In the middle of the land was Indian Field which was the home for the Montaukett tribe.
The community was founded in 1860, and is named after the Montaukett Native Americans that briefly lived in Missouri.
Native Americans living on Long Island eventually became identified by European settlers by the place name in which they lived, such as the Montauk and the Shinnecock, artificially identifying the peoples separately and erroneously into "tribes", although they all shared the same culture and language.
Olivia Ward Bush Banks (May 23, 1869 – 1944) was an American author, poet and journalist of African-American and Montaukett Native American descent.
The trail was inspired by Stephen Talkhouse, a 19th-century Montaukett Indian famed for his 25-30 mile roundtrip walks from Montauk to East Hampton, New York and Sag Harbor, New York.