The Trolley Trail, Milwaukie, OR

Back to Oregon

We returned to Oregon after moving two and a half years ago. We are staying in a cute Airbnb downtown Oak Grove, near Milwaukie, OR. It feels great to be back!

Family and friends are within half an hour’s drive. I am looking forward to seeing them. The Max Light Rail is a mile away, so I will plan a visit to downtown Portland. 

Walking The Trolley Trail!

However, the most compelling reason we picked this Airbnb is the Trolley Trail, located just around the corner. This allows us to run or walk before we socialize with friends.

Wednesday, December 14, 2022

While hubby ran on the Trolley Trail, I brought my camera and walked the trail to Milwaukee. The weather drastically changed compared to the week before. I wore my winter coat, gloves, and several layers of clothes to keep warm. I don’t remember it being so cold when we lived here.

Thursday, December 15, 2022

Our oldest son visited for coffee and lunch. He arrived early because he had to work again in the afternoon. We set out for an early walk on the trail, bundled up to stay warm in freezing temperatures.

Saturday, December 17, 2022

Hubby and I stretched our legs after lunch. We walked the trail south to Gladstone. During the other walks, we had not seen many people enjoying the track, but due to a beautiful sunny day, many people cycled, ran, or walked the trail.


Sunday, December 18, 2022

A gorgeous afternoon for a long hike. I walked to downtown Milwaukee. The beautifully carved sculptures along the trail never get boring.

Monday, December 19, 2022

After we ate our delicious homemade quiche for lunch, we walked to Gladstone to burn off the extra calories. 

Once the Portland Traction Company’s Oregon City Line streetcar ran between Milwaukie and Gladstone from 1893 until 1968. Today, its rails are removed and the line is converted into the Trolley Trail. Only six miles, from Milwaukee to Gladstone, of the planned 20 miles are completed. In the future, the trail will connect Portland, Oregon City, and Gresham as well.


Several in December 2022


4.50 miles

Moving Time

1.5 hours


freezing, chilly, cloudy, sunny