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!

Wine Wednesdays @ Négociant | Weekly Wine Flights & Tastings

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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

Stumptown Stages presents Tootsie @ Winningstad Theatre | Musical Comedy Based on Hit Film

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Stumptown Stages closes its 20th Anniversary Musical Season with the comedy musical Tootsie. Based on the hit comedy film starring Dustin Hoffman and ranked as one of the best comedies of all-time

Escapism Portland Presents The Wizard’s Lair | Unravel the Wizard’s Secrets of Alchemy

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A master wizard has spent the last several months cloistered in his hidden lair before finally vanishing completely.

Alice in Wonderland Teas @ Victorian Belle | Sweet & Savory Bites Paired w/ Teas

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The Victorian Belle’s Alice in Wonderland-themed Afternoon Teas are a fun and elegant way to celebrate in March! Don your best top hat or fascinator and enjoy an afternoon inspired by the whimsy of Wonderland.

Win Tickets ($70): Timecop1983 @ Mission Theater | Synthwave

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Timecop1983 is a producer from Eindhoven in The Netherlands. His style is best described as romantic and cinematic, inspired by the 80’s.

Win Tickets ($44): BACKFENCE MIXED MEDIA Storytelling presents ‘Am I The Villain?’ @ Powell’s | Visuals, Music, Poetry

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BACKFENCE MIXED MEDIA Storytelling brings you true stories based on the theme ‘AM I THE VILLAIN?’: Personal stories told with visuals, live music, via poetry, video, and a tasty new choral story format.

Murder Mystery Dinner @ Victorian Belle | Til Death Do Us Part: All is Fair in Love and Murder!

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The birds are chirping, and the sun is shining, but the wedding bells aren’t ringing for this not-so-happy couple when a member of the wedding party is murdered!

Win Tickets ($80): Gusi @ Mission Theater | Latin Grammy Nominee, Pop, Colombian Folk

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March 31 @ Mission Theater – Gusi’s inaugural USA tour will create unforgettable moments with his audience. This journey is about deep connections and unique experiences.

Win Tickets ($40): Jesse Dayton @ Mission Theater | American Roots, Texas Blues

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Jesse Dayton lives and breathes American roots music, blending Texas blues, honky-tonk swagger, and punk-rock grit into an electrifying live show.

Portland in the News: Warm Days, Exoplanets, Giant Lions & More | February 27, 2025

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What does a giant chrome lion, Taylor Swift and Broadway have in common with Portland?

Latin Rock Exchange @ Mississippi Pizza Pub – Atlantis Lounge | Latin Rock, Jazz, RnB

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Latin Rock Exchange plays Latin rock classics that we all know and love from Santana, War, Barrabas, Yesca, The Buena Vista Social Club, Jobim, and contemporary hits

Portland to Astoria River Cruise @ Portland Spirit | All-Day Cruise, Historic Narration, Food

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The broad waters of the Columbia River will carry you from Portland’s vibrant harbor through the forest covered coast range on an adventure filled day retracing the route of Lewis & Clark.

Win Tickets ($16): Super Secret Band @ The Goodfoot | Funky, Spacey Sounds

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Join us for night one of a three-Thursdays-in-a-row residency with Super Secret Band.

Win Tickets ($88): exes and o’s Live w/ Shannon Beveridge @ Aladdin Theater | Queer Relationship Podcast

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Recognizing the need for diverse representation in entertainment, Shannon has made it her mission as a storyteller to represent the LGBTQIA+ community through her work.

2025 Spring Improv Classes @ Deep End Theater | Scene Study, Ensemble Improv & More

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Our March through April session is packed with four amazing classes.

Forest Pub @ Mission Theater | Building the New PDX Airport with Local Mass Timber

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Join our friends from the Port of Portland and project partners to hear stories behind the design, construction, and sourcing of the new main terminal at Portland International Airport.

