Chester Inn

Chester Through the Mid-1800s

With the Chester established by Joseph C. Wright, the home and grounds that we know and love today began to take shape throughout the 1840s.

Mr. Wright began to plant many specimens of trees and shrubs throughout the property over the next several decades, most of which remain on the arboretum grounds today. As was fitting of his British heritage, he introduced stands of English boxwood, which grow very slowly (less than an inch each year).

These boughs are in great demand during the holiday season and are still trimmed each year by distributors who then send Chester boxwood off to florists throughout the country.

In 1851, Mr. Wright added a stable and sold Chester to John H. Coleman, but continued to live there as a caretaker. Coleman sold the property in 1853 to George Walton Dillard for $2,375. The price of sale continued to fluctuate and the property changed hands several times, actually once moving from the seller to the buyer and back again. In total, the Dillard family lived on the property for over 100 years.

The Dillards used the house as a country retreat from their lives in Richmond. During their time at Chester, many additions and changes were made to the home and grounds. During the early years of the Civil War, Chester was known as one of the “party houses” in a town surging with prosperity. There were picnics, dinner parties, quilting bees, teas, dances, and even ice skating on the pond that still remains on the property.

In 1865, Scottsville saw the full brunt of the Civil War. Sheridan and Union troops raided the town while Major Hill was occupying Chester, recovering from an amputated arm. Colonel George Custer and Sheridan came to visit and decided not to arrest who they thought was a “dying man.” They left Chester alone, Major Hill recovered, and the house remained unscathed.