The Tenth hike in our Self-Led Hike series may be the best one yet.  Why don’t you try it out and see if you agree.  Read on for more details.

Name: Hillsdale to Healy Heights
Neighborhood: Hillsdale
Distance: 4.88 Miles
Rating: Medium
Elevation Change: 512 ft
Start/End Location: Hillsdale Food Carts (Wells HS)
Map Links: Interactive Map

This route features beautiful views of the Cascades: Mt St Helens, Mt Hood, Mt Adams and (on a clear day) the top of Mt Rainier over the shoulder of Mt St Helens.   And to the west, along the earlier part of the hike, you’ll be able to appreciate the sweep of the coast range and the valleys between the Tualatin and coastal mountains. The route takes you along segments of Trails 1 and 6 through the northern part of Hillsdale, SW Hills Residential League (SWHRL) and the Healy Heights neighborhoods.

Interactive Map Directions:

  • Touch the “Interactive Map” link at the top of this page to launch a web-based version of the route map from your mobile browser (i.e. chrome, or safari).
  • Touch the locate me button in the top-left corner of your display to activate a ‘blue dot’ showing your current location
  • Your blue dot will now follow the highlighted route from your mobile device!
  • Note, you may have to grant permission to allow the application to access location services.


Step-by-step Directions:
To begin, start at the Hillsdale Food Carts and head north across Capitol Hwy, up Sunset Blvd, past Hillsdale Library, and up to SW 18th Dr. Take a right, go up and follow the curve to the left, then head straight and down SW 19th Dr. At the intersection of SW 19th and SW Sunset, take a hard right up SW 25th Ave—it’s a cul-de-sac, but at the very end, on the left-hand side, you’ll see a short path (next to a wooden fence) that ends on SW Hamilton Ct. That leads to SW 27th (take a right) then left on SW Hamilton St to a soft curve up to the right, SW Twombly. After about a block, you’ll see a home that looks like it has two driveways; proceed fearlessly up the left-hand side, as you’ll see a further path up ahead. These are the fabled Twombly Steps that are maintained by SWTrails volunteers! You will cross two streets on your way up; the third is SW Melville Ave—take a left. Melville winds its way up to a long set of steps—part of SWTrails #1—which you’ll clamber up to reach SW Fairmont Blvd. You’ll have almost reached the peak of the trip!

Take a right on Fairmont, walk along the curves, enjoying a stellar view of the Coastal Range and the valleys to Portland’s west; after the downturn that is SW 18th Dr., start looking out on your left for a set of narrow wooden steps graced by a metal handrail; go up the steps and continue, along SW Council Crest Dr., past the KGON Tower (now you’ve reached the peak) and walk until you reach SW McDonnell Terrace; head right. McDonnell takes a sharp curve to the left, then continues on down to Fairmont; you can either follow it and turn right, or take the SWTrails #6 cut-through, which drops you onto Fairmont just a bit sooner. You’ll be following Fairmont’s ins and outs heading south—savoring that eastern view between the trees—until you reach SW Mitchell Dr., to take a left and follow, essentially, SWTrails #6 all the way to Hillsdale: Mitchell turns left into SW Hessler Dr; Hessler curves down to end at SW Northwood Ave—take a right—to SW Westwood Dr—take a left—and becomes SW Menefee Dr. At the intersection with SW Westwood, take a left onto that street, and follow it all the way to head right on SW Cheltenham Ct, which you can follow all the way back to Capitol Hwy or—for a safer route—take a left on SW Dewitt, passing the fire station, Hillsdale Park and the library—take a left on SW Sunset and then down to Capitol and back across to Wells High School and the parking lot where you began.

Don’t forget to use the hashtag #swtrails to share your very best pictures.

Happy Trails,





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