Win Tickets ($72): David Nihill: Shelf Help @ Aladdin Theater | Comedy + Reading Recommendations

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Leaving Dublin, Ireland where he was born and raised until the age of 22, David got drunk on travel and never quite hit sobriety of it.

Win Tickets ($50): And That’s Why We Drink @ Revolution Hall | Comedy, Paranormal, True Crime

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Hosted by New York Times best selling authors Em Schulz and Christine Schiefer, “And That’s Why We Drink” is an award-winning comedy podcast, where the paranormal and true-crime meet.

Win Tickets ($105): Asleep at the Wheel @ Aladdin Theater | Grammy Award-Winning Swing Music

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For over fifty years, Asleep at the Wheel’s Ray Benson has been traversing the globe as an ambassador of Western swing music and introducing its irresistible sound to generation after generation.

Women of Nob Hill Walking Tour @ Slabtown Tours | Women’s History Month

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You will explore a section of the Alphabet Historic District from grand homes to vintage street car commercial structures focusing on the women who lived and or worked in the neighborhood.

Portland’s Alternative Wedding Fair @ Rae Loft | Plan Your Celebration

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Browse local alternative companies who don’t say “I do” to the traditions of older times.

2025 Winter Music Festival @ Milwaukie Elks Lodge | 2 Stages, 6 Bands

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As the new year gets off to a start, people are making their resolutions. If one of them is to go to more festivals, you won’t have to wait until summer to achieve that.

2025 Shamrock Cruise On The Portland Spirit | Irish Music + Dancing, Food, Full Bar

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The 8th annual Shamrock Cruise will board at the Caruthers Street with free and secured parking on Sunday, March 16, 2025.
Come enjoy the annual Shamrock Cruise onboard the Portland Spirit for a three-hour cruise on the Willamette from 4-7pm with the music and dance of Ireland all communities and ages.

Mt Hood Repertory Theatre presents Silent Sky @ OMSI’s Kendall Planetarium | Celestial Visuals, Live Music

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Mt Hood Repertory Theatre is producing Silent Sky by Lauren Gundersen in partnership with OMSI.

Last Thursday Art Opening @ The Goodfoot | Featuring: Alan Rose, Brett Bowers, Ian Jankowski-Seniff

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The Goodfoot will have an art opening last Thurs Feb 27th. the show will be up until March 23rd.

2025 Oscar Trivia & Viewing Party @ The EastBurn Public House | Shanrock’s Trivia, Prizes, Costumes

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It is time for our annual Oscars shenanigans!

Win Tickets ($44): Sydney Sprague w/ Pony @ Mission Theater | Indie Pop

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Sydney Sprague channels her sadness, anxiety, and existential dread through driving guitars, shimmering melodies, and the deceptively sweet weapons of indie pop-rock and keen observation.

Free Improv Workshop @ Deep End Theater | Lead by Domeka Parker (Artistic Director)

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Join us for a fun afternoon of play! In this workshop we will dip our toes into Deep End’s unique improv style.

Portland in the News: PDX Jazz Festival, Baby Elephant, Timber Jim & More | February 20, 2025

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In case you need a pick me up, Oregon Zoo’s newest elephant calf Tula-Tu will be on display to visitors for the first time this Friday.

Clash of the Trivia Titans @ Spare Room | Shanrock’s Triviology 20th Anniversary

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This is the Super Bowl of trivia; the Oscars of pub quizzery…there will be one team to rule them all!

Win Tickets ($87): Bruce Cockburn @ Aladdin Theater | Folk, Jazz, Rock

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Bruce Cockburn’s latest studio album, O Sun O Moon, is a testament to his enduring artistry, even as he nears his 78th birthday.

Portland’s Pettiest Drag Show @ Escape Bar & Grill | Hosted by Savannah O Bennington

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Portland’s Pettiest Drag Showcase, featuring some of your Favorite Local Drag Performers. Hosted By Savannah O Bennington.

