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.
2138 SE Division St., 503-517-0808, baravignon.com. 5-6 pm Monday-Friday.
[SHELLS AND GRAPES] Wine bar and chicken expert Bar Avignon can get lost in the nouveau-Division sprawl—a shame, because it's home to beautiful house rabbit sausage and an estimable selection of wines on tap. The latter becomes very important at happy hour, when a selected white, red and rosé drop to $7 for a still-fancy pour, next to a $4 charcuterie of the day and $4 cheese of the day, not to mention a $2 oyster of the day and a buck off the cask beer of the day. It's like they're going out of their way to let you know that everything is always very carefully selected. Trust them. MATTHEW KORFHAGE.
Best deal: Anything shelled: $2 oysters, and $9 white-wine mussels that amount to half off. Also, the $7 gin-Campari-grapefruit cocktail is like a greyhound on steroids.
309 SW Broadway, 503-228-2000, coasthotels.com/hotels/oregon/portland/the-benson-hotel. 4-6 pm and 9 pm-close daily.
[A+ PEOPLE WATCHING] Ten minutes into happy hour and the beer taps aren't working at the Palm Court, the Benson's opulent lobby restaurant. The flustered bow tie- and tuxedo vest-clad bartender addresses the bar, whose occupants consist of several pairs of tourists and an inexplicably angry man in a golf shirt: "Anyone have any ideas?" Two biochemists in matching haircuts and polo shirts nervously sip from their glasses of chardonnay. "Maybe it's out of gas?" No one has any ideas. By the time a manager comes to flip on a hidden switch under the bar ("Who knew!" chuckles the bartender), everyone has loosened up and is joining in contagious conversation the way people seem to only when in a new and unfamiliar city. No one orders the food, but the $4 grilled Tillamook cheese sandwich with tomatoes is tempting. KAT MERCK.
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.
1001 SE Water Ave., 503-235-2294, clarklewispdx.com. 4:30-6:30 pm Monday-Saturday.
[DAIQUIRI SPOT] Sitting at Clarklewis' Water Avenue-facing stone-slab counter before the dinner rush, you truly feel like the only person in the room—the best person to be at a nice restaurant. This privacy is welcome while you contemplate the 12-item happy-hour menu, which offers dishes ranging from $1 nuts to a $6 halloumi cheese plate to $7 grilled venison ribs. Beer is still expensive at $6.50—but wine is $6, and so is a hand-shaken daiquiri. SOPHIA JUNE.
Best deal: Consider this: A pepper-bacon cheeseburger at Burgerville is $6.29. Clarklewis' happy-hour, maple-wood-grilled hamburger is $7—down from $13—and this is for a slightly charred, fatty burger served on a wheat bun with greens, pickled red onion and mustard aioli. Pay an extra buck for blue cheese, and eat like you mean it.
404 SE 6th Ave., 503-719-7000, coopershall.com. 4-6 pm Monday-Saturday.
[$7 WINE BOTTLES] When Coopers Hall opened as an airplane hangar for wine—a winery and cidery and barrelhouse and home to more wines on tap than maybe anywhere in the country—it was in danger of feeling cold, impersonal. But it doesn't. There's schmaltz on that bread (both figuratively and literally—you should order it), and a warm bar staff that cares about what it serves. Food costs even at happy hour ($11 burger, $4 olive plate), but there's a $5 house wine for every palate—red, white, rosé or sparkler, plus $2 Rainier for dad and $4 crafts. But the real deal? Check out those bottle discounts on wine to go. MATTHEW KORFHAGE.
Best deal: At happy hour, there are refillable to-go bottles of locally made table wine you can buy for $7. It's like you're in Italy or some shit.
Mama Mia Trattoria
439 SW 2nd Ave., 503-295-6464, mamamiatrattoria.com. 4-7 pm Monday-Saturday, 4-9 pm Sunday.
[ALL COMFORT] Mama Mia is the kind of restaurant you only ever think about when you need somewhere to take your grandmother to dinner. With its decor of faux elegance—rows of chandeliers, gilded mirrors—and menu of the most basic Italian standards, it's the definition of a "safe bet," guaranteed neither to challenge nor offend. The downtown trattoria is hiding one of Southwest Portland's standout happy hours, at least in terms of deals. Available in the corner lounge, the menu more than halves its regular dinner prices while keeping the portions hearty. Everything is in the $3-to-$8 range, including the daily lasagna and manicotti, both of which come drowned in herby tomato sauce. Save room for the zeppole ($4.95 for six), balls of soft, fried dough dusted with powdered sugar, served with sides of jam and Nutella and delivered in an steel basket. Nana will assuredly think it's adorable. MATTHEW SINGER.
Best deal: A 7-inch personal pizza for $7.95.
