In the first half of the twentieth century, Freeport had three golf courses. By the second half of the century, all the courses were replaced by residential development.
The Freeport Golf Club, established on June 22, 1900, was located south of Merrick Road and west of Bayview Avenue. Cedar trees bound the 2,494-yard, nine-hole course with five bunkers. The club was organized during a meeting at the Crystal Lake Hotel in which William A. Hope of Brooklyn presided and Ernest S. Wallace recorded, and a constitution and bylaws were adopted. Originally, there were 72 members and membership was limited to 150 members. Johnnie Dunn, the former caretaker of the Montclair New Jersey Club, was hired to redo the course and John Turnbull was hired as the golf club's caretaker and professional instructor. W. T. Miller, Charles L. Wallace and Daniel B. Raynor were among the club's governors. In 1900, John C. Kelley was elected president of the Freeport Golf Club and Herbert F. Gunnison served as vice president.
The course was first played on July 4, 1900. In 1901, ground was broken for a clubhouse designed by architect Woodruff Leeming and constructed by the firm of Randall and Miller. The clubhouse featured a veranda, an assembly hall with cathedral-style windows, and a fireplace. Locker rooms were available for both men and women. Tournaments were held throughout the season. Guests of members were charged 50 cents per day or $5 per month to play the links.
In 1902, the Freeport Golf Club incorporated. Its directors included: George F. Taylor, Frank Arguimbau, Frederic E. Story, Daniel Arguimbau, Frederic R. Vernon, Charles L. Wallace, William G. Miller, Hamilton G. King, John W. Bailey, Horace Secor, Jr., and John C. Kelley.
The Milburn Country Club (also known as the Manhattan Country Club, the Milburn Golf Club, and the Willowbrook Golf Club) was a golf course developed in the northwest section of Freeport next to Milburn Creek, which extended from Stearns Park to Grand Avenue. Hugo Stearns originally established a nine-hole golf course in this section. In 1917, organizers of the Manhattan Country Club purchased the land from Hugo Stearns for $250,000 and expanded the course to 18 holes. Officers of the club included Hiram Smith, August V. Lambert, C. D. Baker, Daniel W. Blumenthal, William H. Fleisch, and Leopold Prince. Smith, a Freeporter, was also the supervisor of the Town of Hempstead. Prominent golf architect Devereux Emmet designed the course. The club officially opened on Decoration Day (now known as Memorial Day) in 1917.
In 1919, membership dues were $100 and an initiation fee was waved for early applicants. For many years the club catered to primarily Jewish patrons. In 1920, the links were reorganized as the Milburn Golf Course by William Fox of the 20th Century-Fox movie studio, Marcus Loew of the theater family, and George Z. Macadie, former U.S. Attorney General.
In 1941, new ownership opened the golf course to the public. A 14-lane bowling alley was added to the club in 1942. That same year, Joseph F. Mittelmari and associates purchased for residential development nearly 100 acres owned by the golf course. On February 1, 1943, the club was destroyed by a fire. During the blaze, David Armstrong, a locker man at Milburn, saved the life of a waiter named Victor Larsen, who was asleep in his room on the second floor. Soon after the fire, the club was reorganized as the Willowbrook Golf Club. In 1949, the Long Island open tournament was held at the Willowbrook Golf Club with professional golfer and Long Island native Al Brosch taking first place. In 1952, the Baldwin School District assumed ownership of the remaining 35-acre property.
The Woodcleft Golf Links was a golf course located in southeast Freeport in the 1920s. Its boundaries included South Grove Street (now Guy Lombardo Avenue) to the west, Hudson Avenue to the east, and King Street (possibly Jefferson Street today) to the north. The course was located just south of Playland Park. After streets were constructed, in 1935, plots of land were sectioned off and sold for residential development.