This simple self-led hike is a companion to Hike # 13 through historic Ainsworth.  Both hikes #13, and #16 begin and end at Ainsworth Elementary school.  They could be combined into a longer hike that totals just under 5 miles, or done independently.

Name: Ainsworth Loop West
Neighborhood: Southwest Hills
Distance: 2.55 Miles
Rating: Easy
Elevation Change: 207 ft
Start/End Location: Ainsworth Elementary School
Map Links:  Interactive Map

This hike is a short stroll through the western part of the Portland Heights area where you’ll cross an enchanting bridge, pass colossal early-century houses and climb Portland’s steepest switchback road.

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:
Before heading out, take a moment to explore the gardens on the south side of Ainsworth Elementary School. There is a nice little wayside with a bench dedicated to Phyliss Towne, a co-founder of SWTrails and our long-time hike leader/coordinator.

The route begins by following a unique pedestrian bridge across a forested canyon to Montgomery Dr where you turn left. Climb along this narrow street with intermittent sidewalks to enjoy the historic buildings of old Portland. On the left, you’ll pass the historic 1918 Frank J. Cobbs house, one of the larger estates in all of Portland, at 2424 SW Montgomery. This colossal dwelling is almost 15,000 sf of living space with 6 baths and 3 half baths. It last sold for $4.4 million in 2002. Per county records, the current property tax bill comes to an astounding $83,000 per year!

After you pick up your jaw from realizing the extraordinary sum spent on taxes, continue along SW Montgomery Dr to SW Upper Dr. Descend along Upper Drive until it turns into English Ct. Turn Right at English Ln, until you reach Patton Rd. Turn Left at Patton Rd and follow it to the complicated 6-way intersection of Patton, Vista, Broadway, Talbot, Greenway and Audrey.  Take the second strong left to Vista Ave, and follow it among more colossal houses to SW Hillcrest Dr on your right. This street resembles San Francisco’s Lombard street with its steep curvy one-way-down travel lane. As you begin your climb on this steep grade, be careful to watch for cars and stay to the right so they can see you. The sight distance is short here as you can see on the map. In a few hundred feet you will come to SW Ravensview Dr where you’ll turn left. When you arrive at Terrace Dr, turn left. This is the route of SW Trail 6 from downtown Portland to Lake Oswego.

Stay on Terrace until it turns right and assumes the name of SW Elizabeth Street. Follow SW Elizabeth to SW 18th and turn left for one block to SW Spring St. Stay on Spring St for 2 blocks to the Vista Springs Café on the corner of Spring and Vista. There is also a fire station across the street in case you need to have your blood pressure checked! On the west side of Vista Ave is Ainsworth Elementary School where you began.

*To follow this route, use the Explorer for ArcGIS App to follow along. Simply Download the Explorer for ArcGIS app and touch here on any mobile device. The route is highlighted on an interactive map.

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

Happy Trails,







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