The Town of Cheswold began as a stop on the Pennsylvania Railroad known as Leipsic Station. Leipsic at the time had the largest cannery in the state, The Leipsic Canning Company. The railroad was completed in 1856. The primary landowner at that time was John S. Moore. He built a store on the property and was appointed Post Master. The new town was called Moorton after Mr. Moore. In 1888, the railroad asked the town to find another name because there was a Moorton, PA on the same line. The story goes that there was a contest to name the town. The winning entry, submitted by Minnie Dische, was “Cheswold”. The name came from combining “ches” for the chestnut trees that were common in the area at that time and “wold” meaning group of trees. The name officially became Cheswold on March 12, 1888.

The first mention of fire protection for the town was in 1901 when a basket factory in town caught fire. The Smyrna Times reported on the fire in an article titled “Cheswold Basket Mill Burned to the Ground”.Cheswold, June 12:-About twelve o’clock last Thursday morning the cry of fire and the ringing of bells aroused the people of Cheswold from their slumber. The fire proved to be the planning mill and basket works of Joseph M. Ford. Located as is, on the southwest side of the town a brisk southwest wind blowing at the time sent the high sparks from the light burning material on the central portion and for a time our people were much frightened. Horses were removed from stables to places of safety and household effects put in preparation for hasty removal. Had the nearest house, that of John Jewel, caught from the flames, the consensus of opinion seems to be the whole town would have been swept. Hard and risky work however, which with pride we can justly claim belongs to our Cheswold people, saved them from a general conflagration. A little fire apparatus called a “coffee mill” and laughed at because of its insignificant looks as a fire extinguisher, forced sufficient water through a hose to save the Jewell property and many others. The fire was also vigorously fought with other appliances.

Mr. Ford’s loss is variously placed at from $600 to $800. This includes 2700 half-barrel baskets, several thousand strawberry baskets, tools, machinery and the building, upon which there was no insurance. How the fire originated, occurring as it did in a storeroom for baskets forty feet from the engine and boiler on a bright moonlight night, is a great mystery. Mr. Ford is an honest, industrious worthy citizen and loses all by the fire. He has, we learn, decided to rebuild in another part of the town.

The next mention came in a 1925 convention booklet from the newly formed Delaware Volunteer Fireman’s Association. The history of the Robbins Hose Company No. 1 of Dover states: “…the town (of Dover) had a hook and ladder pump (which is now the property of Cheswold, Del.)…”.

In 1927 several men met regularly in C. H. Pearson’s store to discuss the need of forming a fire company in the town. Early in 1928 that need was proven when the home of Dan Turner caught fire. Friends and neighbors formed a bucket brigade until the Robbins Hose Company of Dover and the Clayton Fire Company arrived. Despite the effort, the home was destroyed. It is said that the only thing that saved the entire town from the fire was the easterly wind blowing that night.

Several meetings were held in 1928 on the subject of fire protection. The first official meeting of the Cheswold Volunteer Fire Company was held on February 2,1928 in the General Merchandise Store of C. H. Pearson. William S. Scarborough was elected as the first President and Willard D. Boyce the first Fire Chief. At the same meeting, William B. Harrington was elected Treasurer and John M. Ford was elected as Secretary. Approximately thirteen charter members were present at this first meeting, and they are believed to be Louis Anderson, Peter L. Barcus, Willard E. Barcus, Willard D. Boyce, Byron S. Creadick, John M. Ford, William B. Harrington, William W. Kerper, Denny R. Morris, William S. Scarborough, Edward Streets, N. Lee Remley, and Joseph E. Swain, Sr.