It is particularly known for its association during the 1920s and 1930s with the writer Alexander Woollcott, a member of the Algonquin Round Table, a group of literary figures.
The Rutland County Historical Society published an account of the event including a number of speeches and poems, and shortly thereafter a series of "colored books of Neshobe" were published, containing a variety of poems in honor of the island.
He built himself a large stone house, where he hosted a number of other members of the circle during the 1930s; Woollcott himself lived permanently on the island from 1938.
Some of the visitors to the island during Woollcott's time included Harpo Marx, Noël Coward, Ring Lardner, Thornton Wilder, Robert Benchley, Margaret Mitchell, Laurence Olivier, Helen Hayes, Vivien Leigh, Irving Berlin, and Walt Disney.
[5] A fictionalized account of life on Neshobe Island during this time forms the basis for Charles Brackett's 1934 novel Entirely Surrounded.