Mother's Bistro & Bar
212 SW Stark St., 503-464-1122, mothersbistro.com. 3-7 pm Tuesday-Friday.
[DREAM-HOME COOKING] While Mother's Bistro aspires to an airy ladies-who-lunch elegance, its lushly brocaded Velvet Lounge caters to a convivial blend of apres-office tipplers by blending the aesthetic of madame's boudoir with an enlightened take on Mom's Diner fixins. Alongside the purchase of any beverage—say, a house-infused $6 cocktail like the spicily tart jalapeño-cilantro-steeped Dirty Rita or sweetly refreshing Lavender Silk (lavender-infused vodka, lemon juice, honey, Champagne float)—celeb chef Lisa Schroeder's $3.95 happy-hour menu ladles out an array of fun-sized, locally sourced, artisanal comfort staples. The hyper-creamed deviled eggs are sinfully indulgent, chopped liver and crackers offer a more-flavorful trad alternative to pâté, and perfectly crisped fried ravioli arrive bursting with cheese. JAY HORTON.
Best deal: The pairing of $3.95 pigs-in-a-blanket (bite-sized Hebrew Nationals swaddled in puff pastry) with a $6 craft-alcopop-nudging Mom's Lemon Drop allows an after-school snack just like nobody's mother has ever made.
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.
1401 SE Morrison St., 503-234-2427, nostrana.com. 9 pm-close nightly.
The late-night happy hour at O.C.-vibed Nostrana is perhaps Portland's most perfect locale for socially ambitious cheapskates, with the famous pizzas only $7 if you're cool with unadorned margheritas and marinaras, the pasta al forno an equally cheap $7, and a mini-charcuterie plate for $5. The gin comes with housemade tonic for $5 as well—no irritating $2.50 upcharge for Fever Tree as at many houses of fancy tonic—and house wines are the same $5. If you don't let your date see the menu, he'll think you're fancy. If you do, she'll think you're shrewd. Either way, you win. MATTHEW KORFHAGE.
Best deal: The house red and a margherita pizza make a great $12 meal deal.
2225 E Burnside St., 971-271-7166, pixpatisserie.com. 4-6 pm Monday-Friday, 2-4 pm Saturday-Sunday,, midnight-close nightly.
[FREENESS IS SWEET] Pix does everything its own peculiar way—so why should happy hour be different? This dim, red-walled haunt for sherry and Champagne and exotic macarons doesn't offer food discounts, exactly. It just flat out gives away food. As in many bars in Spain, each drink at Pix after midnight or during its first two hours each day will net you a little tapa treat: a bacon-wrapped date, say or a quail egg equally pork-wrapped. Maybe it's an anchovy-stuffed Gilda pepper, who knows? All will go just fine with sangria-like tinto wine, or Baque txakoli—both just $4 at happy hour. And if you go nuts and splurge for a bottle after midnight? That's 10 percent off. But maybe reserve that for Thursday, when happy hour lasts forever.
Best deal: A $4 glass of Txakoli with a free montadito on the side.
Southeast Wine Collective
2425 SE 35th Place, 503-208-2061, sewinecollective.com. 4-6 pm Monday and Wednesday-Friday, 1-3 pm Saturday-Sunday.
[URBAN GRAPES] Is it possible for the city's best-loved wine bar to be underrated? Not only has Tom Monroe and Kate Norris' wine collective been an incubator for some of the best wines in town—including, especially, the co-founders' own Division Winemaking—but the bar itself is a worthy showcase. And at happy hour, not only do you get $2 off a glass of wine, but also off the already-generous flights. You can get an all-too-familiar pinot noir flight ($13), but don't. Go for the "surprise" flight—equally likely to tap a lovely Basque Txakolina as a first-vintage chardonnay from natural-wine up-and-comer Statera, or a truly singular syrah from Norris' own Gamine imprint. Althea Grey Potter's fine small-plates menu drops a buck at happy hour as well. MATTHEW KORFHAGE.
Best deal: The $10 tap-wine flight drops to $8 for three half-glasses. How nice.
5425 E Burnside St, 503-236-3610, tannerybarpdx.com. 4-6 pm and 10 pm-close daily.
[MOUNT RAINIER] A tricked-out mountain cabin filled with bourgeois mixology and meaty comforts at the edge of Tabor, the Tannery also doubles as the 'hood's best neighborhood bar. And being neighborly, as a bar, often means being cheap enough to pop into on the daily. And so happy hour involves $1 Rainier bottles and Tecate cans, plus wine for $5—a solid date for the erstwhile Mikes and Mollys of the world, when matched up with three-deep sliders at $4 apiece. MATTHEW KORFHAGE.
Best deal: A buck for Rainier keeps Jack from becoming a dull boy.