Two Nights in Portland, Oregon – May 2025

Two nights in Portland: Bypassing Tillamook and taking the road less travelled to Oregon’s capital, Portland; desolation in downtown Portland; more trams than people, and a weird weather machine; hanging on grimly: hurrah for Zara; Oregon Maritime Museum, closed as usual; the kindness of cabbies; Elon doesn’t care, but Uber does; dinner at Huber’s; Washington Park and Nob Hill; fragile waiter at Andina restaurant, saving us a trip to Peru

Having spent two nights regrouping and doing laundry at Oceanside (click here), we drove the rental car up the road to Tillamook, home of a famous cheese factory. (Interestingly, or perhaps not, ice cream from the Tillamook Creamery, which is part of the factory, is available in Australia from Woolworths.) The factory only opens to visitors at 10am on a Monday, which was too late for us, sadly; Roy had planned to return the car by 11am.

There were two possible routes to Portland. We chose the northern one, Route 26 (Sunset Highway), which winds spectacularly through national parkland forests, to reach the capital of Oregon in just over an hour and a half.

Two Nights in Portland’s Harlow Hotel

As you can see from the pictures and the blurb in the poster below, Harlow Hotel (built in 1882) in Portland’s Pearl District has been sympathetically restored and redeveloped in our beloved Art Deco style. Taking into account the bare-bones room amenities, palpable under-staffing and minimalist service, I would give it a 3/5.

 

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Day 1: Desolation in Downtown Portland

After dropping off the luggage at Harlowe Hotel and returning the rental to the nearby Avis, we took a walk down to Pioneer Square in the central business district.

Two Nights in Portland

I wanted to see the famous Weather Machine in Pioneer Courthouse Square (below) do its regular noon weather forecast. What a peculiar device! Coloured lights flash, there’s a trumpet fanfare, and then this bronze sculpture spits from the top of its head one of three designs: a sun for clear weather, a blue heron for drizzle, or a dragon for rain or storms.

Tell me what you think this emblem (at top left, on top of the device) represents: a sun, a heron or a dragon? Because it rained much of that afternoon and evening, and was fully cloudy the next day.

The Weather Machine in downtown Portland

Weather is a preoccupation in Portland, as in so many other places that lack and long for sunshine. Locals expect it to be rainy, said Kirby, the Uber driver who took us to Washington Park the next day; it wouldn’t be Portland if it didn’t rain. And, he added, if you’re going to be caught in the rain, it might as well be in a beautiful place like Washington Park.

Here’s a cheery photo of a nice blue tram, taken during a brief lull in the Portland rain

Even apart from the weather, downtown Portland is not a beautiful place. The central business district – and you can’t use the acronym CBD anymore, because nowadays that almost universally means cannabidiol, and there’s a cannabis shop on just about every corner – is in a torpor. Low business occupancy levels means deserted streets and a distinct absence of office workers, even at lunch-time.

The main reason? Portland’s ongoing drug and homelessness crisis, along with vandalism, theft and violence. (More on this later.)

Hurrah for Zara and Din Tai Fung!

Adjacent to Pioneer Square is shopping mall Pioneer Place. Hurrah for Zara!, I thought. Most of the shops were vacant, however – the only others of possible interest to me were Nike, Mango and H&M.

Pioneer Place, shopping mall in downtown Portland OR with just a handful of tenants

We did, however, have a late lunch at Pioneer Place’s Din Tai Fung, the Taiwanese chain that’s our favourite dim sum eatery in Singapore. And it was outstanding!

Dim sum lunch at Din Tai Fung: beef tendon soup and xiao long bao

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Portland Waterfront

Thus fortified by hearty beef tendon soup and xiao long bao, we walked down to the Willamette River and the waterfront. Good thing we hadn’t set our hearts on visiting the Oregon Maritime Museum – located on this fully operational paddle-steamer, Str Portland, a sternwheel towboat built in 1847 – because it was closed.

