Portland: Weird, Wild and Wonderfully Delicious
We rolled out of Olympic National Park at sunset, waved goodbye to the Tree of Life and Kalaloch, and drove through the night looking for lodging, town after town-No Vacancy. By 11pm we landed in a really cool place, Olympia, where we finally crashed and slept like royalty.
The next day was all about decompression. Lunch at Row on the Harbor: artsy, hip, and so good we decided to stay another day. The next day early dinner at Anthony’s—a little more polished, very pretty spot, continental-leaning, but equally swoon-worthy seafood. A little R&R after 26 straight days of road-warrior pace. Next, Oregon was calling: part reunion tour with friends, part “Portlandia” pilgrimage, part mission to fix poor Bessie’s cracked windshield (Olympic Park’s parting gift).
Basecamp Beaverton
Seattle had been a parking nightmare for the van, so Alan said No Portland and took over hotel-duty and scored big. Beaverton’s Hilton Garden Inn—tech-hub adjacent, Hilton Honors perked. Surface parking for Bessie, clean sheets, and a bar. Win.
Game plan: downtown Portland wander, waterfall chaser, Mt. Hood teaser. Oh, and friends scattered across coast, city, and mountains. A choose-your-own-adventure in weird.
Day 1: Portland District Dive
Portland isn’t one big city—it’s like six little enclaves that all got together and decided to out-quirk each other:
Pearl District: Artsy, industrial-chic lofts, Powell’s City of Books (book nerd nirvana), indie galleries, and yes—Voodoo Doughnuts if you want pink boxes and neon sugar highs.
Old Town/Chinatown: Gritty, historic, home of Lan Su Chinese Garden (a serene oasis plunked into chaos). Saturday brings an open-air food-cart bazaar.
Downtown Core / Cultural District: Portland’s buttoned-up cousin—museums, theaters, and the rare spot where you might put on a blazer.
West End: Hip boutiques, vintage shops, indie designers, and Blue Star Doughnuts (the “gourmet” cousin to Voodoo-the maple glazed was yummy).
NW 23rd / Brewery Row: Craft beer, cocktail dens, distillery row—pick your poison.
Hawthorne & Belmont: Vintage thrifts, tattoo parlors, incense-heavy record shops, rainbow murals. Portland’s counterculture heart still thumping.
Our Stroll: Books, Blossoms & Bessie’s Break
First stop: Powell’s. The largest indie bookstore in America—multiple floors, endless rooms. I made a beeline for “Travel Writing (not guidebooks)” and imagined my future book nestled there. (Powell’s confirmed I’d also fit under Americana or National Parks. Shelf goals achieved!)
We aimed for Voodoo Doughnuts but were waylaid by encampments and confusion—sometimes Portland’s contradictions hit hard. From there we drifted into Chinatown and the Food Cart area (again, heavy on tents and grit). A quick retreat into Lan Su Chinese Garden reset the vibe: quiet courtyards, koi ponds, and the best iced jasmine tea I’ve ever had.
Kodi patrolled like a pro.
After the downtown swirl, we swapped skyscrapers for hillside estates: Japanese Gardens (no dogs, multi-level, beautiful but off-limits for our crew), Rose Test Garden (jammed, no parking), and then the gem: Pittock Mansion.
Mr. Pittock—newspaper baron, mountaineer, mansion-builder—apparently climbed Mt. Hood four times (note to self: no excuses). His estate is all roses, hydrangeas, and towering firs. The hazy skyline teased Mt. Hood in the distance.
We capped the day at Council Crest Park, the city’s highest point. Think cyclists, off-leash dogs, picnic blankets, and sweeping views of the Cascades. A perfect Kodi run. Dinner back in Beaverton at Frank’s Noodle House—slurpy, spicy, totally worth crossing the river for.
Day 2: Waterfall Wonderland
Waterfall chasing is practically a religion here, and the Columbia River Gorge is the temple.
Multnomah Falls: the icon—two-tiered, dramatic, everyone’s screensaver.
Horsetail Falls: slender, elegant, tucked in the greenery.
Latourell Falls: basalt amphitheater walls, power and spray.
Bridal Veil Falls: tucked away but worth the detour.
