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Early settlers, chiefly from Connecticut and Massachusetts, came to this area around 1790. Mills and other small businesses were established in the early 1800s; a post office opened in 1820. The Great Western Turnpike, or Cherry Valley Turnpike, was completed this far in 1805 and gave the area early communication with Albany. It was a wood planked road running east and west across a large portion of New York State.

In these early years, the village was overshadowed by business activity in East Winfield, and the town meetings were held there. The four corners area in West Winfield was originally a bog hole, as was shown by the digging up of logs, slabs and tan bark four feet below the surface when the village water pipes eventually were laid.

The Village of Winfield obtained its name from the one given the Township. The town, which came into existence on April 17, 1816, was originally named "Scott" in honor of General Winfield Scott. When it was discovered that that name already was taken by another community, the name was changed to Winfield.

The present law office of Snyder and Quinn is a very early building (around 1800) and was once a blacksmith shop. The other early building to survive is also a law office belonging to Mr. Armstrong.

Not the earliest building on the site but the Fleet bank has resisted the trend of many banks to tear down and put up a modern building. The Feedstore was adapted by Wendell Saunders and now houses the West Winfield Dental Associates among several other businesses.

Bisby Memorial Hall was constructed by George Harvey Bisby (actually completed by his widow) and given as a gift to West Winfield in 1909. It's the West Winfield Library. The Agway store has become the Garland Restaurant.

Some of the old store fronts (with Italianate brackets) have remained stores adapting to modern necessities without tearing down the buildings. (Napa & Davis Hardware)

The Mount Markham Middle School was originally the West Winfield High School before consolidation of the three area school districts in 1969. The former West Winfield Elementary now houses all elementary children in the district and has become the Mt. Markham Elementary School. The Mt. Markham High School was built in 1974.