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Trolley Trail tour: You can now ride Portland to Oregon City nearly carfree (photos)


There are many signs along the route to help you along.
(Photos and words by Adam Herstein)

— This post was submitted through our subscriber post system by Adam Herstein.

It’s easier than you think to venture down to Oregon City. (Map details here)

We finally got a bit of dry weather, so I decided to do a ride that I’ve been contemplating for a while now – riding the Trolley Trail from my home in SE Portland to Oregon City. The bicycle infrastructure along the Orange Line, the new SE 17th Avenue cycleway in Milwaukie, the Trolley Trail through Milwaukie and Gladstone, and various paths along the Clackamas River, combine to form a nearly 100 percent carfree route for the 20-mile journey.

The carfree portion starts at the Portland-Milwaukie border near Sellwood. Getting to this area used to require an uncomfortable ride along SE 17th in Sellwood. But now, once you leave Portland, there is a completely separated cycleway that takes you to Milwaukie’s Waterfront Park. Upon reaching Milwaukie, one can easily connect with the Trolley Trail that takes you all the way to a walking-and-cycling-only bridge over the Clackamas River at Gladstone. The newly-completed Trolley Trail primarily consists of a car-free multi-use path with a few low-traffic, sharrow-marked streets.

Overall, the path feels very comfortable and safe. The only sketchy part was a two-stage crossing of McLoughlin Boulevard. A bridge over this busy thoroughfare would have been useful here.

The Trolley Trail ends at an old truss bridge that has been converted to a bike and walk crossing over the Clackamas River. From there, various paths along the river will take you to Clackamette Park and on to Oregon City. There was a ton of construction going on along this path but the detours were well-signed and easy to ride in. There was even a permanent barrier-separated cycleway underneath I-205 and alongside McLoughlin! This path took me directly to downtown Oregon City, where I enjoyed a cold beer at Oregon City Brewing.

This was a great ride on comfortable paths and roads that nearly anyone can tackle. The bike routes were well signed and there was plenty of beautiful scenery to look at. What I liked about this route was that you’re never far from civilization or a TriMet bus route in case something happens (luckily everything went smoothly for me). It took me about two hours to ride the 15 miles from SE Portland, as the paths encourage a slow, leisurely pace. I highly recommend this route! (If you’d like detailed directions, I mapped out the route on Strava.)

Follow along on my journey via the images below…

Typical cross-section of the Trolley Trail.

Tricky crossing McLoughlin Boulevard here. Had to ride up onto the sidewalk.

Old Clackamas River truss bridge converted to bike and walk access only.

The Trolley Trail near the Park Ave MAX Station. The trail through Milwaukie ran alongside peoples’ backyards.

Trolley Trail near Gladstone.

Some portions of the Trolley Trail are on low-traffic streets with sharrows.

Other parts of the Trolley Trail were separated cycleways along busier streets.

Path near Oregon City along the Clackamas River.


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Excellent cycling facility under I-205 and separated from a dangerous ODOT road.

Clackamette Park in Oregon City.


The confluence of the Clackamas and Willamette Rivers.

Some sort of apartment complex is going in here.

Lovely day for a bike ride!

Beautiful river views!

Oregon City is cool.



Thanks for the beer Oregon City! And for the great ride.


— Adam Herstein is a BikePortland subscriber.

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