Cute naked guys are everywhere, a girl serves pastel-colored cupcakes, and young, smiling hipsters—a fifty-fifty split of scruffy to clean-shaven, I’d estimate—happily take them while shimmying to ’80s hits.

This is the retro-tinged Pony, one of Seattle’s most exuberant gay spots. Mind you, those naked lads are actually blown-up images and pages culled from vintage porn magazines, covering most of the walls. A piñata dangles from above. A brass horse rests on the bar. I’m not sure what the deal is with the cupcakes, and before I can investigate—or get one, wahhh—the music stops and lights snap on, signaling the end of my bar crawl in the way-gay Capitol Hill neighborhood (the large Starbucks here is dubbed “Gaybucks”).

This is the midpoint of my journey up the Pacific Northwest, from Portland to Seattle (with a quick border jump up to Vancouver). These are all pro-gay, progressive, foodie- and bicycle-friendly cities that embrace a “think local” ethos, although eccentric Portland takes the handcrafted and microbatch mind-set to OCD levels, even when it comes to being a drunk (see sidebar pg. 36).

PORTLAND
MERE hours after arriving in Portland, encountering several OTT tattoo-covered hipsters (there’s so much facial hair going on here) and eccentrics, I commented to my friend and fellow travel writer, Andrew Collins, that “this place is just like Portlandia.” The IFC comedy series is to Portland what Sex and the City is to Manhattan, with hysterically spot-on, albeit heightened, takes of its farm-to-table obsession (one butcher shop can tell you everything about the locally raised chickens it sells, including their daily diet and habits), DIY goods that are the rule and not exception (yep, there is actually a shop where they “put a bird on it”) and vehicular etiquette so absurdly polite that while waiting to cross a street, a car stopped and honked at me because they insisted I go first.

I arrived at night, starving. Andrew, who recently launched the quarterly guide to Portland-Seattle-Vancouver, OutCity (outcity.com), picked me up at the airport. Happily, many Portland restaurants offer a late-night, cut-rate “happy hour” food menu, including several near downtown’s Crystal Hotel. Home to a gay bathhouse and bars during raunchier decades past, this landmark has been transformed into a boutique hotel themed after bands and artists that played the nearby live venue, Crystal Ballroom, while a heated basement soaking pool—free to guests—retains a smidge of bathhouse realness. A few gay bars, including the unpretentious and fun Boxxes and Red Cap Garage, are just a block down the street.

Located in the artsy Central Eastside district, the Jupiter, a retro motor lodge turned sassy 81-room boutique, plays host to a number of annual LGBT events, including Latino Gay Pride and furry BearTown, and offers a “Keep Portland Queer” package for gay guests. The adjacent Doug Fir Lounge is a solid dining-and-drinks choice, with late night menus and concerts by local and international indie names to boot.

On my first morning, coffee is a priority, but my head nearly explodes when presented with the wealth of non-Starbucks choices and locals’ divergent opinions on the best place to get it. Portland’s own Stumptown Coffee Roasters has started to kick Starbucks’ ass—their cold-brew iced coffee is pretty awesome—yet there are plenty of smaller, indie, über-craft java joints. Barista receives high marks, while I ended up trying (and enjoying) the everything-to-order, detail-intensive Courier Coffee. Outstanding.

Alas, brunch at Stumptown’s latest spin-off, Woodsman Tavern, next door to Stumptown’s original Division Street location and near the Berkeley-esque Hawthorne neighborhood, proved ho-hum in both overly simple organic food and liberal yuppified atmosphere. Conversely, Tasty N Sons rocks and buzzes thanks to a creative daily brunch menu (e.g. Moroccan chicken hash with harissa cream and over-easy egg or chocolate potato doughnut with crème anglaise). Expect a wait unless you get there godforsakenly early.

I spent a ridiculous amount of time eating and drinking, including  lunch from Portland’s multitudinous food trucks and carts. One truck cluster, known as a pod, is dubbed Cartopia and is located at SE 12th and Hawthorne. Open late and featured in a Portlandia episode, it’s lusted after for Potato Champion’s decadent poutine (french fries with cheese curds and gravy) and Pyro Pizza’s wood-fired pizza (yes, a motherfuckin’ fire oven in a food truck).

Speaking of, I loved the wood-fired pizzas—with toppings like octopus, pork belly and mascarpone cheese and honey—at the new Oven & Shaker restaurant from 2012 James Beard Foundation award nominee Chef Cathy Whims. The “Shaker” part is bartender Ryan Magarian’s original and vintage concoctions like the Pepper Smash #2 (mint leaves, Krogstad aquavit, lime juice, maple syrup and yellow pepper juice).

Come late evening, it’s off to Eagle Portland, which has grown quite popular of late, even with non-bears and in-the-know scene queens. Established in 1967, Darcelle XV Showplace is an enduring drag cabaret with personalities like Poison Waters and Monica Boulevard. CC Slaughters is a busy mainstream gay dance club and bar—you probably have one just like it in your city. And one simply must ogle nude trade, ahem, dancers at Portland’s infamous all-male go-go institution, Silverado. Alas, my timing was off and I missed the zany alternative monthly Blow Pony party. Next time, Portland!

From Union Station, with a hangover, of course, I hopped Amtrak’s Cascades train for a comfortable and complimentary-Wi-Fi-enabled ride up
to Seattle.

Read more about the Pacific Northwest in the new October issue of Instinct, out now!