THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!

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A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!

CANCELED: Bailey Bryan & Leah Kate @ Lola’s Room | Pop, R&B, Country

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September 24 @ Lola’s Room – Following her buzzy debut single, “Own It,” Bailey Bryan quickly became an Artist to Watch (Rolling Stone, Billboard, Entertainment Weekly) while earning praise from the New York Times for her “rich songwriting.”

Win Tickets ($40): Siren Nation & The Old Church Concert Hall Present An Evening with The Billie Holiday Project | Featuring the Bay Area’s Finest Jazz Musicians

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September 17 @ The Old Church Concert Hall – The Billie Holiday Project, led by Stella Heath, celebrates the music of Lady Day!

Kickstand Comedy Presents The Bitchuation Room Podcast LIVE @ Alberta Abbey | Comedy, News & Revolution, Featuring Francesca Fiorentini & Friends

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September 2 @ Alberta Abbey – One part comedy, one part news, and one part scheming for the revolution, The Bitchuation Room is a thoughtful look at leftist politics with a heavy dose of humor.

MANY Portland Weekend Events & Giveaways ($600+): Easterseals Zoo Benefit, Willamette Flea, Live Music, Outdoor Movie Nights & More! | August 26-29, 2021

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The weekend is back, Portland! Summer’s winding down but there’s still plenty of time to find some vintage goodies at this weekend’s Willamette Flea. Bring the whole family and walk/run for a good cause at the Easterseals benefit at the Oregon Zoo! And Pix Patisserie is hosting their final Flamenco Friday of the year!

Portland in the News: Audiences Returning to Area Theaters; More Are Traveling; Tribal Member Nominated to Lead NPS & More | August 26, 2021

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Despite another COVID-19 surge, stages across the city are planning to host events and artists. Many venues will require proof of vaccination or a negative COVID test.

President Biden has nominated Umatilla tribal member Charles F. “Chuck” Sams III to lead National Park Service. If confirmed, Sams would be the first Native American to hold the position.

Win Tickets ($30): The Old Church Concert Hall Presents An Evening with Jackie Venson | Singer/Songwriters, Guitarist, Blues, Soul

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September 14 @ The Old Church Concert Hall – Jackie Venson is a multi-instrumentalist, singer/songwriter known far and wide for her beautifully complex music and blazing guitar skills.

Win Tickets ($46): The Old Church Concert Hall Presents Golden Retriever, Saariselka | Electronic, Ambient

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September 11 @ The Old Church Concert Hall – Golden Retriever began with a focus on the relationship of two primarily monophonic instruments.

Win Tickets ($40): Four-Eyed Horsemen w/ MC Lars @ Lola’s Room | Hip Hop, Rap, Featuring Mega Ran, MC Frontalot, Schaffer the Darklord

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September 5 @ Lola’s Room – MC Lars is the creator of post-punk laptop rap and lit-hop, which he has extended and powered into a fusion of rap, punk, rock, ska, pop and other genres.

Win Tickets ($30): Weathers “Our Little Secret Tour 2021” @ Lola’s Room | with Aaron Taos, Stylish Cool Alt-indie

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October 20 @ Lola’s Room – Weathers is Cameron Boyer, guitarist Cameron Olsen, bassist Brennen Bates, and drummer Cole Carson, creating alternative, indie rock.

CANCELED: Trio Subtonic w/ Dan Balmer @ The Goodfoot Pub & Lounge | Groove Heavy Funk, Soul Jazz, Portland 2021 Labor Day Weekend

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September 4 @ The Goodfoot – Trio Subtonic is a groove heavy power trio that blends genre bending funk with slow burning underground soul jazz.

New Portland Jobs: Portland Public Schools, Columbia Riverkeeper, Doug Fir Lounge & More! | August 24, 2021

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Here are the latest Portland job listings on PDX Pipeline for the week including Laundry Care, Leatherman, NEEA & More!

Win Tickets ($80): Gogol Bordello @ Crystal Ballroom | Gypsy-Punk Rock, Featuring Special Guests

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August 29 @ Crystal Ballroom – Gogol Bordello has spent over a decade electrifying audiences the world over with its internationally acclaimed gypsy-punk sound.

Win Tickets ($50): The Milk Carton Kids & Haley Heynderickx @ Revolution Hall | Singer/Songwriter, Indie Folk

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September 9 @ Revolution Hall – Listening to The Milk Carton Kids — Joey Ryan and Kenneth Pattengale — talk about their creative process, it’s easy to imagine them running in opposite directions even while yoked together.

SE Portland Pie Bake Off @ Moreland Farmers Market | Benefit for Double Up Food Bucks, Free Pie Spices

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Show off your favorite pie recipe by entering it in Moreland Farmers Market Pie Bake Off on September 1, 2021.

