The Headliners Club in Lake Oswego pairs pro production with a full restaurant and bar, so your night out sounds great and tastes better.…
17880 SW McEwan Rd
“The Headliners Club in Lake Oswego pairs pro production with a full restaurant and bar, so your night out sounds great and tastes better. Weekly karaoke, Mad Poker, and cornhole keep it buzzing, and the events calendar stays stacked with shows, games, and unlimited good vibes.”
From the Lake Oswego newsletter, September 15, 2026
McMenamins John Barleycorns pours their own ales and spirits and turns out Northwest-style pub fare built around fresh, seasonal…
14610 SW Sequoia Pkwy (Tigard)
“McMenamins John Barleycorns pours their own ales and spirits and turns out Northwest-style pub fare built around fresh, seasonal ingredients. It’s the kind of comfy, high-ceilinged spot where a burger, a pizza, or a bowl of soup alongside a house pint fixes most days.”
From the Lake Oswego newsletter, September 9, 2026
For an easy weeknight hang close to home, FlyBoy Brewery & Pub keeps a rotating tap list of their own beers alongside regional picks, plus…
15230 SW Sequoia Pkwy (Tigard)
“For an easy weeknight hang close to home, FlyBoy Brewery & Pub keeps a rotating tap list of their own beers alongside regional picks, plus stone-fired pizzas, burgers, sandwiches, and salads.”
From the Lake Oswego newsletter, September 10, 2026
Peppers is that reliable, low-key spot when you want a pint, pubby comfort food, and actual conversation before the band kicks up on…
17777 Pilkington Rd
“Peppers is that reliable, low-key spot when you want a pint, pubby comfort food, and actual conversation before the band kicks up on weekends. Weekly events, bingo and pool tourneys keep it lively, and yes, you can play Oregon Lottery while you wait on your order.”
From the Oregon City newsletter, September 11, 2026
Need a low-key hangout this week, Gresham? The LINQ by Mr. Hookah - Portland pairs richly packed hookah bowls with bold, exotic flavor…
18345 SE Stark St (Portland)
“Need a low-key hangout this week, Gresham? The LINQ by Mr. Hookah - Portland pairs richly packed hookah bowls with bold, exotic flavor combos and genuinely attentive service rooted in Middle Eastern hospitality.”
Scotch Lodge is a cocktail bar for Whisky lovers curated by Tommy Klus, with a playfully modern Pacific Northwest inspired menu from Chef…
215 SE 9th Ave #102 (Portland)
“Scotch Lodge is a cocktail bar for Whisky lovers curated by Tommy Klus, with a playfully modern Pacific Northwest inspired menu from Chef Tim Artale. Expect rare and unique bottles, whisky-forward cocktails, and a vintage-leaning vibe that makes weeknights feel special... even if you’re just celebrating Tuesday.”
Secret Grove is an artist-built cocktail lounge and music venue, with every detail from stage to seating tuned for listening, dancing, and…
1425A NW Flanders St (Portland)
“Secret Grove is an artist-built cocktail lounge and music venue, with every detail from stage to seating tuned for listening, dancing, and connecting.”
Breakside Brewery & Tasting Room keeps Lake Oswego stocked with rotating, award-winning beers from an employee-owned crew that nails West…
5821 SE International Way (Milwaukie)
“Breakside Brewery & Tasting Room keeps Lake Oswego stocked with rotating, award-winning beers from an employee-owned crew that nails West Coast IPA, Summertime Lager, Breakside White, and even an Oktoberfest. Slide in this week for something new, maybe a barrel-aged release, definitely crushable.”
Freshly baked bread meets great bottles at The Fates Bread and Bottle Co., a one-kitchen-witch wine shoppe and veg-forward eatery serving…
6664 SE Milwaukie Ave (Portland)
“, a one-kitchen-witch wine shoppe and veg-forward eatery serving thoughtful, seasonal bar bites and easy-to-love pours plus cocktails. Run by vegetarian chef Chanelle, it's a warm, linger-a-while spot with occasional supper clubs and other community events worth building your week around.”
Boundary Social Club is a members-only wine retreat where talented staff pour exceptional wines and top-shelf spirits in a relaxed, refined…
126 SW Mitchell St (Portland)
“Boundary Social Club is a members-only wine retreat where talented staff pour exceptional wines and top-shelf spirits in a relaxed, refined space, with a wine vault, personal bottle storage, and members-only tastings and cocktail classes... basically your new spot to entertain friends or clients without the scene.”
Freeman BarrelHouse is a woman-owned, whiskey-focused bar where you can linger over pours and flights, try classic or craft cocktails, and…
4630 SE International Way #200 (Milwaukie)
“Freeman BarrelHouse is a woman-owned, whiskey-focused bar where you can linger over pours and flights, try classic or craft cocktails, and even grab an espresso when you need a second wind. The cozy, vintage-lit room pairs nicely with charcuterie, Thai, or sushi...”
