Hillendale Country Club, the Old Club as some refer to it, was started in 1923 at the intersection of Hillen Road and Taylor Avenue. It began as a private enterprise by the Preston Realty Company built from the Old Hillen Estate, the home of the early Mayors of Baltimore. The old mansion, built in 1793, became the clubhouse, the stone barn was the locker room, and the pre-Civil War slave's quarters were used as the Golf Pro Shop. The club functioned through numerous trials and tribulationse. This led to selling and reselling to private individuals with Hillendale Country Club being leased without interruption to the membership in 1953. At one point during WWII, the club had been affected to the point of bankruptcy and the majority of the Board voted to discontinue the club.
Many members got together and with, the "Hillendale Spirit" and "Never Say Die" attitudes, they began working to solve the immediate problems. There were only 145 golf members who, with voluntary contributions and an aggressive new membership program, brought the club back to solid health. In 1952 Hillendale was informed that the club lease would be cancelled in 1954. There was much scrambling over the 17-month period as land was purchased, an architect was hired, a clubhouse was designed, a pool complex was installed and the staff was hired.
On July 9, 1954, the Clubhouse was officially opened and the next day the first tee shot was struck. In the 1970's, George Fazio was hired and fairways bunkers were added, along with changes to the greens complexes. In the 1980's, Tom Clark of Ault and Clark, made improvements to the driving range. Bob Cupp made golf course changes such as the redesign of the 13th hole and the connection ponds on the 5th and 6th holes.
Then came the 1990's. In both 1992 and 1993 the greens were unfortunately lost. If that wasn't enough, on August 19, 1993, the clubhouse tragically burned to the ground. And so a new clubhouse was built, which is in operation today.
During the club's 54 year history, many events have been hosted including the PGA Tour's Tournament Player's Series (The Greater Baltimore Open), the Middle Atlantic Section PGA Professional Championship, the Maryland State Golf Association's Open Championship, Amateur Championship, the USGA U.S. Open Qualifier, the Women's Eastern Amateur Championship and numerous collegiate and charitable competitions.