In 1946, Carl Schaefer purchased 150 acres of land to develop a golf course on the rolling hills off of Pleasant View Road in Middleton. He laid out the first nine-hole course on 75 acres and saved 60 acres for the second nine-hole course. He began building the clubhouse in 1954. On May 30, 1958 the clubhouse and first nine holes were opened to the public. He continued building the second nine holes which opened in 1965. Carl hired Jerry Kessenich to be the greens-keeper. In 1969, the old first nine was turned into the par 3 course and driving range and a brand new 18-hole course was built covering about 200 acres. On August 15, 1970 the new 18-hole course was opened to the public.
CUNA Mutual Investment Corp. later acquired the Pleasant View property in 1978 as an alternate home office site to accommodate expansion needs. When CUNA was able to acquire expansion space across from their Mineral Point Road location, they continued to hold the Pleasant View property as an investment. The course was managed by John Born.
The city of Middleton paid $7.7 million for the 190-acre golf course in 1995 as part of its purchase of 308 acres on its southwest border from CUNA Mutual Group. The stated goal at the time was to protect the area from development but the city had been weighing offers for some of the land as it seeked to retire remaining debt from the purchase. In 2003, the new 27-hole course opened and in 2007, the new clubhouse opened. Ted Donker managed the course until 2015 when Jeremy Cabalka took over. In 2023, due to the Pleasant View Road expansion project, course renovations occurred and will open in 2024.