McMenamins Raleigh Hills Pub is that comfy neighborhood spot with a double pyramid roof, vaulted wood ceilings, and a trompe-l'œil mural…
4495 SW Scholls Ferry Rd (Portland)
“McMenamins Raleigh Hills Pub is that comfy neighborhood spot with a double pyramid roof, vaulted wood ceilings, and a trompe-l'œil mural featuring longtime regulars. Swing by for Northwest-style pub fare made with seasonal, local ingredients and the easygoing pint you were probably craving anyway.”
Whether you’re in a bold-red mood or craving something crisp, No Doubts Wine Bar keeps it fun with a rotating lineup and the kind of…
8408 N Lombard St (Portland)
“Whether you’re in a bold-red mood or craving something crisp, No Doubts Wine Bar keeps it fun with a rotating lineup and the kind of elevated comfort food you actually want with a glass. Slide in this week for chill vibes, zero pretense, and just enough surprise to upgrade a weeknight.”
Hop N Cork keeps things lively with a rotation of sought‑after craft pours, an Oregon‑first tap list, and a legit growler game, plus a…
17450 Lower Boones Ferry Rd
“Hop N Cork keeps things lively with a rotation of sought‑after craft pours, an Oregon‑first tap list, and a legit growler game, plus a scratch menu built on local ingredients. This week, meet a friend, sample something new, catch the game.”
From the Lake Oswego newsletter, September 22, 2026
Trade the gray for a glimmering pearl at Hale Pele, where over 50 classic and contemporary tiki cocktails use fresh juices, premium…
2733 NE Broadway (Portland)
“Trade the gray for a glimmering pearl at Hale Pele, where over 50 classic and contemporary tiki cocktails use fresh juices, premium spirits, and house-made syrups. Pair them with island-inspired small plates, listen for thunder and volcanic eruptions, and pretend your inbox drifted out to sea.”
Schilling Cider House & Gluten Free Kitchen keeps 33 rotating draft ciders flowing, with curated flights if you like to taste around, plus…
2800 SE Division St (Portland)
“Schilling Cider House & Gluten Free Kitchen keeps 33 rotating draft ciders flowing, with curated flights if you like to taste around, plus a fully gluten-free menu where the fan-favorite corndogs steal the show. Not into cider? Swing by this week, they pour craft beer, gluten-free beer, cocktails, and solid NA picks.”
Monte Ferro Winery connects the best vineyards with the finest winemakers to turn great fruit into bottles that nail quality and value.…
2240 Prestwick Rd
“Monte Ferro Winery connects the best vineyards with the finest winemakers to turn great fruit into bottles that nail quality and value. Upgrade Tuesday dinner, grab a couple, and let their careful, detail-obsessed style bring real joy to your table.”
Portland Wine Bar & Winery Tasting Room keeps the weeknight vibe strong with small-batch Oregon and Washington pours from the coast-born…
526 SW Yamhill St (Portland)
“Portland Wine Bar & Winery Tasting Room keeps the weeknight vibe strong with small-batch Oregon and Washington pours from the coast-born winery in Manzanita.”
The Rambler is a cozy converted-bungalow bar in Portland’s Mississippi Avenue District serving cocktails, local craft beer, and a great…
4205 N Mississippi Ave (Portland)
“The Rambler is a cozy converted-bungalow bar in Portland’s Mississippi Avenue District serving cocktails, local craft beer, and a great food menu. Perfect for low-key get-togethers or a casual celebration, with trivia nights and a friendly vibe that makes it feel like your home away from home.”
Cougar Crest Estate Winery brings estate-grown Walla Walla character to your week, from savory, gamey Rocks District Syrah to bright…
310 N State St #108
“Cougar Crest Estate Winery brings estate-grown Walla Walla character to your week, from savory, gamey Rocks District Syrah to bright Viognier and Albariño, plus classic Cabernet and Merlot, all from their own vineyards and an award-winning program started in 2001. Perfect for a backyard hang or dinner upgrade.”
Craving reliable, really good pizza that doesn’t require leaving the couch? Bellagios Pizza Pub does specialty pies, build-your-own…
1399 McVey Ave
“Craving reliable, really good pizza that doesn’t require leaving the couch? Bellagios Pizza Pub does specialty pies, build-your-own masterpieces, and legit toasted grinders, all on fresh dough that tastes like someone actually cares. Treat yourself this week, they’ll run it to your door or keep it ready for pickup.”
Keep it simple and tasty this week at Coasters Brew Pub, a cozy spot built on community, creative comfort food, and cold pours. Expect a…
18650 SE McLoughlin Blvd (Milwaukie)
“Keep it simple and tasty this week at Coasters Brew Pub, a cozy spot built on community, creative comfort food, and cold pours. Expect a thoughtful tap list with 16 beers, cocktails that play nice with comfort-food plates and brunchy bites, plus trivia-worthy vibes when you want low-key fun.”
If your idea of perfect Portland is a glass of great wine with bread and cheese in a wood-paneled room full of vintage character, The Old…
1433 NW Quimby St (Portland)
“If your idea of perfect Portland is a glass of great wine with bread and cheese in a wood-paneled room full of vintage character, The Old Portland Wine Bar nails it. It’s intimate, unfussy, and exactly the low-key neighborhood retreat you’ll want in your weekly rotation.”
