The rink opened in 1905 and represents the longest and richest story of a roller skating rink that survived the civil strife of the 1950-60s, development overtures and the musical whims of generations to become a rink gifted for perpetuity. Today, the Oaks Skating Rink remains America's largest and oldest under the umbrella of the Oaks Park Association, a nonprofit organization that manages both the rink and park attractions.

During the Great Depression, admission prices were reduced so families could better afford skating. Additionally the park owner, Edward Bollinger, started the Junior Roller Skating Club which skated on Sunday afternoons. This led to the largest number of active roller skaters ever at Oaks Park Skating Rink.

Built in a flood plain, in 1948, water damage from the same flood that destroyed Vanport required five months to repair. During rebuilding, engineers installed iron barrels under the rink floor so it could float above flooding waters in the future. The rink flooded again in the Christmas flood of 1964 but it suffered some damage because workers could not immediately access the rink due to 8 feet (2.4 m) of flooding waters in the park. A day later and after four hours of effort, they severed the floor supports to allow it to float.

Dale and Jeanne Pritchard were longtime instructors at the rink.

The rink has served as a location for several films and television episodes. It appears in Grimm and Portlandia, a 2011 episode of Leverage, and 1989's Breaking In with Burt Reynolds.

In 2017, Damian Lillard and Adidas released a version of his "Dame 4" shoe, called "Glow in the Park", which was inspired by the rink.

Today, the Oaks Rink carries the tagline "Skaters Paradise" to accompany its 100 x 200 square foot (20,000 sq ft skating surface) Michigan maple floor and the last live Wurlitzer pipe organ to operate in a U.S. roller rink

According to wikipedia

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