CANCELED: An Evening With George Winston @ Aladdin Theater | Rural Folk Piano

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September 11 @ Aladdin Theater – George Winston is undeniably a household name. He’s inspired fans and musicians alike with his singular solo acoustic piano songs for more than 40 years while selling 15 million albums.

Win Tickets ($130): Revolution Hall Presents The Monkees Farewell Tour with Michael Nesmith & Micky Dolenz | All The Hits & Fan Favorites

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September 12 @ Revolution Hall – “The Monkees Farewell Tour” will feature songs that span the band’s entire career – from their 1966 self-titled debut album to 2016’s Good Times!

August Willamette Flea Market in NE Portland | Vintage, Collectibles, Makers Artists, Food & More!

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August 28 @ Shilo Inn – Shop the Willamette FLEA for a delightful adventure supporting local micro-businesses.

Win Tickets ($34): Circles Around The Sun, w/ Frank LoCrasto @ Aladdin Theater | Rock, Indie, Roots

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September 10 @ Aladdin Theater – Los Angeles-based instrumental supergroup Circles Around the Sun returns with the release of their self-titled, third full-length studio album, Circles Around the Sun.

Win Tickets ($50): Haley Heynderickx & The Milk Carton Kids @ Aladdin Theater | Singer/Songwriter, Indie Folk

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September 8 @ Aladdin Theater – Listening to The Milk Carton Kids — Joey Ryan and Kenneth Pattengale — talk about their creative process, it’s easy to imagine them running in opposite directions even while yoked together.

MANY Portland Weekend Events & Giveaways: Parkrose Marketplace, Stoolhumpin’ Comedy Show, Sangria Saturday, Summer Shindig & More! | August 19-22, 2021

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The weekend is back, Portland! Parkrose Marketplace features live music & vendors. Hip Chicks Do Wine is hosting Sangria Saturday and Rose City Rollers will have skating at the waterfront. And the weather should be perfect for a Portland Spirit cruise.

Portland in the News: Outdoor Dining Permits Extended; City Growth Outpaces State; Portland Grown African Produce & More! | August 19, 2021

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PBOT has extended permits for outdoor dining areas through June of 2022.

Census numbers show Portland’s population growth has outpaced Oregon’s over the last decade.

And a family owned farm in North Portland is growing African produce that you can’t find in a grocery store.

Protectly’s Mask Recommendations | What is the Best KN95 or N95 Mask for Covid-19?

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KN95 and N95 masks (also known as respirators) are more protective than surgical masks and cloth masks.

New Portland Jobs: SeatGeek, Widmer Brothers Brewing, Albertina Kerr & More! | August 17, 2021

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Here are the latest Portland job listings on PDX Pipeline for the week including Reed College, Aria HR, Bella Organic Farm & More!

CANCELED: The Cooky Jar With DJ Cooky Parker and DJ Void @ The Goodfoot Pub & Lounge | Classic R&B, Soul & Funk

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August 28 @ The Goodfoot Pub & Lounge – DJ’s Cooky Parker (Ural Thomas & The Pain) and Void bring you a hot summer’s eve of soul, classic R & B and funk. Bring your dancing shoes with you tonight!

2021 Easterseals Walk, Run & Roll Benefit @ Oregon Zoo | Live Music, Scavenger Hunt, Costume Contest

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Easterseals Oregon presents the inaugural in-person Walk, Run, & Roll benefit at the Oregon Zoo on August 28.

2021 August Parkrose Marketplace | Raffle, Live Music, Food, Drink Garden, Vaccines, Arts & Crafts & More!

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August 21-22 – Parkrose Marketplace has live music, great food, beverage garden put on by Catman Cellars winery and Level Beer Brewery, local-indigenous-global art and craft, clothing, jewelry, handcrafted treasures of all kinds.

MANY Portland Weekend Events & Giveaways: Sand Island Sand Castle Competition, Beaverton Night Market, Scappoose Centennial, T.E.A.M. Market & More! | August 12-15, 2021

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The weekend is back, Portland! It’s Friday the 13th — celebrate w/ a Haunted Pub Tour or Halloween in August! Shop from more than 85 curated designers at Unique Markets Summer Pop Up. And cool off after the heat wave w/ Hip Chicks Do Wine’s Corks & Cones.

BeerQuest Friday the 13th Haunted Pub Tour in Downtown Portland | Award-Winning Beer + Meet Ghosts of Old Town

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August 13 in Downtown Portland | Join BeerQuest Walking Tours for a historical journey into Portland’s wicked and lawless past. 

Portland in the News: Cooling Centers; Hottest in SE Portland; Masks Required Starting Friday & More | August 12, 2021

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Once again, masks will be required indoors throughout Oregon starting Friday. Here’s what to expect at music venues.

It may feel hot where you are, but it’s always hotter in Lents.

And as temperatures soar today and Friday, be sure to have a plan in place to keep cool or head to a cooling center.

