Back to the 50s: A Walk Along Upper Sandy Boulevard in Portland

Enjoy a walk through Portland's 1950s history along Sandy Boulevard

From a Catholic garden sanctuary to a former racist restaurant, Sandy Boulevard in Portland offers a look into Portland's recent history. Read my full review with what to see and where to eat on Sandy Blvd. after the break.



This is a walk we found in Walking Portland, an excellent book with many historic and interesting walks in Portland.

Sandy Boulevard in northeast Portland cuts through the Hollywood district and continues on through part of Portland that really built up during the 1950s. The automobile had a big influence on the history which you can see from the wide boulevard and types of diners. But the area has seen better times, although there is still history and things to see here. And you won't go hungry!

The walk is about 2 miles (each way) and it's slightly uphill. If you decide to walk around The Grotto, be sure to add in another mile or 1.5 miles. It took us about three hours for the round trip walking, including time at The Grotto.

Walking Upper Sandy Boulevard on Google Maps

We parked near Clyde's. There are some nice homes and plenty of residential parking.

Clyde's Prime Rib
Clyde's Prime Rib has a colored past (it was a 50's chicken joint with a racist name and logo -- more info here)

Fire Station 28
Built in 1913 and recently renovated. The statue is named Araminta after Harriet Tubman's birth name.

BTU Brasserie
BTU Brasserie is one of the new brew pubs and restaurants along upper Sandy Boulevard. 

Pho An Sandy
Pho An Sandy is one of many Vietnamese and Thai restaurants to be found.

Annie's Donuts
Annie's Donuts was a delightful surprise, and it came just in time as we needed a little snack to keep up our energy for the rest of the walk. In fact, Annie's Donuts turned out to be our favorite donut in Portland. (We ate plenty of other donuts too -- see my list of Best Portland Doughnuts.)

Fairley's Pharmacy
Fairley's Pharmacy is just across the street from Annie's Donuts in a wedge-shaped building that still serves soda fountain drinks. It was seen in the movie Drugstore Cowboy. TIP: Keep an eye on the crossing signals if you walk across the street here, as there several intersecting streets with a lot of fast-driving cars.

Roseway Theater
Roseway Theater still shows first-run movies.

Mural seen from Sandy Blvd.

The Sandy Jug
There once were many buildings on Sandy Blvd. built to look like what they sold. 

The Sandy Jug is now Pirate's Cove (a strip club).

The Grotto
The Grotto is a Catholic church with many statues placed throughout a large garden. It's open to the public. 

Upper level of The Grotto
Buy a ticket for the elevator, and go up 110 feet to The Grotto's upper level. There you will find a garden sanctuary where you can walk among the trees and flowers as you contemplate God in nature. We spent at least an hour there and it was wonderfully relaxing.

TIP: I suggest taking the walk in the reverse order as described in the book. That way, you can start at The Grotto, and end about half way at which point most of the sights have been seen. You only need to drive down to the firehouse if you want to see its statue, and Clyde's.