Milwaukie–Lake Oswego Heritage Trolley

If you’ve ever lived in or visited Milwaukie, you know there is one natural barrier along its western edge: the Willamette River. This beautiful resource has long drawn people to the water, but crossing it is another story. To cross it, you must head north to Sellwood or south to Oregon City. This stretch of the Willamette has long lacked any bridge or ferry connection between Milwaukie and Lake Oswego.

There is one exception, albeit a private one. The Lake Oswego Railroad Bridge, owned by Union Pacific and leased by the Portland & Western Railroad, quietly spans the river and provides the lone connection between Milwaukie and Lake Oswego. Using the bridge as a public connection beyond the infrequent freight it carries has been studied before, most recently by Metro in 2010. That study focused on modifying the bridge to add a multi-use path alongside the tracks. But what if, instead of rebuilding or expanding the bridge, we worked within the existing constraints of its current railroad use?

Tourism, Not Commuting

A seasonal, low-speed heritage trolley could connect Milwaukie and Lake Oswego using existing rail lines, operating within current railroad constraints and with little modification to existing rail infrastructure. This would not be commuter rail. It wouldn’t be frequent, fast, or designed to replace car trips. Instead, it would be a destination experience, inspired by the Willamette Shore Trolley that already runs between Lake Oswego and Portland. This summer weekend only experience could draw Milwaukie residents to Lake Oswego on Saturdays to Millenium Park for their Farmer Market. On Sundays, the primary attraction would switch shores and highlight the Milwaukie Farmers Market. Both markets are well renowned in the metro area and deserving destinations on their own, but beyond them, each city offers its own unique downtown experience to explore.  

Rendering of people loading onto a trolley in Downtown Milwaukie

Modest Infrastructure Additions

For the most part, the primary infrastructure needed to make this route viable is already in place. The rail corridor exists, and a partnership with the Willamette Shore Trolley to expand operations onto a second line would reduce the need to acquire additional trolley vehicles. Only a few targeted improvements would be required:

• First, a small, rail-level platform terminus in Milwaukie. At its most basic, this would involve minor grading and signage near the existing Orange Line MAX station. Locating the stop here would take advantage of nearby parking at the south end of downtown Milwaukie.

• Second, a crossover track connection in Lake Oswego would be needed to link the Willamette Shore Trolley line with the Union Pacific rail line. The two tracks run parallel at a similar grade, making a low-speed connection feasible. Assuming minimal interlocking and only minor grading adjustments, this crossover represents the largest capital investment in the project, with a preliminary cost estimate in the $500,000 to $1.2 million range.

Map highlighting the existing railroad connection between Milwaukie and Lake Oswego

The Ride

The 2.25 mile one-way trip (4.5 miles round-trip) would begin in Lake Oswego, heading north before quickly turning east to cross the Willamette River. From the bridge, riders would enjoy an elevated perspective with sweeping views of the river below and the resident birds of prey that call the bridge home. 

After crossing the river, the route follows the trestle along the east bank, turning north as it passes through the mature trees of the Island Station neighborhood. The ride continues over Kellogg Creek before arriving in downtown Milwaukie, just steps away from Main Street and Milwaukie Bay Park. 

Economic Activation, Not Nostalgia 

Using the existing Willamette Shore Trolley as a reference point, a summer weekend trolley drawing 10,000 riders per season could generate nearly half a million dollars in local economic activity annually, once spending at restaurants, shops, and downtown businesses is counted and ripple effects are included. Of that total, Milwaukie alone could realize roughly $175,000 in net new economic gain each year. That money would circulate through downtown, support local jobs, and strengthen the city’s overall fiscal health. It reflects people spending time and money in places worth lingering.

This idea should be viewed in the same light as a community project like the Milwaukie Bay Swim Dock, which combines a modest footprint with an outsized impact. Just as the dock can transform an underused stretch of riverfront into a destination, a seasonal heritage trolley could draw visitors beyond typical tourist circuits, encourage residents and regional visitors to linger downtown, and provide local businesses with reliable weekend foot traffic. And because the core infrastructure is already in place, the required capital investment is far smaller than most transportation projects, underscoring what becomes possible when we focus on unlocking the potential of what we already have.

Connection Reimagined

The Milwaukie–Lake Oswego heritage trolley is not a proposal to remake the region’s transportation system, but an opportunity to reimagine how an existing asset could serve the public in a new way. By working within the constraints of today’s railroad infrastructure, this concept offers a low-risk, seasonal experiment rooted in tourism, placemaking, and economic activation rather than daily commuting. It builds on the success of the Willamette Shore Trolley, aligns with Milwaukie’s growing identity, and creates a rare, car-free connection across a stretch of river that has long divided neighboring communities. In doing so, it uses what we already have to bring people not just across the river, but into downtowns, parks, and the shared story along the Willamette.