What is now Captain Tilly Park was formerly located on land owned by the Tilly family.
The park was originally called Highland Park.
The Highland Park Society was founded c. 1891 to "provide a park and playground" for Jamaica.
Initially the park land was worth $3,000, but by 1908 the park was thought to be worth ten times that amount.
That year, Highland Park was transferred to city operation, with the Tilly family giving the land to the city for $1 on the condition that it would permanently remain as a park.
The name was changed in 1912 to Upland Park because of possible confusion with the larger Highland Park in Brooklyn.
The next year, the city approved the acquisition of 3.216 acres (1.301 ha) of land to expand Upland Park.
Simultaneously, another 1 acre (0.40 ha) was given to the city by another landowner.

The city took property title to the park in 1925.
The next year, Goose Pond was drained due to construction of Jamaica High School across the street.
The city planned to expand the park in conjunction with the school's construction.
However, community members objected to the excessive amounts that would be disbursed to affected landowners, since residents near the park would have to pay extra taxes.
In 1938, after years of extended lawsuits, a judge reduced the disbursements for the affected parcels by more than 50%.

The city authorized the park's name to be changed to "Captain Tilly Park" in early 1935, and the renamed park was dedicated that August.
The park's namesake, Captain George H. Tilly, had been killed in 1898 during the Spanish–American War.
In conjunction with this renaming, the park was renovated with new benches and lamps, improved landscaping, and deepening of Goose Pond.
At the time, the park comprised about 7.75 acres (3.14 ha).
A Spanish-American War heroes' monument was erected in the park in 1941.
What is now Captain Tilly Park was formerly located on land owned by the Tilly family. The park was originally called Highland Park. The Highland Park Society was founded c. 1891 to "provide a park and playground" for Jamaica. Initially the park land was worth $3,000, but by 1908 the park was thought to be worth ten times that amount. That year, Highland Park was transferred to city operation, with the Tilly family giving the land to the city for $1 on the condition that it would permanently remain as a park. The name was changed in 1912 to Upland Park because of possible confusion with the larger Highland Park in Brooklyn. The next year, the city approved the acquisition of 3.216 acres (1.301 ha) of land to expand Upland Park. Simultaneously, another 1 acre (0.40 ha) was given to the city by another landowner.
The city took property title to the park in 1925. The next year, Goose Pond was drained due to construction of Jamaica High School across the street. The city planned to expand the park in conjunction with the school's construction. However, community members objected to the excessive amounts that would be disbursed to affected landowners, since residents near the park would have to pay extra taxes. In 1938, after years of extended lawsuits, a judge reduced the disbursements for the affected parcels by more than 50%.
The city authorized the park's name to be changed to "Captain Tilly Park" in early 1935, and the renamed park was dedicated that August. The park's namesake, Captain George H. Tilly, had been killed in 1898 during the Spanish–American War. In conjunction with this renaming, the park was renovated with new benches and lamps, improved landscaping, and deepening of Goose Pond. At the time, the park comprised about 7.75 acres (3.14 ha). A Spanish-American War heroes' monument was erected in the park in 1941.
Captain Tilly Park