Was there ever a hotel as ace as the Ace? In my first visit to Portland, Oregon I revelled in its grungy quirks (even the vintage shower that didn’t work). With master mixologist Jeffrey Morgenthaler and definitive Stumptown Coffee on the premises and the legendary Powell’s City of Books two blocks away who could ask for a better base in this playful, radical city George Bush dubbed ‘Little Beirut’?

I swore this would always be my Portland lodging of choice. And the vow stuck – until six months later, stopping off on a San Francisco-Seattle road trip, I discovered Jupiter. Not via any space shuttle, simply by crossing the Burnside Bridge into a post-industrial quarter that’s on the up from a long way down. In this process the Jupiter Hotel and its in-house  live music venue, the Doug Fir Lounge, have been a major catalyst, along with Portland’s top restaurant Le Pigeon next door and Burnside Brewing Co across the road. Good things come in clusters.

We had been asked when booking the Jupiter, a converted motel, whether we preferred a room on the Bar Side or the Chill Side; the former giving you an up-close share of party central until dawn, the latter offering a chance of some shut-eye. We chose Chill, taking advantage of an extremely comfortable bed in a compact but murally soothing environment.

Host to many top acts, the Doug Fir Lounge has regularly been named one of America’s premium gig venues – and there’s strong competition in Portland itself from the likes of Mississippi Studios and the Crystal Ballroom. Indeed the Jupiter’s leaflets claim 12 music venues within a mile radius (along with five distilleries within two miles and award-winning breweries four blocks) We just loved the timber-clad Doug Fir’s happy hour bar vibe, the raucous stand-up getting the party under way and then the fire pit bonhomie of the joint.

The beer was better, though, at Burnside Brewing and we couldn’t resist taking in Le Pigeon, 30 seconds round the corner. I’ve been cooking from restless pioneer Gabe Rucker’s cookbook for several years and the bistro didn’t disappoint with dishes such as caraway crusted sweetbreads; foie gras thom kha; and truffled chicken, shrimp and grits, corn succotash, prawn-tarragon aioli. Top end prices, especially for wine, belie the casualness of the setting and make it a special occasion place.

A more accessible and affordable bet for a Jupiter guest is three minutes’ walk away on S.E. Alkeny Street – a cafe outlet from street food champion Nong’s Khao Man Gai, whose original food cart is still serving its trademark poached chicken with rice downtown on the corner of SW 10th Avenue and SW Alder Street. Sunday Times restaurant critic Marina O’Loughlin is a big fan.

Street food ‘pods’ are scattered around a city devised on a grid system (hence NE, NW etc attached to some impossibly long streets to signify which district you are in). The corner of 28 South East Place and Division Street hosts the Tidbit Food Farm and Garden, a lovely place to refuel, global food carts circling the Scout Beer shack like covered wagons. 

Bibimbap, sushi, roasted pepper tri-tip, Fillipino pork stew – it’s a dazzling Asian road trip. Alternatively, there’s Texas brisket or candied bacon burgers, waffle sandwiches and wood-fired pizza. I grabbed a picnic table, a Fresh Hop Simcoe brewed by the hyperactive beardies at Breakside and slurped the best bone stock rich ramen I’ve ever eaten from a truck called Hapa. The name describes the fusion of Japanese cooking techniques and Hawaiian recipes. For a full of Portland’s food cart locations visit this link.

Though Seattle would claim the honour, sometimes you feel Portland invented coffee, too, it’s home to so many acclaimed roasteries. Stumptown is the place to start. It took on the city’s nickname (from its logging past) and for nearly two decades this roastery has set the standard by which rivals are judged. These are many to pick from nowadays. Take Extracto , a decade-old chain of two with its roastery at the original N.E. Killingsworth Street cafe/shop. From the Eleven of Spades house-blend through rare single-origin roasts to the elevation of latte decoration to an art form it hits all the right coffee buttons.

With all this coffee, well, you’ve got to have a doughnut. Jupiter does a ‘The Magic is in the Hole’ certificate for guests, providing a ‘Voodoo Dozen’, a pink box of 13 from the city’s most hyped provider. Voodoo even run to a Homer Simpson tribute doughnut (creator Matt Groening is a Portlander and several of the cartoon’s characters are named after its streets – Ned Flanders, Milhouse and the like). 

Locals insist  Blue Star is the hipster doughnut of choice. I understand why when I scoff one of their lauded creations – a riot of intense chocolate, cream and brioche. The wonder of it is captured fully in a local website’s Deconstructing Blue Star’s Valrhona Donut. I’d checked out their Mississippi Avenue outlet en route for a Brewvana craft beer walking tour. 

This vibrant corner of town, once a no-go area now on the cusp of gentrification, has lots to offer – the aforementioned Mississippi Studios, a street food pod (naturally), a cannabis store and the amazing Paxton Gate offering stuffed animal collectibles – but its breweries are worth the trip alone. Our ‘Brewvana Mississippin’ tour guide April took us around three, Ecliptic, Stormbreaker and Hopworks Bike Bar and what our small party tasted along the way, especially at the latter, revealed why Portland contends with Denver for the title of US Capital of Beer. The three hour tour costs $69 and you do get to eat the pretzel necklace that brands you as an ale geek.

