Trolley Trail

This six-mile trail is a community treasure waiting for you to explore on foot or on bike! The Trolley Trail offers a leisurely, mostly flat route that winds through peaceful neighborhoods, providing connections to schools, parks, playgrounds, riverfront access, faith-based organizations, and vibrant business districts stretching from Milwaukie to Gladstone. As part of Metro’s regional trail system, the Trolley Trail links with the Springwater Corridor to the north and provides easy access to the nearby MAX Orange Line. 

Along your journey, be sure to stop at the beautiful Stringfield Family Park and Milwaukie Bay Park, perfect spots for a rest or picnic. Keep an eye out for unique installations and sculptures from local artists that add a touch of creativity along the trail. The trail also passes through Historic Downtown Oak Grove, where you can find a bike repair station equipped with everything you need for on-the-go maintenance—like screwdrivers and Allen wrenches for unexpected flat tires. 

North Clackamas Parks and Recreation District and Metro secured a right-of-way to build the Trolley Trail in 2001, using a voter-approved bond measure designed to protect nature and help people enjoy it. The Trolley Trail was made possible thanks to a broad coalition of partners, including private citizens, community groups, businesses and governments.

A TRANSPORTATION ODYSSEY

This bike and pedestrian trail follows the historic Portland Traction Company streetcar right-of-way that ran in the area from 1893 until 1968. 

Before 1893, area residents rode in horse-drawn carriages down dirt streets or traveled into Portland on the Willamette River. That changed when a streetcar line opened between Portland and Oregon City, giving rise to bedroom communities along the route. 

By the 1920s, trolley travel reached its peak but soon began to wane as automobiles changed the landscape and the Great Depression slowed economic activity. Ridership rose again during World War II, as workers at Portland’s wartime shipyards were encouraged to save gasoline needed for the war effort by riding public transit. 

Passenger service stopped altogether in 1958, while freight service continued until the line was abandoned a decade later. A local high school teacher eventually initiated a campaign to preserve the corridor as a trail. This vision took several decades and many dedicated advocates to achieve, but it paved the way for today’s Trolley Trail.