Airport Inn began on Highway 81 (south of Fourth Street) in the mid 1940’s. The restaurant was known for the beer and chislic. Albert Krueger had purchased the barracks-style structures from the U.S. Army after the War. Krueger later sold the business to Ernie Stoebner, who ran the Airport Inn until 1961, when Barney and Marie Wrenn bought the business. In 1966 the name was changed to The Covered Wagon steakhouse and there was extensive remodeling done. The original barracks building eventually came down and the Wrenns rebuilt across Highway 81 in 1978. The Covered Wagon was in business until 1999.
Caseys General Store
In 1978 Casey’s General Store was built on the corner of Fifth and Cherry Street, opening in 1979. The store operated on Cherry Street for 34 years. In the fall of 2013 a new Casey’s General Store was built on Highway 81 and the old store on Cherry Street was closed.
Cornerstone Steakhouse
The Cornerstone Steakhouse was built in 1977 on Highway 81 and opened in 1978. The restaurant offered great food and featured gospel music, with room for over 300 people. The building later became Fellowship Harvest Community Church.
Dairy Queen
Dairy Queen started in the 1950’s on Main Street. In 1954 Leland Voth bought the business and moved it to Highway 81(now Ampride). Andrew Pollman bought Dairy Queen in 1956 and ran it until 1976. In 1977 Don Diede bought the business which became the Drive Inn. In 1990 Ampride bought the property and built a gas station
Fensels
In 1949 Wilmer Fensel purchased land north of town on Highway 81 where he built a house, planted lots of trees, and built chicken houses. In 1952 a twelve unit motel was built on Highway 81 called Fensel’s Motel. In 1954 Fensel’s Greenhouse was built and a year later a (50 by 24 foot) greenhouse was added. In 1964 a fire destroyed the Electrical Supply building on Cherry Street. The Hatchery moved to the country in 1964 and the rest of the business moved to Highway 81. In 1979 a fire destroyed the greenhouse, but the business survived. In 1981 a new florist building was constructed.
In 1965 Earl Gering and Ray Anderson purchased the Implement on Main Street and renamed it Freeman Implement Inc. “Case IH”. Ray Anderson sold his interest to Earl Gering in 1973. Earl’s son Brad Gering began managing Freeman Implement in 1979. Freeman Implement moved to Highway 81 in 1999.
Fred Haar
In 1972 the Fred Harr business was moved from Main Street to Highway 81. Fred Haar Co. was incorporated in 1978. In 2011 Fred Haar Company was sold to C&B Operations.
Freeman Coop
In the 1970’s Freeman Coop fertilizer plant moved to Highway 81. In 1971 the LP Gas business started and in 1976 the Coop purchased the Mobile One bulk plant. In 2004 the office moved from Main Street to Highway 81.
Kaufman Feed Service
Kaufman Milling Service was founded in 1956. Maurice Kaufman served the livestock and poultry producers in Freeman with a portable feed mill. In 1959 a second mill was purchased. In 1965 a warehouse was built on Highway 81. In 1969 a feed mill and grain storage were built on the south side of the warehouse. Kaufman Feed later became Central Farmers Feed Mill.
Mehlhaf Machine
Mehlhaf Machine & Manufacturing Co. started out on the Eugene Mehlhaf farm in 1973. In 1974 Charles Mehlhaf moved the business to Highway 81. In 1978 a 75 by 210 foot warehouse was built. Wildcat-Viper bought the company in 2002 and Vermeer purchased Wildcat in 2009.
Ralph's Feed
Ralph’s Feed and Farm Supply started in 1976 in a farm garage. In 1977 the business moved to Sixth Street (now Sioux Nation Ag). The business later moved to North County Road.
Rural Manufacturing
Rural Manufacturing started in 1968 on the Vernon Hofer and Joe D. Hofer farm west of Freeman. In 1973 Donovan Friesen joined the company. In 1976 Rural Manufacturing moved to Freeman and constructed a new building on Highway 81.
Silver Star Inn
In 1966 Toby and Erma Kapsch built a cafe on Fifth Street called Silver Star Inn (across from the Freeman Post Office south). In 1976 Ron Bennett bought the Silver Star Inn and moved it to Highway 81. The business was remodeled, expanded, and renamed Mr. B’s. In 1984 Myron Holzwarth bought the business and renamed it Corner Corral. It was bought by Gillas Stern in 1993, renovated, and became Papa’s restaurant opened. In 2004 Jim Rigo took over and ran the business until 2014. It has since become Prairie House, then the Chislic House.
Triple T
In 1977 Tiesen’s Trim & Upholstery Triple T was organized by: Gary, Orville, and Bert Tiesen. The business operated in a small shop on Highway 81 near the old Tiesen service station. Shortly after, a larger building was constructed for business, manufacturing saddles and western wear.
Wollman Pharmacy
In 1979 Dennis Wollman moved his pharmacy Wollman Drug from Main Street to Highway 81. Heritage Pharmacy & Wollman Merchandise Mart were built, operating until 2008/ The business was sold and Freeman Shopping Center opened.