529 NW 23rd Ave., 503-445-7400, 23hoyt.com. 4-6:30 pm daily, 9-11 pm Friday-Saturday.
[CHEAP DATE] Longtime restaurateur Bruce Carey's Northwest Hoyt Street staple has seen many iterations over its 10 years of existence, but the current one—indoor trees, potted succulents, the words "gastropub" and "tavern" recently affixed to menus and signage—seems to have struck a chord with the influx of transplants and millennials looking for the Portland they saw on TV. They're here fashionably ignoring each other while Instagramming one of the markedly average $6–to-$8 happy-hour cocktails (the "dealer's choice" is a safe bet). Nab a seat at the circus and order the popular $3 charcuterie plate, which, when paired with four deviled eggs topped with bacon crumbles and a dusting of Parmesan ($2), actually makes an excellent light supper for under five bucks. KAT MERCK.
Best deal: The $3 "daily charcuterie" presents a generous pile of meat alongside a full complement of sliced baguette, pickled vegetables and mustard.
2108 NW Glisan St., 503-224-7919, bartinipdx.com. 4-6:30 pm, 9:30 pm-close daily; all day Sunday & Monday. Weekend evening Happy Hour does not include cocktails.
[CHEESE PLZ] There are a few places you'll go that will cause certain people to call you "basic." Buffalo Wild Wings, all of Southwest Portland—and Bartini. It's like Portland's own little Sex and the City bus tour shrunk down into a tiny room bordering a fondue restaurant. But with shiny black walls, giant paintings of goldfish in martini glasses, princessy glass chandeliers, a dozen-page book of 100-plus drinks, and an '80s Jazzercise-esque logo, what's not to love? It'll take a while to eat your way through the 30-item food menu (each with its own happy-hour price), so here's a tip: The Gorgonzola-brie fondue is the best, and it's easily shareable. Skip the $6 cheeseburger, but definitely get the $3 mashed potatoes in a martini glass, served with a wedge of brie. Drinks are half-price during happy hour, which is most of the hours Bartini is open. Expect sweetness and possibly a flower or sprig of mint; but at $4 apiece, these drinks seem to say what your best friend would. Treat yourself, girl—you deserve it! SOPHIA JUNE.
Best deal: $4 cocktails. If you're not into sweet, go for the lemon-basil. The $8 fondue pot comes with a plate of sourdough bread cubes.
210 NW 11th Ave., 503-296-4906, deschutesbrewery.com. 4-6 pm daily.
[HOMETOWN TOURISTING] With all the great new breweries in Oregon, it's easy to forget how good Deschutes' beers remain. Even at the chichi Pearl location, Deschutes is brewing a wide variety of great beers a couple of blocks from Powell's. But it costs a lot for non-tourists—burgers and $6 pints are expensive. Enter happy hour, when rotating pints cost $3.50. Drink those. MATTHEW KORFHAGE.
Best deal: $3.50 pints.
Fat Head's Brewery
131 NW 13th Ave., 503-820-7721, fatheadsportland.com. 3-6 pm and 9 pm-close Sunday-Thursday. (Damn you, pointlessly expensive Friday!)
[WING THING] Fat Head's massive Pearl District brewhouse may look like an outlet-mall version of T.G.I. Friday's, but the beer is some of the best in Portland, and there are everything-must-go, Trader Joe's-style happy-hour deals: seven $5 wines, $6.50 margs and bloodies that will twist your sister, $7 pizzas, $6 wings and a $5 giant pretzel or plate of chicken fingers. All the better to down that dollar-off pint of Semper FiPA, voted best IPA in Portland in a blind tasting. MATTHEW KORFHAGE.
Best deal: $6 wings and a cheap, very good beer will do.
801 NW 23rd Ave., 503-477-9505, pdxfireside.com. 3-5:30 pm Monday-Friday.
[BOOZE, UP] Fireside offers one of the finest early-afternoon drunks in town. It's shocking there aren't more retired Nob Hill doctors ruining their dinners here every day at 4 pm. The bites, from $6 flatbread to a $7 French dip that's worth precisely $7, offer neither full meals nor especially exciting deals. But dear Lord, that $6 cocktail menu is all booze—and all good booze. In particular, the excellent Preakness—bourbon, vermouth, Benedictine—will get you well down the track, as will the inventive Hoopla mixing brandy, Cocchi vermouth and triple sec, and a gin-vodka Vesper martini, designed by James Bond himself, that will make you think fondly of Eva Green. MATTHEW KORFHAGE.
Best deal: The $6 Preakness is a winner.
