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Walking Lake Oswego: Millennium Park, Oswego Lake, Lakewood Bay, Jantzen Island

This 4+ mile, rolling hills (moderate to steep) stroll through Lake Oswego’s north lakeside neighborhoods is serene and mostly shaded (perfect summer escape).

Thinking of walking beautiful Lake Oswego? This 4+ mile walk through the Evergreen and North Shore Country Club neighborhoods, along the north shore of Oswego Lake, delivers stunning views of the lake and some of the most spectacular lakeview homes in the region.

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Lake Oswego is known for its beautiful, well-maintained parks and numerous walking trails, making it ideal for lovers of the great outdoors. The pathways around Oswego Lake offer scenic views and a serene walking experience. Additionally, the streets are generally walker-friendly with good sidewalks and safe, pedestrian-focused areas.

The area’s natural beauty, combined with its friendly, safe and engaging community, makes it an excellent location for both leisurely strolls and power walking.

This route begins in Lake Oswego’s beautiful Millennium Plaza Park with sweeping views of Lakewood Bay. (That tiny red umbrella in the distance beckons from Stickmen’s Lakeside Smokehouse & Brewery, the only eatery on the lake with lakeside dining.

Take your time appreciating architectural details of luxury homes, along with lake views and gorgeous gardens. 

Walking Lake Oswego: Millennium Park, Oswego Lake, Lakewood Bay, Jantzen Island

This walk heads east down a long, wide staircase (or alternate ramp) and across an adjacent railroad track, before heading east along Headlee Walkway.


Interactive Route Map

From your computer, grab our interactive route map of Walking Lake Oswego: Millennium Park, Oswego Lake, Lakewood Bay, Jantzen Island. And then save and open from your iPhone to follow along as you walk. No more missed turns or getting lost!

Walk Directions

Join PDX Women Who Walk for a guided tour of this iconic Portland walk.

Start & End

Route Out

NOTE: Public restrooms are available at Millennium Plaza Park (and nowhere else along the route.

  1. STEPS DOWN | East, then Southeast (From Millennium Plaza Park, head down the steps leading to Lakewood Bay.)
  2. TRAIL | Right/West
  4. 3rd STREET | Left/North
  5. LAKEVIEW COURT | Left/West
  6. LAKE BAY CT | Left/Southwest
  7.  RAILROAD CROSSING | Left/Southeast
  8. CABANA LANE | Continue West
  9. NORTHSHORE RD | Continue West
  10. NORTHSHORE ROAD | Left\South then West
  11. DIAMOND HEAD ROAD | Left\Southwest (This is the steepest hill on this lakeside journey. Take it slow and enjoy the views. It’s worth the climb. You can do it! 🙂

Route Back

  1. DIAMOND HEAD RD | Turn around and walk down the steep hill.
  2. NORTHSHORE RD | Right/ East
  4. NORTHSHORE RD | Right/East
  5. CABANA LANE | Continue East (Ignore NO OUTLET sign)
  6. RAILROAD CROSSING | Left/Northwest across train track and onto path
  7. LAKE BAY CT | Right/East
  8. 3rd ST | Left/North
  9. EVERGREEN ST | Right/East


About 5 miles for complete loop.


About 2 hours.


In the beginning the route is fairly flat but then becomes progressively steep as it approaches Jantzen Island and then Diamond Head Road (which is a challenging climb, so take it slow).


Mostly flat, but somewhat difficult at Diamond Head Road, with plenty of eye candy along the route to keep you engaged.


Sturdy, well-fitting running/walking shoes are a must on Lake Oswego’s various neighborhood roadways and gravel or bark trails.


Bring it! (Your iPhone camera is great for walking photo shoots. (Here’s the one that I use that folks are always asking about: Taporse for iPhone 13 Pro Max Crossbody Wallet Case with Credit Card Holder, Detachable Crossbody Lanyard Strap )


There are two bets for coffee at the start/end of this route and for easy reference they’re indicated on the route map. In Millennium Plaza Park the options are St. Honore Boulangerie and Peet’s Coffee. Both are excellent. Our fave however is local Morse Coffee Company, across A Avenue on 1st Street. Tell owner Sam Morse we sent you. 🙂

Click Here to See Homes for Sale In Lake Oswego

Susan S. Bradley

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