Archeological excavations have uncovered evidence that people have been living in the area since the Paleo period (10,500-8000 BCE). By the middle and late Archaic period (6000-1700 BCE) groups became territorial as populations grew and became more sedentary.
The Wiechquaeskeck tribe inhabited the area that is now The Bronx, Westchester County and western Fairfield County. The Wiechquaeskeck were Alqonquian Woodland Indians who spoke the Munsee dialect, which was spoken by tribes ranging from the mid-Hudson Valley to the Delaware River. This group of Munsee speaking tribes are called Lenape. They are also referred to as Delaware.
In 1701 the last of the Wiechquaeskeck were forced to leave their lands in the Stamford area and relocate to a native village called Ramapoo located in what is now the town of Ridgefield. The word is Lenape in origin and is said to mean "a rocky place". The village included members of the Tankiteke and Wiechquaeskeck tribes. The sakima (or chief) of the village and the surrounding area was Katonah (also spelled Catoonah). He was the sakima for all Wiechquaeskeck in the Greenwich, Stamford and Bedford areas.
In 1708 a group of 24 families of English settlers from Norwalk petitioned the Connecticut General Assembly for the land where the village stood. The group of settlers paid 100 pounds (roughly $400,000 in today's dollars).for 20,000 acres of land. On September 30, 1708 a deed transferring the land to the "Proprietors of Ridgefield" was signed by Catoonah, Waspahchain, Wawkamawwee, Wooquacomick, Naraneka, Tawpornick, Cawwehorin and Gootquas.
"Chief Katonah was the son of Onox and the grandson of Ponus. Catonah had a brother named Onox. Catonah was the successor to Powahay, also a grandson of Ponus. Catonah's daughter married Sam Mohawk alias Chicken Warrups. Legend has it that Chief Katonah died of grief after his wife, Cantitoe, sometimes known as Mustato and their son, Papiag, were killed by lightning. Chief Katonah is said to be buried with his wife and son in Katonah's Wood, off New York Route 22. The Chief is said to be buried beneath a giant boulder, and his wife and son are buried beneath two smaller immediately adjacent boulders."
Chief Katonah's mark
Sept. 30, 1708 – “Catoonah, sachem of Ramapoo Indians and Associates within her Majesties province of New York in America,” sells the first settlers an estimated 20,000 acres. The price is 100 pounds.
March 18, 1715 – The Proprietors pay four pounds to “Tackora, alias Oreneca, Indian,” for land in the Scotland and Ridgebury areas, including the outlet of Lake Mamanasco.
Nov. 22, 1721 – The Proprietors complete the third purchase from the Indians, paying six pounds for a sizable tract on West Mountain bordering Round Pond and including land now in Lewisboro, N.Y., running north through the area around Ridgefield High School and Mopus Bridge Road and east to Barlow Mountain and North Street.
July 4, 1727 – The Proprietors complete the fourth purchase from the Indians, including Taporneck, Wett Hams, Moses, Richard and Samm and paying 18 pounds, two guns, and three bottles of rum. The land is now in Lewisboro and North Salem.
March 7, 1729 – In the fifth purchase from the Indians, the Proprietors acquire more land now in New York State, from seven Indians, including Taporneck, Wett Hams, Crow, Moses, and Sam.
April 10, 1729 – The Proprietors complete the sixth purchase from the Indians, a sizable tract that includes much of today’s Ridgebury. The deed is signed by eight Indians, including Ah Topper, Mokens, Waw Sachim, Jacob Turkey and Captain Jacob Turkey.
Feb. 28, 1738 – The Proprietors complete the seventh purchase from the Indians, including land now in New York.
Dec. 19, 1739 – The town makes the last of eight purchases of Indian lands, a huge tract that runs from Ridgebury to the New Fairfield line. Most of it was ceded to Danbury in 1846. The deed was signed by Betty, Jacob Turkey and Mokquaroose.
Image from "The First Traders on Wall Street" by John Alexander Buckland
Ridgefield and Fairfield County’s Native Populations – a lecture series by the Ridgefield Historical Society
Episode One: The Founding of Ridgefield
Episode Two: The Ramapo Village Indians
Episode Four: King Phillips War
Connecticut's Indigenous Peoples by 
The First Traders on Wall Street by