Chester was the first Lake County town that was the result of the expansion of the South Dakota Central Railway. There are records of people living in the area as early as the 1870s but the town itself was not founded until 1905 when people of the township were told a town would be built if they gave a bonus to the S.D.C.R.R. Otherwise, the railroad said, they would build farther west. Told the railroad would come through before the end of 1905 or they would get their money back, area farmers, spearheaded by Louis Krumm and Lewis Spawn, quickly came up with the money. The railway kept its promise; the first train arrived in Chester on September 11, 1905.

According to old timers, a saloon was the first building in Chester. This was operated by Benny DeBelts who was said to be a little person who could barely see over his counter. Other important businesses of the early town were lumber yards, a general store, a restaurant, a hotel, a drugstore, and a banker who operated out of a suitcase as he sat on an apple crate.

The first homes were four cottages constructed by the firm of Kirby and Boller for the railroad. Three of these houses are still standing.

Within three years, Chester had two elevators, two churches, two saloons, three general stores, a combination hardware-furniture-implement-harness shop, drugstore, livery service, doctor's office, barbershop, meat market, blacksmith shop, and shoe shop. A promotional booklet from the same year said the town was still looking for a jeweler-watchmaker, a creamery, a flour mill, and a photographer.

Chester had a school as early as 1877. The area had at least five rural schools by the turn of the century. The largest school once had 61 students and one teacher. In 1910, a larger, two-room school house was built in town. Two years later, two more rooms were added. A large, brick building replaced this in 1921. In 1949, the Wentworth school combined with Chester and Franklin consolidated with Chester in 1965. A 1967 fire destroyed this building two days after the new school year began. The current building dates back to 1970.

Chester is the site of two churches, the Methodist Church and St. John's Lutheran. The Methodist Church had been moved in from Prospect, two miles west, in 1907. Also in 1907, the German Lutheran Church, now known as St. John's, was erected. The present Methodist church was built in 1918 and the Lutheran one in 1948.

It is not known when Chester's telephones were installed but the switchboard was first in Roney's drugstore. Call times were limited and long-distance calls were only for dire emergencies. Chester's current water and sewer system dates from 1967. (The ground-breaking for this system was just nine days before the disastrous school fire.)

The area north of Chester along Brant Lake was also a busy business area. Lewis Spawn, one of Chester's founders, owned a cement block factory. These blocks were used in several area buildings, including two homes still standing in Chester. Spawn's Resort, started by Earl and Josephine Spawn, was the site for rental cottages, rental boats, a skating rink-dance hall, a bath house, a mini-golf course, and a tennis court. Also near Brant Lake, on land owned by the Spawn family for almost a century, is an ancient burial mound. An excavation in 1966 dated two of the three pits here to be about 1000 years old.

In 1916, Chester became the home of Dr. L.E. Jordan, a young medical graduate. For almost 34 years, "Doc" Jordan, Chester's only resident physician, treated injuries and epidemics and delivered many of the areas babies.

Chester has also been an active sports venue. The school basketball team dates back to at least 1912. This early team rode railway flatcars to games and would walk back to Chester afterwards.

Softball was also a popular area sport and Chester hosted South Dakota's first two 16" softball tournaments in 1965 and 1966. No gloves were allowed and one game was still being played at 3 a.m.!

Chester's early attractions included a golf course located about a mile and a half south of town. A popcorn machine was also a thriving business for many young people over the years. Movies were shown outdoors on a screen at the ballpark or on the side of a building until Harris Benson opened the Royal Theater around 1950. None of these are still in existence but played an active role in the social life of this small town.

Chester has had its share of disasters, including fires that destroyed a number of businesses. In August, 1967, the school was also destroyed by fire. Chester's worst disaster was the tornado that struck August 9, 1992. This F-2 twister, which followed the railroad tracks, destroyed the elevator, community center, lumberyard, fertilizer plant, and other buildings, including a home. Miraculously, during the tornado, no one was injured, not even the four firemen clinging to the refrigerator in the community center.

A flood the next summer cut off most access to the town. The only dry road into Chester was the one on the southeast side of town.

Over a century after its founding, Chester still has a variety of businesses. Chester has had a post office since its founding. A barber shop has operated in the same building (moved in from Seranac) since 1911. The Benson family has operated a hardware store in Chester since 1926. Other current businesses include a farm service, trucking concern, gas station-garage, two construction companies, café, convenience store, nursery, two day cares, two hair stylists, painter, interior decorator, pool hall, bar and grill, promotions business, dog breeder, gardeners, and rental toilet business.

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