In 1950 Calvin Kleinsasser started Kleinsasser Plumbing & Heating on Sixth Street in a 24 x 24 foot horse barn. In 1960 a 54 x 42 foot Quonset was constructed over the building. In 1975 a 40 x 60 foot addition was added. From 1965 to 1978 there were 850 heat pumps were installed.
Pine Hill Printery
In 1960 Gering Brothers (John and Henry) brought their printing business (Pine Hill Printery) to Freeman. Pine Hill Printery moved into the Roller Rink on the corner of Sixth and Relanto Street. Pine Hill Printery operated from 1940 until 1991 and the business was sold. Pine Hill Printery became Pine Hill Press and moved to Sioux Falls. Smidt Furniture operated in the building in until a fire in 1994.
Willow Inn
In the 1930’s there were a few businesses outside of town, east of city limits. Jones Taven was just east of (now Printed Impressions) as well as a pool hall. After Charley Fliginger retired from farming in 1970, he started a body shop on Sixth Street called Willow Inn where he repairing damaged vehicles for resale. A 50 x 80 foot pole building was constructed and cars were purchased from an auto salvage in Missouri Valley, IA. Charley expanded the business in 1979 and operated until the late 1990’s. The building was sold to Phillip Svartoien and became Printed Impressions.
Dickman Service Station
In the early 1900’s John Gross operated a Nusery on Sixth Street (lot 6 & 7 across from now East River Furniture). In 1930 Christian P. Dickman moved to Sixth Street and bought the property from John Gross. In 1934 Christian bought two Warrior gas pumps and started Dickman Service Station. The building moved in the 1950’s.
Smidt Appliance
In 1964 Harry Lee Smidt started Smidt Appliance at 371 S Main Street. The business later moved to Menno. In 1993 the business moved back to Freeman in the Pine Hill Printery building. After a fire in 1994 Smidt Furniture was rebuilt on 911 Sixth Street in 1995. The warehouse was added on in 2000. The business later became East River Furniture.
Sioux Nation Ag
Freeman Vet Clinic started in 1992 at Dr. Hofer’s building on Main Street. The Vet Clinic moved to Sixth Street in 1995. In 2012 the company became Sioux Nation Ag.
Huber Motor
In 1950 Jack Wipf Jr. built a round-topped building west of Freedom Garage (on Sixth Street) for Jack’s Implement. In 1964 Alvin Huber purchased land on Highway 81 for a future business. In 1974 Orville and Reno Huber bought Jack Wipf’s property on Sixth Street and moved Huber Motor from Main Street.