232 NW 12th Ave., 503-241-4009, hamletpdx.com. 4-7 pm Monday-Saturday.
[CURED HAM, CURED PEOPLE] At Ryan Magarian and Cathy Whims' ham-centric Pearl District bar, prices can skyrocket—except at happy hour. La Quercia prosciutto is the pride of Iowa, a beautifully marbled, cured ham that's just $5 for a thinly sliced ounce during happy hour alongside other La Quercia cuts. A select draft knocks down to $4 and Portuguese wine is $6, but drink liquor. Hamlet's well-made happy-hour cocktails drop to $7 and $8 (from closer to $12). The menu rotates, but standout regulars are the Blood and Sand and Sazerac, two often middlingly prepared cocktails that benefit from Magarian's meticulous, almost fussy liquor sourcing and sizing—seriously, the man mixes Peychaud's and Angostura bitters 3-to-1 for his preferred Sazerac-bitter blend (an eccentricity also preferred by Clyde Common's Jeffrey Morgenthaler)—and he dug deep for the Famous Grouse blended scotch for the Blood and Sand. It matters. MATTHEW KORFHAGE.
Best deal: $9 gets you smoked ham and mezcal together, as they should be. But for belly-filler, get a $6 tortilla espanola with your $7 Blood and Sand.
Irving Street Kitchen
701 NW 13th Ave., 343-9440, irvingstreetkitchen.com. 4:30-6 pm daily.
[FRIED OYSTERS] Irving Street Kitchen's Southern-influenced cuisine isn't cheap during dinner, so take advantage of happy hour when you can. Drinks—selected wine, a couple cocktails, and PBR with a whiskey back—are just $6 each, and some of the food offerings are smaller yet well-executed dishes off the regular menu. Peppercorn-sauced meatballs ($7) make for a hearty snack, or go a lighter route with chicken-fried oysters ($6), which come with tasty Herbsaint aioli. ROB FERNAS.
Best deal: $7 meatballs, $6 wine.
417 NW 21st Ave., 503-228-6614, facebook.com/mbar.portland. 6-8 pm daily.
[CHEAPEST GOOD WINE] This glamorous matte-red broom cupboard of a wine bar is tiny, sultry and unparalleled as an intimate date spot on 21st Avenue. But it's not for firsts. Even whispers boom in the one-room, candle-lit bar, where the bartender makes friends with everyone, from 40-something neighbors sipping pinot noir to bar backs seeking refuge from 21st's bro bars. It is, however, a perhaps unparalleled date spot for another reason. The happy hour runs till 8 pm—late enough you won't seem cheap for suggesting 7 pm as a meeting time—and in addition to $4 well-chosen draft beers, you get $3 off glass pours of wine, leading to outright ridiculous deals on the lower-priced pours. Take credit for splurging on three rounds of a well-rounded red that actually only costs $4. Baller on the cheap. ENID SPITZ.
Best deal: It's possible to get a decent, well-selected glass of wine for $3 at happy hour. That can be said of…nowhere else.
Mi Mero Mole
32 NW 5th Ave., 971-266-8575; mmmtacospdx.com. 2-6 pm Monday-Saturday.
[MARGARITA AND MOLE] First, the disclosure: Triple-M boss man Nick Zukin is a sometime contributor to WW, and someone we reach out to for intel on other spots in this guide. Zuke's own place is dedicated to his passion for Mexican street food, particularly the stewy taco fillings known as guisados. But he obviously also has a soft spot for the day drinker—because the Chinatown location offers day deals that best almost any in the entire city, not only $2.50 beers and $4 margaritas (!), but nachos that drop to $5 and three-deep huitlacoche flautas for a mere $4. That's not even counting the daily deals like all-you-can-eat taco Tuesdays for $14.75, or the all-day, everyday deal of a burrito, beer and shot for $10.
Best deal: Seriously, a $4 margarita with $5 nachos is gringo paradise. MATTHEW KORFHAGE.
1632 NW Thurman St., 503-894-8136, olympiaprovisions.com. 3-5 pm daily.
[THE BEST WURST] OP doesn't call its happy hour a happy hour. It is, instead, a "midday menu" filling in that awkward two hours between times anyone would sensibly lunch or dine. But it is here you'll fine the sweet spot on pricing, with a miniature charcuterie platter featuring Portland's finest cured meats for $7 (you can get the full $18 house charcuterie board if you like), a $6 cheese plate, and the city's best hot dog for $5—it isn't even close, and comparing it to other hot dogs is like comparing country ham to other ham. Oh, but did you actually want ham? A really nice ham sandwich is $7, and you can eat it outside or right by the entryway butcher counter—thus treating a fine restaurant as your own personal deli counter. Because it also is your deli counter, except with cocktails. MATTHEW KORFHAGE.
Best deal: The $5 dog, dawg.
1020 NW 17th Ave., 503-943-2780, paymasterlounge.com. 2-6 pm daily.
[PATIO POOL PARTY] If you're in Northwest Portland sucking down $1.50 happy-hour Hamm's and downing $5 nachos under an anatomically suspect drawing of a cat's penis—well, you're here, at a bar named after a check-cashing spot that also happens to be home to the best patio in Northwest Portland. Hell, that pool-tabled patio is so good that even a drunkenly driven car tried to park on it once. For four hours each day in this labyrinthine bar—complete with a small front patio to mirror the huge one in back, a weird-balls vending machine and an even weirder TV room—$7 nets not only a burger but the french fries that rightly go with it, and Sauza tequila costs just a dollar more than a $3 well-vodka soda. MATTHEW KORFHAGE.
