Wentworth, the first Lake County town through which a railroad came, was named by Rinaldo Wentworth, who owned the land on which the town was founded, in honor of his father. Other names that had been under consideration were Milwaukee, Wicklow, Winton, and Alto.

The first train reached the fledgling town in October 1880. One of the first businesses in Wentworth was George Weiss's mercantile. Other businesses quickly followed and included a bootmaker, druggist, more general stores, newspaper office, a hardware store, hotels, a restaurant, newspaper, livery, millinery, lumber yard, and, of course, a saloon and a pool hall.

The first school in the area was the Wicklow School, built in 1879 on land owned by Philip Zimmermann southwest of the present town. After Wentworth's founding, lessons were first held in a schoolhouse moved in from west of town, and, then later, in another building until a larger school was built in late 1885. The new school bell, weighing 1100 pounds arrived on January 5, 1886, just in time for the winter session.

1886 also marked the founding of a parochial school affiliated with St. Peter's Lutheran Church in Wentworth. Lessons here were held in German until World War I, when anti-German sentiment closed the school for a while. It later reopened but lessons were taught in English from then until its closing in 1937.

The public school graduated its first four-year high school class in 1914 and its last in 1949. Wentworth retained a school for the first eight grades until 1965, when the school closed and became a part of the Chester district.

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Wentworth has been home to three churches-St. Peter's Lutheran, Protestant Episcopal, and First Presbyterian-all founded during the early to mid 1880s.The first services of St. Peter's were held in a private home and a vacant storefront until the church was completed in 1884. The Protestant Episcopal Church was built in 1886 but, due to lack of support, closed and the building was sold to St. Peter's Lutheran in 1891. By 1904, St. Peter's outgrew that building so another building, still in use, was constructed. First Presbyterian's original building wasn't completed until 1900 although services had been held elsewhere as early as 1882. This building was destroyed by fire in the fall of 1913. Its replacement has been in use since 1914.

For a small town, Wentworth has an impressive history of newspaper publication. The Dakota Letter was printed from 1881 until 1888. The Wentworth Bond ran from 1883 to 1888. These were followed by The Wentworth Enterprise which ran for 23 years, from 1900 until 1923. The Lake County News lasted from 1918 until 1932. Wentworth's last newspaper, The Wentworth Progress, ran from 1924 until 1952. A German-language newspaper was printed in Wentworth until World War I, when, like the parochial school, it was forced to close.

Wentworth had telephone service before it had a water system. The first telephone lines were installed in December 1904. Connections were poor but early store owner C.H. Weiss vividly recalled hearing the news that President McKinley had been shot.

Wentworth's water works system wasn't completed until 1909 although a town well was dug in December 1898. Since 1976, Wentworth has been a part of the Big Sioux Water System.

Electrical service made its way to Wentworth in 1917. Once seven farmers between Colman and Wentworth agreed to sign up for service, the Dakota Light and Power Company of Flandreau agreed to run lines from Colman to Wentworth. The electric streetlights came on for the first time in February 1917.

Many physicians served the Wentworth area. Dr. A.E. Clough, Lake County's first doctor, who served a large area, was followed by Dr. J.E.Schneider, who was the first resident doctor. Dr. A.D. Hard of Wentworth had the distinction in 1899 of having the first automobile west of the Mississippi River, a Stanley Standard Stanhope Model #1. (He only had it three months before it caught fire, burning down the barn it was stored in.) Other doctors over the years were T.Y Stevenson, A.H. Rogers, J. Young, E.W. Goldman, Dr. Gibson, G.L. Hickman, C.N. Brooks, W.R. Scott, and V.A. Mokler.

Dr. Taylor was the first resident dentist. Another dentist, Bruno Harms came to Wentworth and worked over the weekends.

Veterinarians over the years included A.P. Hull, O.S. Merager, and J.A. Struble.

Many of Wentworth's early citizens, like the Zimmermann's, the Rosenows, and the Glaettlis, were well-educated and fairly well-to-do. They organized literary and debating societies, dances, the Turner Verein (an association of turners, or gymnasts), and Lyceum meetings. (A lyceum course featured musical programs, readings, and lectures.) A Fourth of July picnic was one of the year's big events. Other events were an agricultural fair and, later, Corn Days. The Wentworth Cornet Band provided music for dances, picnics, and other occasions.

Wentworth, like many other South Dakota towns, fielded some well-respected baseball teams. A game between Wentworth and Colman during the Fourth of July picnic in 1912 was hotly contested and was called off as a tie. The "Little Norway" team was organized about 1915 and was known to play the Wentworth Whiz Bangs in George Strang's pasture. In 1953, the Wentworth Lutheran's Men's team lost the state title by one run.

The Wentworth of today is similar to many South Dakota towns, having gone through a decline but still holding on. Businesses still located in town include the Post Office, a construction company, a repair shop, a bar, and a body shop. The surrounding area is home to an ethanol plant, two lakeside resorts, a marina, a realtor, and a cleaning service as well as other home-based business.