Portland Maritime Museum – presumed to be open sometimes, but not on this Monday afternoon*
  • Seems the Oregon Maritime Museum is open from 11am to 4pm on Wednesdays, Fridays and Saturdays. That’s rather sad.
Str Portland, home of the Oregon Maritime Museum and moored on the Willamette River

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Miserable homelessness

Many dead, tonight it could be you
And we are homeless, homeless
Moonlight sleeping on a midnight lake

Homeless, Paul Simon with Joseph Shabalala and Ladysmith Black Mambazo (1986)

Turning left, we headed towards the Pearl District and Portland’s Union Station, to check where we’d be catching the Amtrack train to San Jose, California a couple of days later.

Soon, the extent of Portland’s homelessness became shockingly evident. Tents and other makeshift shelters crowd the doorways, pavements and parks. The misery was almost palpable, mental health problems and drug addiction evident everywhere. One young woman was stripped to her lilac underwear in the middle of a cold, wet pavement, contorted like a pretzel while injecting something between the toes of one of her filthy feet. Several other unfortunates lurched blindly around.

Of course I’ve seen homeless people, but nowhere near to this scale. That walk to the station, and back to the hotel, was genuinely distressing. I knew I wouldn’t be doing my usual solo strolls around this failing city. Though I couldn’t bring myself to photograph what we saw, you can click here for hundreds of images of the homeless and drug-addicted in downtown Portland.

2 days in Portland
Union Station, Portland OR

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The Kindness of Cabbies

I have often relied on the kindess of strangers.

Blanche du Bois, a character in Tenessee William’s play A Streetcar Named Desire.

According to the Uber driver who later drove us to dinner at Huber’s, there is not more but less homelessness here now than was the case a couple of years ago.

I liked this driver: when his Tesla asked us to do up our safety belts, Roy said he’d do it for Elon. The driver replied: “Elon doesn’t care, but Uber does.”

He also told us that:

(a) No locals come to downtown Portland anymore;

(b) Locals don’t patronise the guidebook-vaunted chain store Voodoo Doughnut, click here, with its weird and wonderful flavours; they prefer Blue Star Donuts, which when it sells out around 11am or noon will simply close shop (click here for a review of Blue Star’s Cointreau crème brûlée doughnut);

(c) Given our two days in Portland, he suggested visiting Washington Park tomorrow. So that’s what we did. I find that you seldom go wrong with advice from a cabbie.

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Dinner at Huber’s

We loved Huber’sPortland’s oldest bar and restaurant, established in 1879 as The Bureau Saloon. It’s all high ceilings, low lighting, original wooden panelling, intimate booths and a long bar with overstuffed bar-stools.

Old-fashioneds at Huber’s bar, Portland OR

In 1880, James E. Pepper of Louisville, Kentucky, is said to have been the inventor of the Old Fashioned, one of Roy’s favourite cocktails. This Prohibition-era mix of bourbon, bitters and orange peel can be delicious, and this one was definitely the most delicious I’ve tried… chilled with a single large ice cube stamped with the Huber’s logo.

An old-fashioned, complete with logo-ed ice cube

Recipe for an old-fashioned

It is described on the drinks list as: “2 oz of Old Forrester bourbon, simple syrup, a few dashes of Angostura bitters, stirred and poured over a large, logo-ed rock. Garnished with an orange peel and a cherry.”

Though it has a range of other menu items, Huber’s has always been famous for its turkey dinner. I don’t even bother with turkey at Christmas, but this seemed a good time to make an exception. Roy and I both ordered the half-and-half – half turkey, half ham – which came with gorgeous stuffing, yummy gravy, tender broccoli and yam (sweet potato) or mash. An Oregon chardonnay went perfectly with the tastiest, most succulent turkey I’ve ever eaten, and I couldn’t resist polishing off both my and Roy’s cornbread and butter.

Half-and-half roast turkey and ham at Huber’s, Portland

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“The creatures looked from pig to man, and from man to pig, and from pig to man again; but already it was impossible to say which was which.”

1984, by George Orwell, 1949

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Day 2

Washington Park

Following Uber-driver Kirby’s suggestion yesterday, we took another Uber to Washington Park’s Japanese Garden. Unfortunately, it’s closed on Tuesdays. Hmm. We didn’t bother to visit the famous Rose Garden, as Kirby had informed us that the roses were not yet in bloom. (He’d just taken his mum there for Mother’s Day.)

