There are certain activities that just feel built for kids. Riding a trolley is one of them.
Maybe it is the bell. Maybe it is the old-fashioned charm. Maybe it is the fact that, for once, your child is excited to sit still for 90 minutes without needing a screen, snacks, a legal contract, and three emergency backup plans.
Whatever the magic is, the Willamette Shore Trolley has it. And good news for families: it returns for the 2026 season on Memorial Day weekend, with rides beginning Saturday, May 23. The trolley runs Saturdays and Sundays through the summer, plus Memorial Day and Labor Day, making it an easy weekend adventure for families looking for something a little different.
The Willamette Shore Trolley travels between Lake Oswego and Portland along the west side of the Willamette River. The full roundtrip is about 10.5 miles and takes around 90 minutes, which is a great length for kids. Long enough to feel like an adventure. Not so long that everyone starts emotionally unraveling by the halfway point.
The Lake Oswego depot is located at 311 N. State Street, right near downtown Lake Oswego. From there, the trolley heads north toward Portland, passing wooded areas, river views, neighborhoods, trestles, and one of the best kid-friendly highlights of the trip: the Elk Rock Tunnel. The tunnel opened in 1921 and gives the ride that perfect “whoa, we’re really doing this” moment for younger passengers.
The Portland terminal has temporarily moved one block south from Moody and Bancroft. For now, riders should use the stop in front of the Tesla Building at 4333 S. Macadam Avenue. The stop is also about two blocks south of the Lowell Street stop on the Portland Streetcar.
There is a lot of history packed into the route. The rail line dates back to the 1880s, when it began as a narrow-gauge steam railroad linking Portland to Oswego, as Lake Oswego was then known, and south into the Willamette Valley. In 1914, the line was electrified, and Red Electric interurban trains carried riders to Portland, Beaverton, Hillsboro, Newberg, McMinnville, and Corvallis. Passenger service ended in 1929, freight service continued until 1983, and the Willamette Shore Trolley began operating in 1987.
Today’s trolley is a vintage-style ride operated by the Oregon Electric Railway Historical Society. It feels like a step back in time, but without requiring parents to explain why nobody had Wi-Fi in 1921.
For families, the appeal is simple. This is not a giant theme park day. It is not a 12-hour road trip. It is a slow, scenic ride through a beautiful stretch of the Portland area that many kids have probably seen from a car window, but never from the rails. You get river views, local history, a little bit of transportation nostalgia, and enough novelty to keep kids interested.
The schedule is also family-friendly. From May 23 through September 7, trolleys depart Lake Oswego for Portland at 10 a.m., noon, 2 p.m., and 4 p.m. Those trips arrive in Portland at 10:40 a.m., 12:40 p.m., 2:40 p.m., and 4:40 p.m. Return trips from Portland to Lake Oswego leave at 11 a.m., 1 p.m., 3 p.m., and 5 p.m., arriving in Lake Oswego at 11:40 a.m., 1:40 p.m., 3:40 p.m., and 5:40 p.m.
From September 12 through September 27, the schedule shortens. Lake Oswego departures are at noon and 2 p.m., arriving in Portland at 12:40 p.m. and 2:40 p.m. Portland departures are at 1 p.m. and 3 p.m., arriving in Lake Oswego at 1:40 p.m. and 3:40 p.m.
Tickets are sold one-way online, so families should make sure to buy tickets for the return trip too if they plan to ride both directions. Limited walk-up tickets may be available if online tickets sell out, but as any parent knows, “maybe” is not exactly the word you want to build a family outing around.
Roundtrip fares for 2026 are $22 for adults, $20 for seniors and military with ID, $12 for children ages 2 to 12, and free for kids 2 and under. One-way tickets are $11 for adults, $10 for seniors and military, and $6 for children ages 2 to 12.
One important note for families: seats are not assigned, and riders are asked to arrive 15 minutes before departure. The trolley is also not wheelchair accessible, as there are three steps to enter and reach the passenger seating area.
To make a full outing of it, start in Lake Oswego and ride north, or begin in Portland and roll south into downtown Lake Oswego for lunch, a walk, or a treat. Lake Oswego’s downtown area is easy to wander, and the trolley ride gives the day a built-in centerpiece. It is the rare family activity where the transportation is the attraction.
And that might be the best part.
Kids spend so much time being rushed from place to place that a trolley ride feels almost radical. It is slow. It is scenic. It invites everyone to look out the window. It turns a simple stretch between Lake Oswego and Portland into something memorable.
The Willamette Shore Trolley is not just a ride. It is a little moving museum, a little local adventure, and a very Oregon way to spend a summer weekend.
All aboard. Just maybe bring snacks. Because history is fun, but children are still children.
Tiffany Wilson is a 42-year-old stay-at-home mom from Tigard, Oregon, raising three kids—Sophie, Noah, and Riley. She’s a warm, hands-on parent who mixes daily routines with creative fun, whether it’s a backyard scavenger hunt or building a blanket fort in the living room.