Koshkonong was named for its numerous sinkhole ponds and small lakes that reminded the construction supervisor of its original railroad's favorite duck hunting spot in Wisconsin, Lake Koshkonong, which was named after wild rice by Native Americans. The sinkholes are part of a karst system and serve as recharge for Mammoth Spring, 10 miles south in Mammoth Spring, Arkansas.
Koshkonong was once part of southern Missouri's fruitbelt that sprung up along the railroads in the area. Due to thousands of acres of large peach orchards and numerous packing plants, Koshkonong once billed itself as the "Peach Capitol of the World". The orchards' trees eventually succumbed to disease and non-productivity, and have since been replaced with pasture land.
Although Koshkonong's glory days have since faded, it still has a public K-12 school, post office, public library, senior center, volunteer fire department, historic museum, and several churches. Businesses in operation consist of a convenience store/truckstop, small meat processing plant, wholesale outlet, and feed store outside of town. A sizable hardwood flooring mill, located at Koshkonong, is one of the largest employers in Oregon County.
Beef cattle are raised on numerous cow/calf operations throughout the countryside. Meat goats are becoming more popular and an auction market specializing in goats and exotics has been built at nearby Brandsville, Missouri for this purpose.
Recreational and hunting opportunities include Cover Prairie Conservation Area, a former hog farm renaturalized for preservation of bobwhite quail and predatory raptors and donated to the Missouri Department of Conservation. Warm Fork Conservation Area is a MDC property offering hunting, hiking, and the springfed Warm Fork Creek. Grand Gulf State Park is a popular state park operated by Missouri DNR and owned by the L-A-D Foundation. Grand Gulf is a collapsed cavern and also recharges Mammoth Spring. Hiking and picnicking are popular at Grand Gulf.