Washington Park, Portland
Washington Park, Portland

Luckily, Washington Park offers a free 30-minute shuttle ride around the park, stopping at the Rose Garden and various other highlights. These  include Hoyt’s Arboretum, Oregon Zoo, a Holocaust Memorial, an archery range, tennis courts and more.

Disembarking from the shuttle at the park entrance, it was a longish but gentle walk through Nob Hill and adjacent neighbourhoods back down to our hotel. That walk showed us a more gracious side of Portland.

Terrace houses in NW Glisan Street, Portland
Pet supply shop?
Keen, a footwear and accessories shop in the Simon Building in Portland’s gentrified 13th Avenue Historic District
No, no, no – Pharmacy is in fact a club!

Many of the upmarket restaurants, elegant shops and chi chi delis bore signs supporting Rose* Haven (click here for more), which, for the past 28 years or more, has been providing “day shelter, resources, emotional support, and community connections” to women and children experiencing homelessness and poverty. We passed its HQ on our way, with volunteers actively receiving community donations on the pavement.

* Rose City is Portland OR’s nickname, by the way.

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Dinner at Andina

On another recommendation from Kirby, we had booked at Andina, an upscale Peruvian restaurant in Glisan Street just a seven-minute walk from our hotel. I wasn’t expecting such a large, glossy interior – and it was packed to the gills.

Peruvian cocktails at Andina – on the left is Roy’s pisco sour; I’m hoping that wasn’t a cockroach in my tupananchiskama

It was tasty and interesting food, and now we don’t have to go to Peru, says Roy.

It took a while to fathom the Spanish-heavy menu, but we got there. From the list of “cocteles”, Roy had a pisco sour; I had the memorable yet unpronounceable tupananchiskama (illegal mezcal, Peruvian pepper-infused Aperol, averga, lime and amargo chuncho*). Most of the menu items were listed in this awkward way.

*If you absolutely have to know, amargo chuncho is Peruvian bitters.

There are only so many times you can look up the Spanish ingredient online, and only so many times you can ask your fragile waiter to translate from under his trembling, supercilious little moustache.

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For starters, roasted beef heart on skewers (anticucho de corazón) came with finely sliced red onion, crispy potatoes and salsa criolla; the divine Oregon lettuces was a salad that included local strawberries, mint, cheese, pecan-corn crunch and a green garlic-huacatay dressing. It was delicious.

We shared a main course of lomo saltado,* tasty steak wok-fried with tomatoes, onions, soy sauce and ginger, combined with French fries and served with rice on the side; plus a yummy side dish of fried cassava cakes with two dips. So, now we know about the significant Chinese influence on Peruvian cuisine that has resulted in a fusion known as chifa.

Note on the lomo saltado: Just because one can stir potato fries into a beef stir-fry, does not mean that one should.

Speaking of Spanish, Spanish-speakers represent a large percentage of the population. I wasn’t expecting that up here in the northwest corner of the USA. I had assumed immigration, and yes, Hispanic and Latino populations have grown by 30% in the past decade. AI opines that the significant presence of Spanish speakers in Portland developed largely due to 20th-century migration patterns. These included the massive Bracero Program, a temporary labour initiative that allowed Mexicans to be employed in the US agricultural and railroad industries from 1942 to 1964.

“I’m a very rare sort of bear,” he replied importantly. “There aren’t many of us left where I come from.” “And where is that?” asked Mrs Brown. The bear looked round carefully before replying. “Darkest Peru.”

A Bear Called Paddington by Michael Bond, 1958

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Up Next?

All aboard as we take the overnight Amtrak train from Portland south to San José CA, where we start another road trip: down the Pacific Highway to Newport Beach!

 

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Verne Maree

Born and raised in Durban, South African Verne is a writer and editor. She and Roy met in Durban in 1992, got married four years later, and moved briefly to London in 2000 and then to Singapore a year later. After their 15 or 16 years on that amazing island, Roy retired in May 2016 from a long career in shipping. Now, instead of settling down and waiting to get old in just one place, we've devised a plan that includes exploring the waterways of France on our new boat, Karanja. And as Verne doesn't do winter, we'll spend the rest of the time between Singapore, South Africa, Australia and New Zealand - and whatever other interesting places beckon. Those round-the-world air-tickets look to be incredible value...

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