Hillsdale's New Trail to Lake Oswego Opens This Saturday. Its Front Door Is About to Change.

This Saturday, September 19, at 8 a.m., a few dozen people will gather in the cafeteria at Ida B. Wells High School to celebrate something that has been two decades in the making: a walking path that finally, completely, connects Hillsdale to Lake Oswego. The HI-LO Trail runs 6.3 miles from the Hillsdale Food Carts on Capitol Highway through Marshall Park, under Boones Ferry Road, through Tryon Creek State Natural Area, and into the town of Lake Oswego. It is a genuinely good piece of civic infrastructure, built almost entirely by volunteers, and it deserves the celebration.

What most of the coverage around the opening has missed is what's happening at the other end of that same parking lot. The trail's northern anchor sits directly beside a high school that just cleared its final approval for a multi-year rebuild. Construction starts in December. The two projects were never connected to each other in planning, but they are about to occupy the same three acres of pavement at almost the same time. If you live near the Hillsdale trailhead and plan to use this trail regularly, the version you'll walk this fall is not the version you'll be walking by next spring.

Twenty Years, Six Agencies, One Path

The HI-LO Trail has been part of Metro's Regional Transit Strategy since the early 2000s, and SWTrails PDX, the volunteer group that built most of it, has been chipping away at the gaps ever since. The project cleared its first real hurdle in 2004, when Portland City Council overrode objections and placed the trail on Metro's Regional Trails System Plan map. That decision didn't build a single foot of trail. It just meant the idea had official standing, which turned out to matter for everything that came after.

The hardest technical problem was Boones Ferry Road, a busy arterial that used to force walkers through a culvert alongside Tryon Creek, the same culvert that was blocking fish migration. Portland's Bureau of Environmental Services, the Bureau of Transportation, and Portland Parks and Recreation eventually agreed on a different fix: build a pedestrian bridge over the creek instead of routing people through a pipe next to it. A similar problem existed at Taylors Ferry Road and SW 17th, a blind curve with no crosswalk at the edge of Marshall Park. The Bureau of Transportation agreed to build a proper crossing there too.

State money finally arrived in 2021, when an Oregon Community Paths Program grant, secured with support from Senator Rob Wagner and Representative Andrea Salinas, funded the last stretches: a half mile of trail through Oregon State Parks land, repairs to the SW 19th Avenue segment, the Taylors Ferry crossing, and signage for the entire six-mile route. That signage turned out to be its own small bureaucratic puzzle. The trail crosses private property, city park land, state park land, and Portland right of way, which meant SWTrails needed sign approvals from six separate government entities before a single wayfinding post could go in the ground. Eleven larger interpretive signs and 72 wayfinding markers are the visible result of that coordination work, most of it handled by longtime SWTrails volunteers including founder Don Baack and sign coordinator Joe Fram.

None of this is the kind of thing that shows up in a listing description or a neighborhood ranking. It's the kind of thing you only notice if you've been paying attention to the same six-mile stretch of Southwest Portland for twenty years, which is exactly what a small group of your neighbors has been doing.

What You'll Actually Find on the Trail This Fall

The finished route is more than a paved connector between two commercial districts. Along the way you'll pass restored wetlands, a waterfall, and stretches of forest inside Tryon Creek State Natural Area, along with a playground and a visitor's center. The trail is pedestrian-only, dogs are welcome on leash, and it isn't built or signed for bikes.

The eleven interpretive stations are the trail's most distinctive feature. Each one includes a QR code linking to a longer piece written by a local historian, geologist, or naturalist, covering everything from the Tryon family's original 1850 land claim to the Oregon Iron Company smelter that once operated where George Rogers Park sits today. SWTrails volunteer Brian Brady has also built an interactive online StoryMap that ties all eleven stops together, so you can read the history of a specific creek crossing or forest segment before or after you walk it, not just while standing in front of a sign.

If you're picking a starting point, the route runs through eleven named trailheads: the Hillsdale Food Carts, the Raz-Baack Crossing near Stephens Creek, SW 19th and Capitol Hill Road, Barbur Boulevard, Taylors Ferry Road, Marshall Park, Arnold Avenue, North Creek, Iron Mountain in Lake Oswego, State Street and B Avenue, and the Lake Oswego Transit Center. You don't need to walk all 6.3 miles at once. Most SWTrails regulars treat it as a set of connectable loops, the same way the group's monthly hikes and its newer running group, organized by longtime Southwest Portland resident Tyler Weber, already do.

Why the Trailhead Won't Stay the Same

Here's the part worth sitting with. Ida B. Wells High School, at 1151 SW Vermont Street, sits at the Hillsdale end of this trail, and its parking lot and adjacent fields are effectively the trail's front door on that side. On September 4, 2026, the Portland Design Commission gave full approval to a modernization plan for the school, designed by Bora Architecture with Hoffman Construction as contractor. The project will build a new 295,000-square-foot, four-story building on the portion of the site currently occupied by Clopton Field and an auxiliary grass field, funded through the district's 2025 bond measure. Construction is scheduled to begin in December 2026, with the new building opening in fall 2029 and new athletic fields complete by fall 2030.

The detail most relevant to trail users involves Rieke Road, the paved path separating Wells from Mary Rieke Elementary School next door. It currently allows car access during school hours and doubles as the seasonal site for the Hillsdale Farmers' Market. Under the approved design, that road will get bollards and gates limiting car access while still allowing cyclists through outside school hours. Combine that with relocated athletic fields, a repositioned main building on the south edge of the property, and an expected increase in drop-off traffic along SW Vermont, and the general layout of the Hillsdale trailhead area is going to look different by the time the new school opens.

None of this changes the trail itself. The HI-LO route doesn't run through the construction footprint, and the celebration this Saturday is a genuine milestone worth showing up for. But if you're the kind of person who parks near the school to start a walk toward Lake Oswego, or who cuts through on Rieke Road on your way somewhere else entirely, the next few months are the window to get used to the current setup before it starts shifting. Construction crews mobilize in December. Whatever routine you build around this trailhead between now and then is worth paying attention to, because it's the version that won't last.

A Neighborhood That Finishes What It Starts

There's a pattern in how this trail got built that says something real about Southwest Portland. Nobody handed SWTrails a budget and a deadline. A volunteer-run nonprofit spent twenty years negotiating with six different government agencies, one creek crossing and one crosswalk at a time, because enough people cared about a six-mile idea to keep showing up to Zoom board meetings and Thursday morning work parties. That's not a marketing story. It's just how things get done here, and it's worth knowing if you're going to be walking these paths for years to come.

If you're new to the area, or you've lived here for decades and just haven't had a reason to think about Marshall Park's north end, this is a good season to go find out what your neighbors built. Show up Saturday if you can. If not, the trail isn't going anywhere, even if the parking lot at one end eventually will.

If you're weighing a move to Hillsdale or anywhere else on Portland's Westside and want a clearer sense of how a neighborhood actually functions day to day, not just what the listing photos show, Shannon Janssen can walk you through it. Let's Connect.