Artists Repertory Theatre presents Sapience | By Diana Burbano, Directed by Melory Mirashrafi

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Elsa is a primatologist studying the language abilities of orangutans, like her subject Wookie who yearns for connection with humans.

Win Tickets ($54): An Evening with Fink @ Aladdin Theater | Music has been featured in The Walking Dead, True Detective

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Fink, AKA Fin Greenall, is a singer-songwriter from Cornwall, UK, currently based in Berlin.

Win Tickets ($87): Bored Teachers: The Struggle is Real Comedy Tour @ Revolution Hall | #1 Ranked Teacher-Comedy Podcast

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Bored Teachers are BACK with all new material on their “The Struggle is Real!” Comedy Tour.

Win Tickets ($52): Matt Braunger @ Aladdin Theater | ABC’s Agent Carter, NBC’s Up All Night, Comedy

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Matt Braunger was raised in Portland, Oregon. A headlining comedian since 2007 and an actor since childhood, Matt studied theatre in New York and improvisation in Chicago.

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 Tickets ($42): Line ‘Em Up – Queer Line Dancing @ Crystal Ballroom | Dance Lessons w/ Stomptown

September 12 - Join Stomptown, Portland's LGBTQ+ Country Western dance hub, for an exhilarating night of non-stop line dancing.

2026 Swan Island Dahlia Festival | 50 Acres of Blooms, Food Carts, Live Music

We invite you to celebrate the season of Dahlias! Stroll through almost 50 acres of breathtaking fields and a beautiful display garden of stunning dahlias featuring over 375 varieties.

7 Deadly Sins Pants On Fire Family Friendly Show @ White Eagle Saloon | Seven True Tales, One Lie

September 19 - Join us as we host Portland's wildest and most interactive comedy and storytelling entertainment event with Pants On Fire! at the historic White Eagle Hotel & Saloon. 

Win Tickets ($130): Portland Weird Fest @ Oaks Park | 60+ Vendors, Rides, Live Bands, Costume Contest & More

September 19 - Portland Weird Fest is back for Year 3 — and Portland is about to get wonderfully weird!

Win Tickets ($136): Dogstar w/ The Backfires @ Crystal Ballroom | Keanu Reeves, Alt-Rock

September 17 - Let the record show that here in 2026, Dogstar is clearly All In Now.

Win Tickets ($92): Marc Price @ Mission Theater | Comedy, Star of ‘Trick or Treat’, ‘Family Ties’

September 21 - Marc, best known as Skippy from the beloved 80's sitcom Family Ties, is a multi-talented performer who has conquered the worlds of stand-up comedy, acting, hosting, and even writing and producing.

Win Tickets ($22): Decadent 80s w/ DJ NoN @ Crystal Ballroom | Portland’s Longest Running 80s Night

September 11 - Get ready for a fun night of dancing to all your favorite hits and requests from the 1980s!

2026 Cannon Beach Cottage Tour | Self-Guided Walking Tour of Beautiful Homes, Opening Night Bash

September 11-13: Discover the charm, history, and beauty of one of the Oregon Coast's most beloved traditions during the 23rd Annual Cannon Beach Cottage Tour!

2026 Time-Based Art Festival @ Portland Institute for Contemporary Art | Experimental Performances, Live Music, Dance & More

September 9-13 - This year’s festival brings artists and audiences together for its annual celebration of creative expression that can best be experienced together, in the present moment.

Lake Oswego Clean Energy and EV Fair @ Lake Oswego United Methodist Church | Test Drive EVs, Learn About Solar, Batteries & More

September 19 - The fair is a fun, family-friendly event celebrating clean transportation, renewable home energy and sustainable living.

Win Tickets ($42): Valkerie w/ Withholden, Laughing About Nothing, Fawkes Glove @ Mission Theater | Alternative Rock

September 25 - In their second project, Myocardia, we meet the alternative rock four piece, Valkerie, after accumulated break ups, heart conditions, and deaths.