When Aiken was founded, in 1835, it was a stop on the longest regularly scheduled railway line in the country, from Charleston to Hamburg, South Carolina. Wealthy planters from Charleston built summerhouses in Aiken. The town, being situated in the hilly country between the Savannah and Edisto rivers, was mostly free of the heat and malaria that plagued the low country. Sherman did not burn Aiken—his army was routed on the outskirts by Major General Joe Wheeler's ragged militia, a storied event that is re-enacted each year, in late February.
After the war, Aiken developed a reputation as a health resort, which is what brought a sickly little girl named Louise Eustis (known as Loulie) to town in 1877. Loulie's parents had supported the Confederacy; during the war her father, George Eustis, a congressman from New Orleans, served in the Confederate embassy in Paris. Loulie's mother and father both died abroad shortly after the war, and the young orphan's grandfather, W. W. Corcoran, whose immense fortune was based on banking, arranged for her to be raised in New Orleans by her aunt, Celestine, a prominent social figure there. When Loulie showed signs of consumption (which is what killed her father), Tante, as she called Celestine, took her to Aiken for the healthful air.
Loulie fell in love with Aiken, learned to ride, and returned each year for an extended stay. Always fearless and unconventional, she eschewed the demure sidesaddle riding fashion of the day and became the first woman of her class to insist on riding astride. When she was 18, her grandfather Corcoran settled a fortune on her, and Loulie was brought to New York City to make her debut. There she met young Tommy Hitchcock, the polo-playing scion of a New York banking family, whom she married in 1891.
Hitchcock and his neighbors on the north shore of Long Island were looking for a place to ride, hunt, and play polo during the winter months, and Loulie insisted on showing Aiken to her new husband. Hitchcock realized that the town was exactly what he was looking for. The couple bought a house from the Legares, a prominent low-country family—beginning the unique marriage of Southern and Northern notions of aristocracy that is part of Aiken's style—and they recruited some of their New York friends to come down South with them. William Whitney bought many of the racing and polo facilities, as well as a residence on Easy Street called Joye Cottage—an all-white, Neoclassical pleasure palace that in recent years was restored by the authors Gregory White Smith and Steve Naifeh, who won the Pulitzer Prize for their biography of Jackson Pollock; the house became the subject of their book On a Street Called Easy, in a Cottage Called Joye.
The ideal of the Winter Colony was to play three sports a day—polo in the morning, followed by a game of golf, and then a hunt late in the day, preferably after dark, when the riding was at its most hazardous. Both the men and the women, having inherited extraordinarily large fortunes from their daring and rapacious ancestors, seemed determined to amuse themselves in a life-threatening manner, to prove that leisure was just as challenging as work. Too rich to work, but too active and restless to sit still, they developed in Aiken a hectic style of leisure that became a preppy convention, and that Americans could see in the Kennebunkport vacations of George Bush the first—especially those high-speed golf outings.
For relaxation, the colonists shot quail, played bridge, and entertained one another with lavish horse-drawn picnics catered by a local German family named Willcox. They built squash courts in their houses, and created their own court tennis facility (one of the few in the country) and the Palmetto Golf Club (Stanford White designed the clubhouse). However, in its choice of sports the Winter Colony seems to have reflected the conviction Thomas Jefferson once put into a letter to a friend, that "games played with the ball...stamp no character on the mind." When the winter ended, they packed up their playthings and took their private railcars back home to the hunts and polo fields of Long Island.