Pépé Le Moko Minh Tran

CONSIDERING OUR countless microbreweries and happy hours, one could declare Portland America's most alcoholic city. But we possess another claim to drinking fame—a happening basement bar scene that takes the boozing downstairs.

While you could say this has something to do with the city's on-again, off-again relationship with the sun, it's hard to deny the allure of our subterranean drinking spots. Not only does heading below the surface help break up the late-night routine, it adds a certain frisson to the bar experience.

So whether you seek romantic seclusion with pricy drinks or a flannel-themed tunnel party, here's a guide to the best bars in the bowels of the city.

For Film Noir-Inspired Romance: Pépé Le Moko (407 SW 10th)

A coral-colored neon sign illuminates the window at Pépé Le Moko's street-level entrance. Once inside, you'll find what appears to be a pantry of cocktail supplies and a classy hostess who will lead you down a winding flight of stairs to a dimly lit tunnel below the Ace Hotel—evoking the film-noir thriller of the bar's namesake.

You might want to refer to Pépé as a speakeasy, but resist that temptation. You'll find no Prohibition-era drinks on the menu, only candy-like cocktails created by Portland's renowned bartender Jeffrey Morgenthaler. His sweet concoctions don't come cheap, but they certainly don't disappoint. A clear favorite, the minty Grasshopper (priced at a wallet-draining $14) blends crèmes de menthe and cacao with vanilla ice cream—perfect for an intimate escape.

For an Art School Reject's Hideaway: Jack London Bar (529 SW 4th)

After walking past huddles of gray-haired men and a maze of pool tables, an inconspicuous sign points down a flight of stairs to the Jack London Bar—a graffiti-ed basement lounge beneath downtown's Rialto Poolroom. The low-key dive feels illicit, and you'll anticipate an edgier crowd. But instead, the dingy Jack London has become an unexpected refuge for Portland's art school rejects—thanks to hosting offbeat readings and spoken word performances in the recent past.

Jack London's appeal has little to do with its subpar menu—featuring a typical variety of cocktails, a limited beer selection, and drunk-food classics. It comes from the strange sensation of escaping a surface world of big-bellied men and blaring TVs to a grungier hideaway below, one filled with loveable freaks of all colors.

For a Cave-Like Speakeasy: Ringlers Annex (1223 SW Stark)

Bring up McMenamins' chain of microbrew pubs in casual conversation, and you'll receive a mixed reaction from your pickier beer pals. Expect a few raised eyebrows and disparaging sighs, but don't let that discourage you from discovering the pint-sized Ringlers Annex cellar bar, located beneath the quirky Crystal Hotel.

Upon descending a narrow flight of stairs, you'll find a damp speakeasy that seems more like a converted cave than it does a basement. Candle-lit tables crowd the tight space, pushing the ambiance from cozy toward cramped.

The bar shares its menu with the Zeus Café above—meaning Northwest and American-inspired pub fare. The drink menu, on the other hand, features McMenamins brews like the Hammerhead, a classic Northwest-style pale ale. While the Annex may not be a secret, it sure feels like one.

For a Flannel-Themed Tunnel Party: Shanghai Tunnel (211 SW Ankeny)

Portland's subterranean history is filled with mythic tales of Shanghaiin'—trickery and kidnapping in the now-abandoned tunnels beneath Old Town. Modern Portlanders wanting to relive these likely untrue legends head to the Shanghai Tunnel, a bar that's converted a section of the tunnels into a bro-ish dive.

At ground level, the bar may appear dead and a bit sketchy, but wander downstairs and you'll discover a dungeon-like liquor haven lit with paper lanterns. The bar has become a weekend institution on downtown's frat-party circuit, and it's easy to see why. Half a dozen pinball machines line a wall, and flannel-clad guys wearing Blazers caps chat up girls in miniskirts sitting around tables sticky with spilt PBR. Go mid-week to avoid those crowds.

An Asian-themed food menu offers a nice respite from the typical burgers-and-truffle-fries fare found in other nearby estabishments—the panko-crusted tofu with noodles in peanut sauce satisfies drunk hunger quite nicely.

For Getting Lost: Upright Brewing (240 N Broadway, Ste. 2)

Finding this cash-only tasting room can test your patience, but Upright Brewing's celebrated beer is well worth the hassle. It's located beneath the Leftbank Project, a commercial development off NE Broadway. Once inside the complex, you'll want to take the elevator by the Stingray Café rather than losing time searching for the stairway. Downstairs, you'll discover a makeshift taproom that seems like a poorly kept secret—a few crowded picnic tables surrounded by barrels with taps on the wall.

A nice break from the IPA onslaught of other local brewers, Upright's farmhouse-inspired beers build on Belgian and French traditions. With five-ounce tasters priced at a mere $1.50, a flight of everything on tap is guaranteed to be a euphoric experience, verging on spiritual, for beer aficionados of all stripes—certainly a worthwhile pilgrimage.