Although there are records of people moving to the Winfred area in the 1870s, the town itself was not founded until about 1881. Among the early pioneers was a small but hardy contingent of Welsh, unusual in a county where a majority of the citizens had German, Norwegian, or Irish backgrounds.

There are at least two stories of how the town of Winfred received its name but the most commonly accepted one is that it was named after the daughter of banker Frank. W. Thaxter who owned the land on which the town was founded. With the county line marking the west side of the town, Winfred was the last Lake County stop for the Milwaukee railroad. The first train passed through on Christmas Day, 1881.

Winfred's post office was established on July 24, 1882. Other buildings soon included the depot, barbershop, dray line, confectionery, lumber company, two elevators, and a church.

By 1883, Winfred's population had risen to 150. That same year, two Englishmen purchased 1300 acres north of Winfred and started the LaBelle Ranch, a large horse breeding operation. They also founded and owned a bank in Winfred.

The 1890s were active years in Winfred. All the land in the area had been claimed but the population continued to grow as more people came to the town itself. In 1892, Winfred boasted two blacksmiths, a butcher, three coal dealers, four carpenters, a creamery and cheese factory, constable, two clerks, druggist, furniture dealer, three grain buyers, two general merchandise stores, hotel, livery, lumber dealer, minister, postmaster, railroad agent, stock buyer, teacher, and two well-drillers. The LaBelle Ranch, after experiencing financial trouble, was sold to Richard Westall, a wealthy man from Minnesota, and became a cattle ranch. Illness and extreme weather conditions took a toll on this enterprise as well.

Winfred's first schoolhouse was built in 1883. This building served many purposes, being used also as a meeting and election place, a church, and a place for play performances. A new schoolhouse was built in the 1890s. This second school was destroyed by a mysterious fire in 1919, “mysterious” because the school was heated using coal but an empty kerosene barrel was found in the ruins. Classes found temporary housing until a new, brick building was completed in 1922. This brick school was used for 43 years with the last graduates walking across the stage in 1965. Since then, area students have attended schools in Howard, Madison, and Ramona.

The Winfred Congregational Community Church was formally organized July 27, 1884 and met for three years in the schoolhouse. Rev. R.E. Matlock was also the first blacksmith in town. In 1889, the congregation was able to purchase the unfinished Episcopalian church in town. The bell from this wooden structure was later moved to a new brick structure erected in 1919. Both the bell and the building are still in use.

Despite its small size, Winfred has been home to four different newspapers. The first one was the Public Ledger. Winfred was also later the site of the Dispatch, the Witness, and the Pioneer.

The first electrical service came in 1915 on a line run from Howard, 11 miles away. Winfred's water system dates back to about 1918. Getting the voters' approval was the easy part. Completing the system was difficult; heavy rain delayed laying water mains but eventually the project was completed.

There were at least four doctors who made their homes in Winfred at one time or another. Drs. Monroe and Clapp were in town during the 1890s. Later J.F. Barthall and J.F. Willoughby served the town. Dr. Willoughby even ran a small hospital in Winfred.

Lake Winfred was formed when town leaders drained area sloughs. A pier was built and Lake Winfred became the area's destination for boating. This was the sight of a tragic accident on Dec. 3, 1915, when the local high school held a skating party. Two students, Vera Williams and Justice Hogance fell through a hole in the ice. Hogance was rescued but Williams drowned.

Baseball and basketball were popular among Winfred's citizens. The first baseball field was a buffalo wallow. Besides good baseball teams, Winfred was known for its basketball players. In 1931, Winfred had the distinction of having the county champions in both boys' and girls' basketball.

Winfred, like many other prairie towns, suffered at least one catastrophic fire. In 1909, a fire, perhaps started when a pipe ember fell into a sweeping compound that included an oily substance, raged through part of downtown. Fire departments from Winfred, Howard, and Canova couldn't contain the conflagration, which destroyed six buildings and caused $10,700 worth of damage. (Less than half of that was covered by insurance.)

Winfred's decline, like that of many prairie towns, began in the 1920s and was hastened by the Great Depression. The town may have gone the way of Franklin and Orland, also in Lake County, except for one thing. In 1958, a far-sighted thinker, A.H. Meyer, because of the sweet clover available in the area and the Soil Bank program, moved his beekeeping business from California to Winfred. The business of A.H. Meyer and Sons has gradually grown from one building to include most of the buildings still remaining on Winfred's main street. The old school building is now the company's headquarters. Its honey is highly prized and used all over the United States.

Besides A.H. Meyer and Sons, Winfred's businesses now only include the Post Office and Charlie Scholl's recycling business. Other area businesses are the Birds' Nest (a hunting preserve), Iron Wheel Salvage, and Jake's Corner (a convenience store).

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