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!

Shanrock’s Triviology presents Clash of the Trivia Titans @ Dots Cafe | 21st Anniversary, Prizes

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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!

Portland Gay Men’s Chorus presents Encores! @ Magenta Theater in Vancouver WA | Intimate Vocal Showcase & Benefit

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Encores! pulls back the curtain on the Portland Gay Men’s Chorus to spotlight the remarkable talents you don’t always get to see on the mainstage.

FREE Improv Workshop @ Deep End Theater | A Fun Afternoon of Play

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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.

Win Tickets ($160): Portland Opera presents Fellow Travelers @ Newmark Theatre | Lavender Scare of McCarthy Era

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A powerful and deeply moving historic snapshot, Fellow Travelers is set amidst the Lavender Scare of midcentury McCarthyism, when persecution of LGBTQ+ people within the Federal government was rampant.

Win Tickets ($90): Flanagan’s Wake @ Experience Theatre Project | Interactive Irish Comedy, Improv, Live Piano

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Grab a pint and enjoy one of the funniest Irish shows that you’ve never heard of!

Mt. Hood Repertory Theatre presents The Life of Galileo @ OMSI Kendall Planetarium | Live Music, Celestial Visuals

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The Life of Galileo by Bertolt Brecht recounts the true story of astronomer Galileo Galilei, a key figure in the 17th-century Scientific Revolution.

Bunk After Dark @ Bunk Bar | Live Comedy Game Show

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Bunk After Dark is a live comedy game show where two teams of comedians go head-to-head in a fast-paced laugh-off packed with improv challenges, wild prompts, and audience participation.

Wine on the Water Cruises @ Portland Spirit | Wine Tasting Sunset Cruise

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Taste your way through Oregon on this sunset wine tasting cruise aboard the Portland Spirit!

Ladies Night Out @ Club Privata | PNW’S Premier Lifestyle Club

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Everyone is welcome at this special night so dress to impress and step into a world where the men perform for the ladies.

Portland in the News: Bad Bunny Couple’s Oregon Connection, 100 Years of Hollywood Theatre & More | February 12, 2026

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Before Thomas Wolter and Eleisa Aparico tied the knot at Bad Bunny’s Super Bowl half-time show, they were engaged in Cannon Beach. 

Boom Arts presents WAYQEYCUNA by Tiziano Cruz @ Ellyn Bye Studio | U.S.Premiere Performance from Argentina

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Boom Arts is proud to present the National Premiere of Wayqeycuna, a new one-man show by queer, Indigenous, Argentine artist Tiziano Cruz. 

Mardi Gras – Kasidie Night @ Club Privata | PNW’s Premier Lifestyle Club

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Celebrate Mardi Gras at Club Privata! Indulge in the fantasy where masks, beads, lace, and barely-there looks set the tone.

2026 Valentine’s Day Weekend @ PAM CUT’s Tomorrow Theater | You’ve Got Mail, Hairspray, Crafternoon & More

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This weekend, we’re celebrating all types of love! 💖 From friends turned lovers in Rob Reiner’s When Harry Met Sally… to love of friends and crafting at Romy and Michele’s High School Reunion Crafternoon.

Michelle Buteau: The Surviving and Thriving Tour @ Arlene Schnitzer Concert Hall | ‘Survival of the Thickest’, ‘A BUTEAU-FUL MIND’

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Michelle Buteau is an actress, comedian, producer and writer. The multihyphenate stars in the Netflix comedy series “Survival Of The Thickest”, which she created and executive produced.

Free Portland Trivia w/ Bridgetown Trivia | Sundays-Thursdays, Prizes

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Bridgetown Trivia is your neighborhood pub trivia game done right.

2026 Portland Valentine’s Day Weekend Events | Festivals, Chocolate, Wine, Dinner, Markets & More

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In 2026, Valentine’s Day falls on a Saturday so there will be events all weekend.

Win Tickets ($80): FIA @ Crystal Ballroom | R&B, Soul, Reggae

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FIA is a five-time Island Music Award winner from Nanakuli, Hawai’i, known for blending R&B, soul, and reggae into a style that connects across generations.

2026 Biamp Portland Jazz Festival | 50+ shows, 30+ venues feat. St. Vincent, Mavis Staples & More

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Tickets on sale now for the 2026 Biamp Portland Jazz Festival! The most artistically diverse lineup yet with 50+ shows across 30+ venues.

Eras in a Glass: A Taylor Swift Wine Pairing @ Hip Chicks Do Wine | 6 Wines Inspired by Taylor Swift Songs

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Calling all Swifties! Join us at Hip Chicks do Wine on Friday, February 28th from 2pm–5pm for an afternoon of wine, food, and Taylor-inspired fun.

Wine Wednesdays @ Négociant | Weekly Wine Flights & Tastings, Valentine’s Day

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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.

Portland in the News: Black History Month Reads, Goodbye Lloyd Center, Beyond Dry January & More | February 5, 2026

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February is Black History Month and the Multnomah County Library has a list of graphic novels by black authors to check out. 

Bloody Valentine VHS Swap & Market @ Dots | Bachelorx Auction, DJ Black Planet

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Saturday Feb 7th, we have our next VHS Swap and Vendor Market. We have a ton of awesome tape vendors this time around, so you definitely don’t want to miss it.

Portland Winter Light Festival 2026 | 9 Days of FREE, Outdoor Winter Art Across The City

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PDXWLF brings art, technology, and inclusivity together, invigorating Portland in the winter.

Amanati @ Nova PDX | Exotic Electronic Music

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Amanati, godfather of Exotic Electronic Music, is a symbol of creative power, raw expression, sensuality, and freedom.