Of course, the intoxicant of choice is not always malt and hop-driven. ‘Keep Portland Weird’ says the parking lot sign opposite Voodoo Doughnuts. Personal consumption of cannabis is legal in Oregon; still I resisted the temptation in its largest city to get high on a brownie infused with the stuff. They even sell ready-rolled joints in specialist dispensaries such as Nectar.

Oh and salt is more than a footnote if you visit Mark Bitterman’s two sodium chloride-centred delis called The Meadow. Conveniently, one of them is up on resurgent North Mississippi Avenue next door to a Blue Star cafe. It was here I bought kala namak (Himalayan black salt) and a couple of Bitterman’s books – one on salt naturally, the other on cocktail bitters.

In it he name-checks another Portland legend, Jeffrey Morgenthaler, mixologist at Ace Hotel’s Clyde Common bistro and Pépé le Moko speakeasy. I couldn’t resist begging this  cocktail high priest for one of his celebrated barrel-aged Negronis.

Post Negroni (or three) for further weirdness walk up to 901 Salmon Street and gaze up at a whole salmon swimming through the corner of a brick building. It’s an 11ft long bronze sculpture called Transcendence, high above a seafood restaurant.

The city hosts some of the most inventive street art around. Some of it had rubbed off in my room at the Ace, adorned by a giant cat image guarding my personal vinyl deck. Retro touches extended to a Heath Robinson-like steel shower in my standalone tub that I gave up on and recycled fabrics and furnishings I found charming if hardly luxurious. Downstairs, though, oozes sociable cool. Check in and you may never leave. Unless Jupiter is in your orbit, dude.

For something different to enliven your stay in this most civilised of American cities in bewildering times check out these five fun options:

1 Small is beautiful at Leprechaun Park

Mill Ends Park – total area 452.16 sq in – holds the Guinness World Record for the world’s smallest park. Known as Leprechaun Park, it fills a circular concrete hole, once meant to be the base for a lamp-post on Naito Parkway. Back in the 1940s a local journalist, whose office overlooked it, decided to plant flowers there and it was officially recognised as a city park on St Patrick’s Day 1976. PS Don’t aim to spend a whole day there. 

2 Or if you fancy a more expansive green escape

The formal Japanese Garden has now added an extra 3.4 acres to its original 5.5, featuring ornamental cherry trees, ponds and tea house. The revamped Cultural Village has an authentic style medieval castle wall, which was built with traditional hand tools under the watchful eye of a 15th-generation Japanese master stone mason. It’s a place of tranquil contemplation all year round but must be spectacular in blossom season.

3 Portland’s Chinatown

Once dubbed ‘The Forbidden City of the West, it is now much diminished. The opium dens, brothels and kidnappings via the ‘Shanghai tunnels’ to the riverside are now gone, but the area retains a certain seediness. All the more surprising to stumble upon the gorgeous Su Lan Chinese Garden, which occupies a whole city block on NW Everett Street. Modelled after Ming Dynasty gardens and built by Chinese artisans from twin city Suzhou, it offers a microcosm of Chinese culture. Taste the tea, feel the harmony. A Portland must.

4 A good bookshop? 

Look no further than one of America’s largest, offering used and new – Powell’s City of Books. On West Burnside Street around the corner from the Ace and boasting a spectacular wine and cookery section, I couldn’t resists its allure. After three Powell’s trips my Delta baggage allowance was in serious danger.

5 Wine? Head south to the Willamette Valley

Portland has its own urban wine scene, but the real deal is less than an hour away. Willamette is famous worldwide not for being Portland’s river but for being focus of the Oregon wine industry. Roam the hills around Newberg, Dundee and McMinnville 30 miles or so south of Portland. You’ll receive a warm welcome at any number of folksy family wineries. To plan an itinerary visit this link. We went upmarket to Ponzi, one of the pioneering wineries created by ‘escapees’ priced out of California and seeking a fresh terroir for the Holy Grail grape, Pinot Noir. That was 45 years ago and nowadays the luxurious tasting room and terrace overlooking the Chehalem Hills vineyards feels not a million miles from Napa. Accordingly, a single flight featuring a selection of current vintages costs $20 with cheese and charcuterie plates from $12. Worth splashing out for wine and setting. The winery has recently been bought by Bollinger.

Fact file

Factfile

Neil Sowerby stayed at The Jupiter Hotel, 800 East Burnside Street, Portland, OR 97214 and at the Ace Hotel, 1022 S.W. Stark Street, Portland, Oregon 97205.

The Covid pandemic has grounded most of the transatlantic air services, but as lockdown ends expect a resumption from the like of British Airways and Delta.

An essential guide to the area is Travel Portland. For further afield in the state go to Visit Oregon. To plan your American trip of a lifetime go to Visit USA.