The town of Jessie was founded when the railroad extension from Cooperstown to McHenry was built in 1899. A post office named "Jess" had been established at the home of W. T. McCullough at Lake Jessie in 1884 with Mr. McCullough as postmaster. But with the building of the railroad to the new town of Jessie the post office was moved to Jessie where Wilson J. Humimer became postmaster.
The townsite of Jessie was purchased by the Northern Pacific Railroad from Frank Pfiefer but was resold to Mr. and Mrs. J. E. Mellem who planned to name the town "Mellenville" but early settlers persuaded them to call it Jessie. Lake Jessie had been named by Lt. John C. Fremont of the Nicollet-Fremont expedition of 1939 in honor of his fiance, Jessie Benton, whom he married in 1841.
The "Couriers" of 1899 mention the start of various business places that year: an elevator for Olson and Cox, the Cull River Company, the general store for J. E. Laffin, and a hardware store for Anton Enger. Later on a bank was built which was operated by Harry St. John as cashier. Nels O. Haugen was an early day hardware store operator and postmaster. Reynold Hovel now runs the Laffin store but for several years it was operated by C. P. Dahl. Mrs. Dahl was postmaster for 23 years.
PUPILS AT JESSIE'S FIRST SCHOOL
First row (seated) Rosemary Rogney, Earl Ressler, Irving Thorn, Mary Hovel Evangeline Rogney, George McCullough and (standing) Harold Dalton; second row: Garry Rickford, Lawrence Ressler, Wallace McCullough, Muriel Thorn and Fritz Trost; third row: Irene Ressler, Sophia Trost, Lina Hovel, Alvina Zimprich and Evelyn Dalton; back row: Eva Wild, Edna Wild and Pearl Dahl Nelson, teacher.
Source: Cooperstown Diamond Jubilee 1882-1957 Page 53