Hit the Trails: New Run and Hi-LO Trail Updates
- Hillsdale News
- Sep 9
- 3 min read
Updated: Sep 10
[September 9, 2025]
Contributed by Lisa Caballero for SW Trails PDX
For eight Portlanders there was no better place to be on a fine mid-summer day than Gabriel Park, suited up, shoes laced … at six in the morning.
It was the kick-off of the SWTrails monthly run.
The run was organized by Tyler Webber and it will be a regular SWTrails event, along with our two monthly hikes and work parties. Tyler has been running the trails for a decade, since he moved to southwest Portland, and has always appreciated having safe, peaceful routes close to home. The organized run is his way of “giving back.”
Tyler has set up a Strava page (an app for tracking running, cycling and walking) for the “Southwest Trails Running Group,” and so far 16 folks are following it. On their first run, the group did a five and half mile loop, beginning in Gabriel Park, through Woods Memorial Park, Multnomah Village, and then returned on surface streets.
To get email notifications when runs are scheduled, sign up here.
And about that 6:00 AM start? It’s a chance to get a run in before work.
Tyler is also a regular attendee of the SWTrails board meetings, held over zoom. The meetings aren’t just for board members! Everyone is welcome. If you have an idea to share, or just want to be better informed about what is happening in the area, please join us, we’d love to meet you.
Coming up soon: the Hi-LO trail
The Hi-LO trail is a 6.3-mile route from Hillsdale to Lake Oswego which, with the support of Senator Rob Wagner and Representative Andrea Salinas, received an Oregon Community Paths Program grant from the State Legislature in 2021.
One feature of the trail which is a first for SWTrails will be the eleven informational signs placed along the route. These will be larger signs which will orient the walker, highlight features on the neighboring trail segment, and will have a QR code linking to more in depth information about the history, geology, flora and fauna of the route. These in-depth reports have been researched and written by by a skilled collection of scholars, journalists and enthusiasts.
SWTrails arcGIS guru Brian Brady is also putting together what is called a StoryMap, an interactive online map which links the in-depth reports to trail locations and will be a resource for those interested in learning more about southwest Portland.
The Hi-LO project is close to completion, but as anyone who has grappled with a large project will tell you, the last 5% is the hardest part. Our last 5% is to get the final approvals for sign placement, size and content—no small feat given that the signs will sit on private property, public property, a city park, a state park, and City of Portland right of way. Six governmental organizations in total. And, in addition to the eleven information boards, there will be 72 new way-finding signs along the route. SWTrails founder Don Baack is spearheading the effort, with the help of Joe “the sign guy” Fram and District Four City Councilor Eric Zimmerman.
We are happy to report that approvals are moving along. Many of the way-finding signs are already in place, and the informational signs should be up by December. Clear, regularly spaced and attractive signage is critical for the comfort and safety of walkers, and SWTrails very much appreciates the ongoing support of the individuals and groups who manage the land through which the trail passes.
The Hi-LO trail is walkable now, and should be formally open, with completed signage, in early 2026. Stay tuned for the grand opening! Keep up with what is happening at SWTrails by visiting our webpage SWTrails.org, or joining our email list to receive notices of walks, runs and work parties.
Editor's note: Access to the Hi-Lo Trail at Wells High School may be affected if Portland Public Schools closes the west parking lot during the three-year campus rebuild. See the related article, Hillsdale Farmers’ Market and HNA Team Up to Safeguard Market’s Future, for more information.