RAM Cellars Summer Shindig & TLDEF Fundraiser @ Hip Chicks Do Wine | Pouring a Special Curated Lineup of 8 Wines

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On Sunday, August 22nd, from 5pm to 8pm, RAM Cellars is throwing our Summer Shindig and TLDEF Fundraiser at Hip Chicks Do Wine.

New Portland Jobs: Bulk Bookstore, Point West CU, Tender Loving Empire & More! | August 10, 2021

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Here are the latest Portland job listings on PDX Pipeline for the week including Basic Rights Oregon, Portland Piano International & More!

Win Tickets ($30): Lost Ox @ The Goodfoot Pub & Lounge | Jamband, Outlaw Funk, Americana, Progressive Rock

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August 21 @ The Goodfoot – Jamband aficionados Lost Ox have been unleashing their uniquely progressive brand of outlaw funk & Americana upon the once unsuspecting public since 2017.

Win Tickets ($50): Shannon and the Clams @ Crystal Ballroom | Retro-rock Band, Featuring Paranoyds & Roselit Bone

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September 4 @ Crystal Ballroom – Year Of The Spider, Shannon and the Clams ‘s sixth studio album, rages against death and disease with the power of a thousand angry Ronettes.

Set Apart Your Next Virtual Work Meeting w/ hello curated | Custom Gift Kits to Elevate Online Experiences

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Set your virtual events apart by offering elevated gifting experience collections for your next virtual gathering with staff, colleagues, or clients.

MANY Portland Weekend Events & Giveaways: Art in the Dark, Roughstock Rodeo, Flamenco Friday, Outdoor Skating, Goodfoot Music & More! | August 5-8, 2021

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The weekend is back, Portland! Look to the trees as A-WOL Dance Collective presents Art in the Dark. Flamenco Fridays Returns to Bar Vivant. And live shows are BACK at The Goodfoot Pub & Lounge – Enter to WIN TICKETS!

Portland in the News: Slow Streets Made Permanent; Rooftop Bars; The History Under Our Feet & More | August 5, 2021

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Many of the city’s temporary slow streets will be made permanent as at least 80 blocks will have permanent concrete barriers installed.

The sidewalks of SE Portland tell an interesting history.

Now’s a great time to check out Portland’s rooftop bars.

THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!

A round up of what's going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!

Win Festival Passes ($950) Pickathon 2026 @ Pendarvis Farm in Happy Valley, OR | Indie Music Festival

Pickathon 2026 is back at Pendarvis Farm in Happy Valley, Oregon, July 30 through August 2. Now in its 26th year, this beloved Portland-area festival brings together legends and rising stars across four magical days in the woods.

Happy Hour Sightseeing @ Portland Spirit | Food, Drinks, + River Sailing

Perfect for a happy hour on the river with friends, a family adventure or visitors scoping out Portland for the first time.

McMenamins Presents 7DS: The Absolute Worst Show: Worst. Vacation. Ever @ White Eagle Saloon | Interactive Open Mic Comedy & Storytelling

The Absolute Worst is an interactive, open-mic comedy/storytelling show where audience members face off against three curated comedians and storytellers to find out who can lay claim to having lived the worst love story ever, with both absolutely fabulous and absolutely terrible prizes at stake.

Win Tickets ($44) McMenamins Presents Coda (Led Zeppelin Tribute) @ Mission Theater | Rock & Roll

CODA is a Seattle-based Led Zeppelin tribute super group with a cast of 6 world class musicians.

Portland in the News: Angry Birds, Sidewalks Sparking Joy, Fleet Week Delays & More | June 4, 2026

Is your sidewalk sad? A Portlander has a tutorial on creating your own 'sidewalk joy' project. 

2026 White Lotus Summer Market @ Fubonn Shopping Center | FREE, AAPI Food Vendors, Artists & More

The White Lotus Summer Market returns as Portland’s premier multi-weekend outdoor market experience, bringing together food, culture, and community across four consecutive weekends.

Wine Wednesdays @ Négociant | Weekly Wine Flights & Tastings

A weekly flight of wines centered around a theme, whether that is a grape varietal, a producer, a region, a style of winemaking or sometimes just the crews’ favorites.

Win Tickets ($81) McMenamins Presents Little Stranger w/ Tropidelic & Jarv @ Crystal Ballroom | Alt Indie Hip-Hop

Hailing from Philadelphia and now based in the vibrant city of Charleston, SC, alt indie hip-hop duo Little Stranger (Kevin and John Shields, no relation but best friends) have spent years honing their signature sound and perfecting their version of the 'organized chaos' that a Little Stranger live show entails.

Win Tickets ($22) McMenamins Presents Decadent 80s Dance Party @ Crystal Ballroom | Portland’s Longest Running 80s Night

Get ready for a fun night of dancing to all your favorite hits and requests from the 1980s!

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