Shady Rest was established in 1921 with a clear and necessary purpose: to provide a recreational and cultural space for African Americans in an era when most country clubs, golf courses, and leisure venues were entirely closed to them. It offered golf, tennis, and horseback riding within an environment built on welcome rather than exclusion. The nine-hole golf course had been built in 1900 by the Westfield Country Club and was designed by David Smith Hunter, a Scottish golf professional. When Shady Rest took it over, the course became the site of some of the most significant moments in the history of Black American sport.

In 1931, John Shippen arrived at Shady Rest as the club's golf professional and groundskeeper. He would live there for more than thirty years, in an apartment on the third floor of the clubhouse. Shippen had been the first American professional golfer and, in 1896, the first African American to compete in the U.S. Open — an event his participation very nearly prevented from happening when white players threatened to boycott. He finished fifth. That history followed him to Shady Rest, where his presence gave the club a gravity no other venue could claim. On July 4 and 5, 1925, the club had hosted the first National Colored Golf Tournament — won by Harry Jackson, with Shippen finishing second — an event filmed on newsreel by Fox Films and significant enough to directly inspire the formation of the United Golfers Association the following year.

Tennis came to Shady Rest through a different door. In the 1940s and 1950s, six clay courts occupied what is now the ninth-hole green, and the club became a center for regional African American tennis — hosting the Eastern Open Championship in 1948, sanctioned by the American Tennis Association, and serving for a time as that organization's headquarters. Althea Gibson was a regular presence. She was known at Shady Rest as a tennis player — a coach and role model to younger members — before she picked up a golf club on the club's course. That interest grew into a professional golf career on the LPGA Tour, making Gibson one of the first women to compete professionally in two different major sports. Shady Rest can claim a role in that transformation.

The township of Scotch Plains acquired the property in 1938 and converted it to a public golf course in 1964, renaming it Scotch Hills Country Club. In 2021, the name was restored: Shady Rest Country Club. The following year, on July 7, 2022, the site was added to the National Register of Historic Places for its significance in entertainment, ethnic heritage, recreation, and social history from 1921 to 1964. In 2024 it was added to the New Jersey Black Heritage Trail. The clubhouse still stands — John Shippen's bedroom on the third floor, the Villa Casanova speakeasy in the basement — and the nonprofit Preserve Shady Rest is raising funds to restore those spaces and open a museum. The 2247-yard course still plays at par 33, largely as Hunter laid it out more than a century ago.