During King William's War, Benjamin Church helped defend the British settlers on this site in September 1689 against Canadiens, and tribes of the Wabanaki Confederacy.

Goodwin's vision largely survives today, except only for the loss of a small portion of the park's north side, for the construction of Interstate 295.

[2] Deering Oaks Pond at one time filled and drained with the ocean tides; it was naturally connected to Back Cove until altered to suit roadways in the late 19th century.

Deering Oaks Park also hosts the city's monument to the Spanish–American War, a casting of The Hiker by Theo Alice Ruggles Kitson.

[6] Deering Oak's Castle-in-the-Park was built in 1894 as a warming hut for ice skaters and is located next to the pond on the State Street side of the park.

[4] In 1996 Deering Oaks Pond served as the backdrop for an ice skating scene in the film "The Preacher's Wife" starring Whitney Houston and Denzel Washington.

In 2010, Portland received a federal grant worth $1.2 million to line the bottom of Deering Oaks Pond, with a local match of $540,000.

The project was designed to promote water quality, which was harmed by algae blooms in the summer due to organic material settling on the bottom of the pond, and to prevent structural damage.