The Fundamental Orders adopted by Connecticut in 1639 directed would-be settlers, able to support a minister, to establish a settlement, build a Congregational church and farm the land. This is exactly what was done here in 1708. The original 24 proprietors received 7½ acre home lots drawn by lottery, with a 25th reserved for the minister. The lots were located up and down Main Street from a Common where a Meeting House was built. A close knit community of neighbors lived under the vigilant eye of minister Thomas Hauley, who also served as school master and town clerk. Each family was an individual survival unit—dwelling in a small home, farming its outlying fields, and husbanding a few farm animals on its lot.
One of the earliest entrepreneurs was Timothy Keeler, who had converted his home into a tavern in 1772. (It was fired upon by the British during the Battle of Ridgefield, April 27, 1777, and is today the Keeler Tavern Museum and History Center.) After the Revolutionary War, Keeler began to import goods from New York to resell in his tavern—everything from buttons to rum—and in 1783 Lt. Joshua King established the King and Dole store in a small building on the site of what is now the Aldrich Contemporary Art Museum.
The pace of commerce grew thereafter. By 1822, the town had hatters, tailors, weavers, carpenters, silversmiths, and 40 shoemakers. The 19th century also saw the birth of industry, beginning with carriage manufacturing. By 1830, the Resseguie and Olmstead carriage “manufactory,” called the Big Shop, had become a local landmark on the present site of the Congregational Church. Other 19th century manufacturers on south Main Street made candlesticks, furniture, and shirts. As they flourished, the owners began to enlarge their homes or build new ones and by 1850 the face of Main Street had completely changed.
Because Ridgefield lacked significant water power and was located off the main travel routes, it was unable to compete in the Industrial Revolution. The town lost population as its mills and shops closed. What kept Ridgefield alive after the Civil War was the arrival of prominent New Yorkers eager to summer in this quaint resort with its healthy air. By 1870, a new railroad spur began bringing these summer visitors to south Main’s Bailey Inn, Three Pines Boarding House, Ridgefield Inn, and Keeler Tavern (now the Resseguie Hotel). This fashionable crowd soon began to build mansion-sized vacation retreats on south Main Street and elsewhere in town.
By 1890 the Common and the old Congregational Church were gone, but very little else had changed since earlier in the century. In 1966, the area was designated a state and local Historic District and in 1984 a National Historic District. It is administered by the Ridgefield Historic District Commission.
Since its founding, Ridgefield has inherited a rich 300 year history, that includes such personalities as Benedict Arnold who fought here, Frederick Remington who sculpted here, J. Alden Weir who painted here, and Eugene O’Neill who wrote here.