Three Oaks' hometown pride is evident during its Flag Day Celebration in June.

[7][8][9] Three Oaks celebrated the centennial of receiving the Dewey Cannon at the village's Flag Day Festival (June 9–11, 2000).

A historical marker at Dewey Cannon Park in Three Oaks relates: "This cannon, captured in the Spanish–American War by Admiral Dewey, was presented to Three Oaks when its citizens raised fourteen hundred dollars for a memorial to the men of the battleship Maine.

"[10] The Dewey Cannon, which remains on display in the park of the same name, bears the engraved monogram of Queen Isabella II of Spain.

[6] Three Oaks is also home to the Warren Featherbone Factory, which was built over a century ago by Edward Kirk Warren to strip turkey feathers of their quills to use in women's garments of the era, such as corsets, which used "stiffeners".

This replacement for the "whalebone" material was welcomed by the garment industry of the late 19th century.

A financial crisis occurred in 2008, after the village proceeded with a $350,000 five block street project.

This and other expenses over the previous four years left Three Oaks a deficit of about $600,000 (about a one-year budget) by April 2008.

[11] The Village President, the Clerk, and a councilman resigned while two councilmen did not seek re-election.

[11] The state of Michigan appointed Emergency Financial Manager Pam Amato effective December 17, 2008, to take over village operations and guide the newly elected Council through development of a five-year deficit elimination plan.

The village was given a recommendation to disband its Downtown Development Authority, after an audit showed receipt of excess funds that should have gone to the school district.

[14] According to the United States Census Bureau, the village has a total area of 0.99 square miles (2.56 km2), all land.

Three Oaks was the fictional setting of the soap opera, Young Doctor Malone, on radio and television from 1939 to 1960.