In the Wolcott's early years, it was popular with travelers, although it also rented rooms to permanent residents. Among the Wolcott's most famous residents were dancer Isadora Duncan, tobacco magnate James Buchanan Duke, heiress Doris Duke, writers Edith Wharton and Mark Twain, and theatrical producer Henry Miller.
During its early days, the Wolcott was a popular destination for travelers, but also provided lodging to permanent residents. Notable figures who resided at the Wolcott included dancer Isadora Duncan, tobacco magnate James Buchanan Duke, heiress Doris Duke, writers Edith Wharton and Mark Twain, and theatrical producer Henry Miller.