The town of Bedford was founded on December 23, 1680, when 22 Puritans from Stamford, Connecticut, purchased a tract of land three miles square known as the "Hopp Ground" from Chief Katonah and several other Native Americans for coats, blankets, wampum and cloth.

[7] Bedford was made a part of Connecticut in 1697 when a patent fixed the boundaries as a six-mile square.

Only when King William III of England issued a royal decree in 1700 settling a boundary dispute did Bedford become part of New York.

[10] After the Revolution, Bedford was made one of two seats of county government, alternating with White Plains, until 1870.

Westchester County's oldest government building is the Court House in Bedford village, which was built in 1787 and renovated in the 1960s.

The northern portion of the Byram Lake Reservoir is situated on the southern limits of the town.

The river originates in a series of small ponds in Armonk and flows north into the town of Bedford.

[13] In the hamlet of Katonah are two national historic landmarks, which are "Stepping Stones - Historic Home of Bill & Lois Wilson" (home of the Alcoholics Anonymous co-founders; "Bill W.", who died in 1971 and "Lois W.", who died in 1988) and "John Jay Homestead", home of one of the United States Founding Fathers and first Chief Justice of the United States Supreme Court.

There is a small graveyard dating back to the founding of the town; the old one-room stone schoolhouse; and a few colonial-era houses, still lived in, which are kept painted white with black or green shutters.

The Record-Review, a weekly newspaper, reports on local issues in Bedford and Pound Ridge.