"It has been truly said of Hampton that it expresses more grandeur than any other place in America," wrote Henry Winthrop Sargent in 1859. It was the first three Masters of Hampton who were responsible for the reputation it enjoyed for decades. Captain Charles Ridgely, known as "the Builder" of one of the largest Georgian mansions in the country, his nephew and heir, Charles Carnan Ridgely "the Governor," whose successes in business and politics brought attention from prominent circles; and the Governor's son John Ridgely who, with his wife Eliza, purchased elegant furnishings from abroad and nurtured the gardens and grounds into the serene vistas they remain today.
Revolutionary leader Charles Carroll described a party at Hampton in the early 1800s for which 300 invitations were issued. Such events were staged not only for entertainment but to cement business and political ties. Hampton mansion was ideal for such festivities: its Great Hall measures 51 by 21 feet and could seat more than 50 dinner guests. An English visitor noted in 1805 that Charles Carnan Ridgely was said to "keep the best table in America."
Upon the death of his uncle, Charles Ridgely Carnan took Ridgely as his surname, inherited most of Hampton's property and lands, and proceeded to consolidate the Ridgely fortune. Like his uncle, Ridgely had a townhouse in Baltimore and spent only part of the year at Hampton. In 1908 he was remembered as "the typical aristocrat of his day. He had the fortune that enabled him to live like a prince, and he also had the inclination."
Hampton was famous for horses. Breeding and racing thoroughbreds began in the late 1700s, before the mansion was built. By 1805, Charles Carnan Ridgely had constructed the first stone stable and laid out a racecourse on his property. Ridgely, owner of some of the finest thoroughbreds in America, was in large part responsible for Maryland's reputation as the center of American racing in the early 19th century. A silver trophy, presented to the Governor in 1805, depicts one of his favorite thoroughbreds, Post Boy. Even while Hampton declined after the Civil War, the Ridgely's continued racing, breeding, and fox hunting well into the 20th century.