Toxic Love @ Darcelle XV Showplace | A Drag & Cabaret Revue

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RAE presents this ICONIC Drag & Cabaret, featuring some of your Favorite Local Drag Performers in Portland at Darcelle XV Showplace!

Friday Night Magic: The Gathering @ The EastBurn Public House | Join the Battle!

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Shuffle up and let the Magic happen. Come sit in with us for Friday Night Magic. A night of games, good energy, and people who truly support the community.

Win Tickets ($34): 2026 Portland Spring Home and Garden Show @ Portland Expo Center | Showcase Gardens, Floral Fashion Show, Chef Demos

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For decades, this beloved event has brought together garden enthusiasts, design lovers, homeowners, remodelers, and local makers, offering fresh ideas, expert advice, and the latest home and garden trends for every skill level.

Weird Portland Pub Tour: Valentine’s Edition in SE Portland | Great Beer + Weird Stories

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Looking for a Valentine’s outing that’s anything but ordinary? This is the tour for people who love great beer, weird stories, and Portland’s wonderfully offbeat personality.

Heartbreakers: A Draglesque Love Story @ Echo Theater Company | Love & Lust Inspired Drag/Burlesque

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RAE presents this ICONIC Love & Lust Inspired Draglesque Showcase.

Alphaboats: A Maritime Voyage from Anchor to Zulu @ Columbia River Maritime Museum in Astoria | Mixed Media Paintings

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Set sail on an alphabetical journey through the world of boats in Alphaboats: A Maritime Voyage from Anchor to Zulu, a vibrant mixed-media exhibition by Portland artist Peggy Biskar.

Jade Rabbit x Veganizer 2026 Lunar New Year Banquet | Six Course Menu of Lunar New Year Delicacies

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Join us as we usher in the Year of the Fire Horse with a six course menu of Lunar New Year delicacies.

Blueprint Ensemble Arts presents Shadow & Light | FREE, Live Music, Dessert

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Come join ensembles Carnation, Peach, Scarlet, and Burgundy (with special guests Ivory and The Super Cuts) as they bring you our upper voices masterwork for 2026: Arnesen’s stunning Stabat Mater!

Drag Brunch @ The Pharmacy | Hosted by Devlin Lynn Phoenixx

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The event is hosted by Rose Empress LXV, Devlin Lynn Phoenixx with a rotating cast for each event sure to dazzle you with their everything!

2026 Valentine’s Day Dinner @ The EastBurn Public House + Anti-Valentine’s Day Party | Dinner, Brunch, Specials

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Celebrate your sweetie with brunch, dinner and drinks in the beautiful EastBurn dining room!

Win Tickets ($56): Jeremy McComb’s Honky-Tonk Circus @ Mission Theater | The #1 90’s Country Music Experience

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The Honky-Tonk Circus Tour isn’t a throwback – it’s a full-throttle time machine to the nights when country music ruled the room.

Win Tickets ($80): Heated Rivalry: A Jockstar Rave @ Crystal Ballroom | A Night of Party Boy Anthems & Club Hits

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From the Closet → Ice → Dance floor.

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!

Portland in the News: Waterfront Restaurant, Airport Accolades, Heatwave & More | June 11, 2026

The Portland Spirit has big plans to open a new restaurant in the former Rose Festival headquarters in Tom McCall Waterfront Park. 

McMinnville Art Festival @ Downtown McMinnville | 50+ Artists & Artisans, Interactive Kids’ Crafting, Art Demos, & More

July 18-19 - Celebrate creativity in the heart of Oregon wine country at the McMinnville Art Festival, a free two-day outdoor event showcasing the work of talented artists and artisans from across the region.

PRIDE at the Museum @ OMSI | A night at the museum celebrating the LGBTQ+ Community

June 12 - Celebrate PRIDE at the Museum with an evening of science, community, and joyful exploration!

Villain Arts Tattoo Festival @ The Rose Quarter | Celebrate the Art of Tattooing

July 17-19 - Tattooing is more than body art—it’s a global language of identity, resilience, and self-expression.

New Portland Jobs: Portland Fire, Clark County Fair, Bend Chamber of Commerce & More

New Portland Jobs: Portland Fire, Clark County Fair, Bend Chamber of Commerce & More!

Win Tickets ($92): McMenamins Presents Justin Nozuka @ Mission Theater | Folk, Rock + R&B

October 20 - Justin Nozuka is a singer-songwriter and producer born in Queens, New York and raised in Toronto, Canada.

7 Wonders of the Gorge @ Portland Spirit | Jet Boat Cruise, Majestic Views

Experience some of the most majestic views of the lower Columbia River Gorge visible by water aboard the Explorer Jetboat!

Bigfoot Adventure Cruises @ Portland Spirit | Learn the History of Bigfoot on a Jetboat

On this Columbia River boat tour, you'll explore the history and lore of Bigfoot while traveling 80 miles roundtrip on a high-speed jetboat from Portland to Multnomah Falls.

Watch 2026 World Cup Games @ Sticky Wicket | 7 TVs, 16 Taps, POG Shots

Watch World Cup games with 7 TVs (sound on upon request), 16 taps (beer, draft cocktails, cider, seltzer, and one NA IPA). Have a "POG Shot", a passionfruit, orange, and guava shot that includes rum.

Win Tickets ($46): McMenamins presents Holi Summer Fest: A Celebration of Color @ Grand Lodge in Forest Grove, OR | Organic Colors, Bollywood & Bhangra Dance Party

HOLI HAI! After four sold-out Holi Festivals Anjali & The Kid bring their color throw experience to Forest Grove for their biggest Holi yet featuring all organic colors handmade by farmers and tribal communities in India.

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