It’s Drive-By Time! I’m excited to share another neighborhood tour — it had been far too long since our last drive-by. I had a blast taking these photos and imagining you riding along with me, admiring the architecture. Some shots were a real challenge: many homes are tucked behind gardens, gates, fences and hedges, and occasionally guarded by dogs. Thankfully my husband drove while I took the pictures, which made the whole adventure a bit easier.
I’ll admit some images are a little crooked or slightly out of focus — I was sometimes squeezing into shrubbery or crouching behind hedges to avoid being noticed. There were moments when I had to shoot and run, which can look odd if you leap out of a bush and surprise a dog walker. These awkward little episodes are all part of the drive-by experience.
Fasten your seatbelts — we’ll start in the Irvington and Grant Park neighborhoods of Portland. These houses sit more openly than others we visited, so we didn’t face as many obstacles getting photos. I was especially drawn to the Tudor-style homes and charming details like the purple door and trim on one cottage. Small flourishes make these houses memorable.
Not to be overlooked — even the downspouts get attention here.
Next we crossed the river to the west side and drove through Dunthorpe, a stately old neighborhood not far from where I live now. It’s one of my favorites for drive-bys: the homes aren’t new showpieces but genuine, historic residences owned by people who value privacy and understated elegance. I plan to show my parents’ former home in a future tour — I somehow forgot to photograph it this time.
The next property was the one that had me crawling through front-yard bushes just to glimpse the back. I risked a bit of embarrassment and a prickly hedge or two, but the view was worth it. Getting closer revealed a breathtaking outdoor fireplace and a lawn that felt made for gatherings. I was so eager to explore that I actually sprinted across the grass to get nearer — hence the slight blur on that photo as I dashed forward.
My enthusiastic sprint paused when my husband called from the car, reminding me I couldn’t stray too far. He insisted I stay close for the remainder of the visit, threatening to leave me behind in the shrubbery if I tried any more daring escapes. After that, most pictures were taken from the car window while he kept a watchful eye.
Even from the passenger seat I found a few favorites. One house felt straight from a fairytale with soft lights in the front window and a beautiful iron gate — the kind of place that makes you slow down and imagine life inside. Many properties keep gates locked, a sign of the owners’ desire for privacy and quiet.
One striking home sat in an especially picturesque setting with sweeping landscape and a water feature that reminded us of a moat. That particular property even had us backing the car up carefully — another slightly awkward but memorable drive-by moment that made us chuckle and decide it was time to move on.
I have more photos to share from this outing, but they’ll wait for another drive-by installment. Thanks for coming along — I hope you enjoyed this glimpse of Portland’s charming neighborhoods as much as I enjoyed capturing them.
Thanks for joining me! If you missed the first Drive-By from October 2007, refer to the original post for more neighborhood inspiration.