Lake Oswego Loop
Length: 26 Miles
Elevation Gain: 2042 ft
Highest Point: 493 ft
Recommended Gearing: 39X23 or equivalent
Starting out on the Eastbank Esplande path under the Hawthorne Bridge, head into downtown and work your way up to OHSU and Terwilliger Blvd. I’ve found traveling through downtown in Portland to be rather safe and easy. The lights are often synchronized, so a steady pace will allow you to shoot through without much trouble. And most roads are one-ways, so all traffic is heading in your direction.
Terwilliger Blvd will lead you to the Tryon Creek State Park. Here, the best bike path in the city awaits, as you parallel Terwilliger, but in the trees. This path offers awesome shelter on hot summer days as well as cool and wet fall rides. The visitor center has water fountains and bathrooms also.
The Tryon Creek path drops into Lake Oswego. You’ll quickly approach the lake itself on your right and see a lot of interesting artwork. Just past the lake, turn up McVey Ave and take that to Southshore Blvd. There is a small path to the side of Southshore to follow if you like and a view point at the top with a water fountain.
Follow Southshore around the lake until you’re on Lakeview Blvd. Detour off of this onto Summit Dr. This is a nice little climb that you certainly will notice, but the views of the lake and of the incredible homes will offer some distraction.
Iron Mountain leads you back towards the Tryon Creek Path. Climb back up the path and follow your original route back to downtown along Terwilliger. Two more water fountains can be found on Terwilliger if needed.