turned out to be invaluable to the service, often riding multiple legs of the perilous run to Sacramento.

The Pony Express ended service in the fall of 1861. The attack on Fort Sumptner had started the Civil War a few months earlier, and Trip was conflicted on whether or not to return east to defend the Union. Still holding resentment against Washington for the death of his father, Trip chose instead to ride West, ending up in Sacramento, CA in the spring of 1862 at age 18. After working a few months in various jobs, Trip was contacted by his uncle, Joseph R. Filmore, who informed him that his father had purchased a homestead property in in New Austin prior to his death and that it was his if he wanted it. Trip again packs his meager belongings and heads out, slowly working his way East, finally arriving in Tumbleweed in the summer of 1863.

To be continued…