Sweet Escape: Drive-By Adventures in the City

It’s Drive By Time — a lighthearted neighborhood photo tour. I had so much fun taking these pictures; it had been far too long since our last Drive By neighborhood tour. I hoped you felt like you were riding along with me, admiring each house. Some shots were tricky: many homes are tucked behind gardens, gates, fences, dense shrubs, and yes, the occasional guard dog. My husband drove while I photographed, which made the adventure both safer and more efficient.

I may have been a bit daring for some of these photos, so forgive the slightly crooked or soft images. I was often crouched in rose bushes or darting out from hedges to catch a view before someone noticed. You learn quickly how odd it can look to leap from shrubbery when surprised dog walkers pass by. All part of the unpredictable world of drive-bys.

Fasten your seat belt — the first cluster of houses is in the Irvington and Grant Park area of Portland. These homes are more exposed to the street than others we visited later, so there were fewer obstacles. I loved the cottage with the purple door and trim — I found myself gravitating toward Tudor-style details throughout this tour.

Notice the charming downspout detail — no ornament too small.

We then crossed the river to the west side of town and explored Dunthorpe, a lovely, older neighborhood not far from where I live now. My parents once lived here, and it remains one of my favorite areas to wander because the homes are authentic, stately properties with a sense of privacy and legacy rather than oversized showpieces.

One house in Dunthorpe required a bit of daring: I crawled through front-yard bushes just to glimpse the backyard. Once through the shrubs I was rewarded with a stunning view—so inviting that I practically ran across the lawn toward the outdoor fireplace, which explains why that image turned out a little blurry. My husband called me back before I got too adventurous: “Meli? Meli?! Where are you?” So I had to return to the car, though I managed a quick snap of the neighboring property before we moved on.

After that stunt my husband insisted I stay in the vehicle for the rest of the tour. He joked about leaving me in the shrubbery next time — he was a little embarrassed by my stealthy behavior.

One of my favorite photos was taken while hanging out the car window. This house felt like a fairy tale, with lights in the front window and a beautiful gate that gave it a storybook charm. Many properties had gates locked, a reminder that privacy is important to these homeowners and that drive-by viewing sometimes means appreciating details from the street or car.

Another home sat in an especially picturesque setting that my camera struggled to fully capture. The landscaping and setting were dramatic, and we even discovered a surrounding water feature when we backed up too close — a brief awkward moment that signaled it was time to leave the neighborhood before we overstayed our welcome.

I have more pictures to share from other neighborhoods, but they will have to wait for another Drive By. Thanks for joining this tour — I hope you enjoyed the peek at these beautiful Portland homes. If you missed the first Drive By from October 2007, you can find it on the blog archive referenced previously.