When Bedford was bought from the Native Americans in 1680, the Church of England had only one settled clergyman in all the Northern Colonies - the chaplain to the garrison of New York City. Bedford, like nearly all the early New England settlements, was Puritan, and the original twenty-four settlers had moved inland from the coastal town of Stamford.
It wasn't until 1704 that Bedford residents banded together to organize what would later become the parish of St. Matthew's. Services in Bedford were held at a meeting house or parishioners would travel to Mount Kisco for worship. Missionaries serving the community were industrious but often short-lived, and in the years between the founding of the Bedford Church and the American Revolution, thirteen clergy had come and gone.
In 1759, Mr. St. George Talbot made a bequest of six hundred pounds "for the use of promoting true religion in North Castle and Bedford." Construction of what was originally known as "The Brick Church" was begun in 1807 and completed in 1809. On October 17, 1810, St. Matthew's Episcopal Church was officially consecrated.
The present Parish House was constructed in 1946 and enlarged in 1960 and 1999. It houses the church offices, library, Fellowship Room and church school classrooms. It is dedicated as a memorial to those who died in World War II and in honor of all who served.
The Churchyard, the burial ground for St. Matthew's, was officially established in the northwest corner of the property in 1812, and has been extended several times toward the eastern edge of the glebe, bordered by Beaver Dam Creek. In 2004, a new memorial garden was built and consecrated in the Churchyard.
Nearby, in a towering grove of hemlock trees, is the Chapel in the Woods, built in 1939. This rustic outdoor chapel, with its rough-hewn benches and an altar made of a fieldstone slab, is used at certain times during the summer. The 25 acre Ketchum Preserve was acquired, at no cost, by St. Matthew's from The Nature Conservancy in 2003 and annexed to the existing Glebe.
On a triangle of church-owned land across from the Rectory, the Bedford Cross was erected in 1936 as a wayside cross that would invite the prayers of those who passed by.
A multi-year celebration of St. Matthew's bicentennial was held between 2005 and 2010. It culminated in a 200th anniversary of the consecration of the sanctuary in 2010.