Oakland Lake was formed about 15,000 years ago as a kettle hole (a depression made in the ground as a result of glacial movement). The lake is fed by underground springs and a ravine with overflow running east to Alley Creek. Once called Mill Pond, and then Douglas Pond, the lake was originally part of the John Hicks estate, an early settler and recipient of the Dutch land grants in 1645.

​

In 1874 the Village of Flushing purchased the lake and adjoining 12 acres as a municipal water source. The name was then changed to Oakland Lake in honor of "The Oaks," the 340-acre estate bordering the lake owned at that time by John Taylor. As the new owners, Flushing built a pumping station and laid pipe line along Northern Boulevard to deliver water to the Village of Flushing. A few years later the water main was tapped to supply a few sections of Bayside. After the City consolidated in 1898 the lake was no longer needed as a water source since the City began receiving water via upstate reservoirs and aqueducts.

​

By 1934 title to the lake was transferred to the City of New York Department of Parks. Unfortunately, it was during this time that the Works Progress Administration (WPA) lined the brook and small pond leading to the lake with cement. In 1941, the Health and Sanitation Departments again engaged WPA workers with laying pipes, filling in and grading low areas as well as digging drainage ditches in an attempt to control the mosquito population.

​

The wetlands ecosystem was further destroyed as a result of the construction of an elementary school, Cardozo High School, and Queensborough Community College during the 1960s.

​

According to the New York City Parks Department: "In 1969, 2,000 people participated in a "Walk in the Alley" led by Dr. John O. Riedl (1905-1992), a dean at Queensborough Community College who chaired the Alley Restoration Committee. The group, calling for the improvement of Oakland Lake, met with Parks Commissioner August Heckscher (1913-1997) and secured a commitment from Parks to speed up plans to rehabilitate the lake. The John Reidl Wildflower Meadow in Alley Pond Park commemorates Reidl for his efforts on behalf of the preservation of the park. Community pressure to protect the park remained steady through the 1970s and 80s. Gertrude Waldeyer (1908-1987), for who the lake's promenade is named, organized a grass-roots effort to preserve the lake for future generations. A local educator and member of Community Board 11 and the Bayside Historical Society, Waldeyer founded the Oakland Lake and Ravine Conservation Committee. She succeeded due to her hard work; in 1987, Parks spent nearly $1 million to restore Oakland Lake to its natural state."

​

In 1988 the New York State Department of Environmental Conservation designated Oakland Lake and the surrounding area as freshwater wetlands.