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!

2026 Portland Dining Month | 3 Course Meals, 2 Price Options, 100+ Restaurants

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More than 100 of Portland’s most celebrated restaurants are offering 3 course meals at $35 and $55 for all of March.

Outdoor School Benefit Concert @ Mission Theater | Live Music feat. Kaia Müller, The Wild Lilacs & More

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Join the Outdoor School community to hear amazing performers share their music in celebration of Outdoor School.

Columbia River Maritime Museum presents Salt & Spirit – A Maritime Tasting Voyage @ Pilothouse Distilling in Astoria OR | Taste Sea-Aged Whiskeys

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Taste three Whiskeys that were aged at sea while learning about the vessels who took them out!

Beaverton Symphony Orchestra presents Double Vision | 2 Marvelous soloists, 3 Legendary Composers

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An intimate concert with grand appeal, Double Vision features two world-class soloists and three legendary composers.

Portland in the News: Truffle Dogs, Coastal Snow, Ice Age Artifact & More | February 19, 2026

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Who has four legs, a wet nose and a skill for sniffing out expensive fungi? The competitors of the Joriad Truffle Dog Championship, which took place earlier this month in Eugene. 

Win Tickets ($30): Nosferatu (1922) Silent Film with Live Music By: MLTZR @ Mission Theater | Electronic, Jazz

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Experience the silent film classic, Nosferatu (1922) accompanied by live music and sound effects by Portland, Oregon based musician MLTZR.

River Rhythms @ Portland Spirit | Friday Dinner Cruises w/ Live Vocalists

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On Friday nights through April 24th, you can enjoy the talents of local professional vocalists during your three-course dinner cruise.

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.

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!

Scooped Ice Cream Festival @ Esther Short Park in Vancouver, WA | 50+ Flavors of All You Can Eat Ice Cream

July 18-19 - The Pacific Northwest's premier ice cream festival is back at Esther Short Park in Vancouver, WA for two all-you-can-eat days of scoops, live music, and summer fun. Scooped! returns July 18 and 19, 2026, 11:00 AM to 7:00 PM — and your ticket includes unlimited ice cream from 50+ flavors served up across Scoop Valley.

Chamber Music Northwest presents CONFLUENCE: Our Shared Voices 2026 Summer Festival | 70 of the world and our region’s finest chamber musicians!

Music has the ability to connect us beyond words, labels, and borders, inviting us to celebrate both our differences and our common ground.

Tea Fest PDX @ World Forestry Center | A Celebration of Tea Culture

June 27 - TeaFestPDX is more than a festival, it’s a community.

St. Helens Independence Day Celebration 2026 @ Columbia View Park | Music, Food, and Activities for All Ages

July 4 - Celebrate the Fourth of July at Columbia View Park in St. Helens, Oregon – one of the most scenic Independence Day destinations in the Pacific Northwest.

Win Tickets ($160): 2027 Portland Folk Festival @ Crystal Ballroom | 30+ Local & National Artists

January 30 - An annual celebration of folk and Americana music showcasing 30 local and national artists hosted by the historic Crystal Ballroom.

Win Tickets ($86): McMenamins Presents Madison Ryann Ward @ Mission Theater | Contemporary Christian, Pop + R&B

September 4 - Faith-based singer/songwriter Madison Ryann Ward writes warmhearted songs that mix mature pop and contemporary R&B with accents of gospel, blues, and folk.

Win Tickets ($70): McMenamins Presents “A Hot August Night” with Super Diamond @ McMenamins Grand Lodge in Forest Grove | The Neil Diamond Tribute

August 22 - An uncanny tribute to beloved master singer/songwriter/performer, American pop icon Neil Diamond – Super Diamond has appeared on The Late Show with David Letterman, CNN, VH1, Fox News, and Comedy Central, and has been featured in publications such as Rolling Stone Magazine, The New York Times, and the San Francisco Chronicle.

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.

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