Sports, rotating specials, and fresh-ingredient plates make Berkeley's Bar & Grill an easy weeknight win for Tigard locals. Grab a…
6302 Meadows Rd
“Sports, rotating specials, and fresh-ingredient plates make Berkeley's Bar & Grill an easy weeknight win for Tigard locals. Grab a cocktail, share some bar bites, and add your pup’s pic to their dog wall that sends love to Oregon Dog Rescue while you catch the game with friends.”
Tabor Tavern is that rare Portland spot that nails cozy gastropub fare alongside legit brunch and happy hour. Grab a jar of their salty,…
5325 E Burnside St (Portland)
“Tabor Tavern is that rare Portland spot that nails cozy gastropub fare alongside legit brunch and happy hour. Grab a jar of their salty, savory, sweet bacon jam to-go, then settle in with good drinks and the kind of neighborhood energy you wish every week had.”
Craving a little Sunday spice? Tavern on Kruse keeps it local and seasonal, pairs it with a handpicked wine list, and tonight they’re…
4835 Meadows Rd #133
“Craving a little Sunday spice? Tavern on Kruse keeps it local and seasonal, pairs it with a handpicked wine list, and tonight they’re hosting live band karaoke so you can belt it out between bites. A perfect excuse to gather your Tigard crew and call it dinner plus a show.”
Aji Tram brings farm fresh, Asian-rooted dishes with a playful Pacific Northwest twist, plus a proper bar program for when you want…
4477 Lakeview Blvd
“Aji Tram brings farm fresh, Asian-rooted dishes with a playful Pacific Northwest twist, plus a proper bar program for when you want something sippable with real personality.”
Feeling like a midweek upgrade? Friendship Vietnamese Kitchen x Stem Wine Bar pairs soulful Vietnamese dishes and cocktails with a fun…
3920 N Mississippi Ave (Portland)
“Feeling like a midweek upgrade? Friendship Vietnamese Kitchen x Stem Wine Bar pairs soulful Vietnamese dishes and cocktails with a fun lineup of natural French and Oregon wines, including flights and plenty by the glass.”
45th Parallel Wines is where global finds meet chill neighborhood energy. Est. 2017, this bar-meets-bottle shop rotates wine, beer, cider,…
8527 N Lombard St (Portland)
“45th Parallel Wines is where global finds meet chill neighborhood energy. Est. 2017, this bar-meets-bottle shop rotates wine, beer, cider, sake and spirits, with deli bites from vegetarian terrine to house made sausages, plus regular events that keep the community buzzing.”
Nonprofit improv and sketch home base Curious Comedy Theater keeps the jokes sharp and the vibes welcoming, spotlighting underserved voices…
5225 NE Martin Luther King Jr Blvd (Portland)
“Nonprofit improv and sketch home base Curious Comedy Theater keeps the jokes sharp and the vibes welcoming, spotlighting underserved voices with a full bar, the raucous Curious Comedy Showdown, and classes from improv to stand-up to musical improv. Rent a stage for your crew or level up your own funny.”
Gubanc's Restaurant has been serving Lake Oswego since 1976 with from-scratch pub fare made from local, organic ingredients and a solid…
16008 Boones Ferry Rd
“Gubanc's Restaurant has been serving Lake Oswego since 1976 with from-scratch pub fare made from local, organic ingredients and a solid draft lineup. It’s family-run across three generations, freshly remodeled, and reliably cozy when you just want good food without the fuss.”
From the Oregon City newsletter, September 2, 2026
Whether you’re Portland-bound for errands or a show, Cat's Paw Saloon is a low-key spot for cocktails and cold beer, with a dog-friendly…
3565 SE Division St (Portland)
“Whether you’re Portland-bound for errands or a show, Cat's Paw Saloon is a low-key spot for cocktails and cold beer, with a dog-friendly patio that makes lingering feel easy. A solid backup plan when the home bar feels tired and the dog needs fresh air.”
Down an alley in NW Portland, Bar Diane nails the balance of wines from independent producers, classic martinis and spritzes, and a…
Entrance on NW 21st Ave through the gate next to Eb & Bean (Portland)
“Down an alley in NW Portland, Bar Diane nails the balance of wines from independent producers, classic martinis and spritzes, and a globally minded, ingredient-driven menu that slides from snacks to dinner. It’s the neighborhood spot where “just one glass” turns into great conversation and an unhurried evening.”
Whether you come for the mystery or just a solid night out, Hawthorne Hideaway nails the Twin Peaks mood without taking itself too…
2221 SE Hawthorne Blvd (Portland)
“Whether you come for the mystery or just a solid night out, Hawthorne Hideaway nails the Twin Peaks mood without taking itself too seriously. Mellow booths up front, pool tables in back, and a thoughtful cocktail menu make it an easy go-to when you want cozy weirdness done right.”
