In 1886, Cyrus G. Callison and his wife, Mary, of the Township of Linn in Warren County, sold and conveyed a strip of their farmland to the Chicago, St. Paul & Kansas City Railroad Company for the sum of $754.50. Two years later, Abner Frazier Callison, and his wife, Ollie F. Callison, along with the State of Iowa surveyed the original Plat of the Town of Cumming, Iowa.

The original survey consisted of two blocks, containing 24 lots, and was formally established as the City Of Cumming, Iowa on October 26, 1888. Three additions to the original Plat were added over the following five years, such that, by 1893, the Town of Cumming consisted of fourteen blocks and 125 lots. By 1908, the town had grown to include two general stores, three churches, a bank, a physician/drug store, one blacksmith, a barber shop, harness shop, feed mill, meat market, ice house, hardware/implement store, lumberyard and post office. There were approximately 20 -30 families in the town itself with numerous farmers supporting the local businesses.

One of the oldest structures in Cumming, the grain elevator, was built in the early 1900s and was later purchased by a group of farmers and turned into a farmers cooperative. Another familiar structure, a one-room school house so common in rural Iowa communities, represented the earliest educational facility in Cumming. It taught students from kindergarten through high school, and served the local community in many other ways. As the years went by, the Cumming School system was consolidated with the Norwalk School system to enhance the offerings available to the student body. By 1969, the school house was closed, only to reopen as Adam and Abby’s restaurant in the 1990s.

The past quarter century has seen a wide variety of changes; the general store, bank and gas stations have closed. The grain elevator went out of business, and the railroad, an important link for Cumming, removed its tracks. But rather than dwindle away, Cumming has seen a revitalization as the Des Moines Metropolitan region has grown.

The Chicago and Western Railroad’s old tracks were converted into one of the finest paved bike trails in the State of Iowa – The Great Western/Bill Riley Bike Trail. Numerous business have taken advantage of Cumming’s high quality of life by relocating in the area. And a number of high quality housing developments have been built, spurring the growth of this vibrant community.