The drive along Highway 30 is a loop-de-loop of mossy cliffs, sheep farms, and little moments that feel like postcards.
We got greedy and aimed for Silver Falls State Park—the “10 waterfalls in one hike” Insta-famous paradise. Except: it’s two hours southwest, edging into the Willamette Valley wine country. Gorgeous drive past Parrett Mountain Vineyards, but not exactly next-door.
We parked at North Falls, map in hand, pine-scented air filling our lungs. Alan bowed out early. Kodi and I pressed on: first the overlook, then the steep Rim Trail (too rocky for her paws), then Twin Falls Trail (too steep for my knees without poles). Every direction: a “nope.”
Sometimes you get the waterfall. Sometimes you just get the journey.
Alan, ever the realist: “You got Multnomah. Can’t top that. Was it fun?”
Me: “Yes. And I burned off all those restaurant calories. Call it even.”
Day 3 – Van Drama, Shining Memories, and Mt. Hood Magic
Day three started with van drama. Cracked windshield , now diesel fumes, a suspicious fuel leak—basically Bessie (our beloved van) auditioning for a soap opera. Alan, ever the practical one, declared:
“We have to fix it here so it doesn’t blow out in the middle of nowhere!”
Which meant my much-anticipated Mt. Hood hike had to wait. Nervous energy + a delay = me spiraling down the internet rabbit hole of trail names that sounded like fantasy novel characters: Silcox, Parker, Magic Mile, Glacier Overlook. Was I heading to Mordor or just up a mountain? Hard to tell.
Most hikers stick to the Timberline Trail circling the base, or the wildflower-filled Meadows. But I had one goal: go up. Straight up. Common sense (and the Timberline Lodge webcam) said it was just a steep, snow-free grind until the glaciers. No spikes on my shoes, no technical gear; but hey, no excuses either.
Alan had the coffee waiting when I rolled out of bed at 4 a.m., and by 6:15 we were pulling into the lodge parking lot: already slammed full. (Apparently half of Oregon had the same sunrise idea.) We squeezed into a spot, I waved goodbye, and followed two hikers up the trail.
The Climb
Bam! Within ten minutes it felt like getting sucker-punched in the lungs. Steep doesn’t even cover it. Out came the walking stick, and I clung to it like a cane-wielding mountaineer. A friendly hiker descending told me, “There’s a picnic bench up at Silcox.”
Picnic bench? That became my holy grail. I powered up through heavy breathing, photo stops, and pep talks until finally…Silcox Hut and its humble wooden bench appeared like an oasis. I plopped down, joined by a couple who looked equally relieved to be horizontal.
From there, the summit loomed, glaciers glinting in the morning sun. Could I go higher? Maybe. But without crampons or a death wish, I called it. I had what I came for: the sweat, the grind, the sunrise views, and the bragging rights.
By 10 a.m. I was back at the trailhead where Kodi (tail wagging) and Alan (coffee refilled) greeted me like a conquering hero.
The Shining & a Margarita
Before leaving, I ducked into Timberline Lodge—the one immortalized in The Shining’s aerial shots. Inside, it’s all massive beams, stone fireplaces, and slightly spooky vibes. I found the axe from the Overlook Hotel, snapped a picture, and treated myself to a mountain-top margarita. Because nothing says “serious mountaineer” like tequila at altitude at10am.
Trillium Lake & Fruit Loop
Next stop: Trillium Lake. A sapphire pool at the foot of Mt. Hood, it was buzzing with life—wakeboarders, kids splashing off inflatable rafts, kayakers, fishing lines zipping; all framed by Hood’s perfect, snow-capped triangle. The scene was pure Oregon postcard.
From there, we rolled onto the Fruit Loop—32 miles of orchards, lavender farms, country stores, and wineries. Think Norman Rockwell with a hipster filter. We grabbed apple milkshakes (amazing), skipped the wine (too sticky with diesel fumes in the van), and reluctantly headed back to Beaverton to figure out how to fix Bessie’s mysterious leak on Labor Day weekend.
Because of course.
But here’s the thing: van chaos makes for the best stories—as long as it gets fixed. Next stop: camping on the coast!