Best deal: $7 burger and fries, $4 Sauza.
Pope House Bourbon Lounge
2075 NW Glisan St., 503-222-1056, popehouselounge.com. 4-7 pm daily.
[WHISKEY PATIO] Pope House has a generous happy hour—everyday from 4 to 7 pm, $6 gets you a well-made brown derby (an Old Fashioned variant with grapefruit) or jackalope (a Negroni variant with IPA and grapefruit). But among the $6 pours, the only one that will reward not getting the excellent $10 Old Fashioned is the Four Roses-vermouth-bitters half man (of which the other half is obviously a Manhattan). If you're truly going budget, pick up a $4 pour of Rebel Yell or Evan Williams and drink it with a $7 pair of bulky pork sliders that will serve as a full meal while you enjoy one of Nob Hill's finest patios. MARTIN CIZMAR.
Best deal: $4 Rebel Yell (mixer optional), $7 pork sliders.
Rae's Lakeview Lounge
1900 NW 27th Ave., 503-719-6494, raesportland.com. 2-6 pm daily.
[DAY DRUNK] Oh, Rae's, you are so strange—a patio with a view of a now-fictional lake, a Montgomery Park after-work rec room, a day-drinker's haven that looks a little like an airport lounge. Everything is cheap, but what is cheap is always unexpected. Rillettes for $4? A croque monsieur for $6? A $7 mini-Bourguignon that is essentially a Frenchified pot pie? They are not high-class despite European pedigree, but they'll hit the spot after celebrating with High Life's Champagne for a mere $1 or a dizzyingly cheap $9 half carafe of wine that's $3 by the glass. Although…the real stomach-filler for the day-drunk is the huge $3 doughy biscuits and gravy. Too late for happy hour? No problem. Rainier pints are $1 after 9 pm. Too early for happy hour? No problem. Mimosas are $1 at brunch. Or you can just get a 61-ounce rum-and-gin "Thunder Bowl" for $24 anytime. Oh, God—you're never leaving. MATTHEW KORFHAGE.
Best deal: $1 High Life, $1 Rainier, $1 mimosa, $3 biscuits.
2112 NW Kearney St., 503-221-1195, serratto.com. 4-6 pm daily.
[BUTTON-DOWN PASKETTI] Serratto is like the Nob Hill neighborhood's idea of a living room during happy hour—upscale on the cheap, though the favorite remains an $9 succulent, medium-rare half-pound burger with every version of fat, salt and sugar: beef, bacon, brioche, barbecue sauce and fried onion. It comes with fries—no happy-hour stinting here, as evidenced also by a generously poured $6 margarita (which can be swapped for a $6 cosmo or lemon drop, if that's you). The $5 house wines are table wines in the European style—unobtrusive, decent—better paired with the $8 spaghetti and meatballs. The latter is not as decadent as the burger, but when that's what you crave, nothing else will do. MATTHEW KORFHAGE.
Best deal: $9 burger, $8 spaghetti.
1015 NW Everett St., 503-445-8109, teardroplounge.com. 4-7 pm Monday-Friday.
[FINEST MIXED DRINKS] The rare Portland bar where you'll feel out of place among the olds and feel underdressed in a hoodie, this Pearl spot definitely isn't a hang. And yet, if you're out for a night in the neighborhood and wearing a shirt with buttons, you should plan to drop by, because Teardrop makes some of the very finest cocktails in the city. And at happy hour, some of them are $7. In particular, the Neverland is a raspberry-vodka sparkler that tastes like a very subtle take on British hard candy, while the Graduate is a stiff Manhattan leavened by curacao. Don't be suckered by the $5 kitchen deals—that "grown-up" grilled cheese is a naive notion of adulthood involving crusty bread, and $5 for olives is no deal I recognize. You're here to drink fine things, and so you shall. MARTIN CIZMAR.
Best deal: The Graduate is a fine, fine $7 cocktail.
226 NW 12th Ave., 503-224-4909, vaultmartinibar.com. 4-7 pm daily; all day Sunday, Monday and for ladies-only Thursday.
[7 DEADLY SINS] Vault is the spot I always imagined I'd frequent as a grown-up: a dimly lit bar with low couches, a marble bar, an exposed-pipe ceiling painted black, groups of high-heeled 30-somethings grabbing bacon-stuffed appetizers after work, and a pink drink in a martini glass in front of me. Thanks to happy hour, when prices are slashed by $3 to $4 for most items, I can achieve this aesthetic. For just $5, you can get bacon-wrapped dates or shrimp sunomono. The drink menu is daunting, but you can't go wrong with the $6 Seven Deadly Sins cocktails. The Envy is a sour without being overly sweet, a mix of citrus vodka, melon liqueur, pineapple juice and fresh lime with pineapple garnish. SOPHIA JUNE.
Best deal: The Seven Deadly Sins cocktails are $6 on Mondays. Fresh popcorn with Parmesan, red pepper, white truffle oil is $4 and easily split between two people.