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!

Win Tickets ($64): James McMurtry w/ BettySoo @ Aladdin Theater | Rock, Folk

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These are some of the strange and richly drawn characters who inhabit James McMurtry’s eleventh album, The Black Dog & the Wandering Boy

Win Tickets ($60): Strings and Heart – The Plastic Wine Tour w/ Isly @ Mission Theater | Christian

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STRINGS & HEART is band of 3 brothers, Angelo, Michael and Eric Espinosa from Tucson, AZ.

Win Tickets ($30): Garcia Birthday Band w/ Shafty @ The Goodfoot | Grateful Dead & Phish Tributes

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GBB (Grateful Dead Tribute) and Shafty (Phish Tribute) combine forces for a spectacular two-night Memorial Day weekend run

Win Tickets ($22): Decadent 80s Dance Party @ Crystal Ballroom | Portland’s Longest-running 80s Night

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

Win Tickets ($50): Chokecherry w/ Instant Crush, Altar Girl, Dannie Dorko @ Mission Theater | Shoegaze, Grunge

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SF based band chokecherry is dark, black widow energy wrapped in the foil of our generation.

The Nature Ten Minute Play Festival @ Alberta Abbey | 6 Plays + Live Music

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The Ten Minute Play Festival is the cornerstone of that mission. Produced two to three times per year, every festival features a new theme.

Skinny Dip @ Deep End Theater | Open Stage Variety Show

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From improv to singers, actors, musicians, poets, comedians, magicians, you never know what you will see on any given night.

Portland in the News: Blazers Up for Sale, Hollywood’s Film District, Summer Splash Pad & More | May 15, 2025

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Do you have a few billion dollars laying around? The Portland Trail Blazers are officially for sale!

Win Tickets ($124): Henry Cho: The Empty Nest Tour @ Revolution Hall | Comedy

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On February 11, comedian Henry Cho was inducted as the 229th member of The Grand Ole Opry. This prestigious honor has not been extended to a comedian since 1973.

2025 Portland Memorial Day Weekend @ Hip Chicks Do Wine | BBQ + Wine Tastings

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Kick off your Memorial Day Weekend with a deliciously fun and flavorful event at Hip Chicks Do Wine!

Win Tickets ($140): Grateful Dad Father’s Day Run @ Springwater Corridor Trail | Half Marathon, 10k, 5k or Kids Run

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Whether you run together as a family or ready to crush a Half Marathon yourself, make the Grateful Dad a Father’s Day weekend tradition! 

Register for 2025 Wild Coast Summer Camp @ Neskowin Valley School | Study Native Plants, Develop Survival Skills & More

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Discover the adventure of a lifetime at Wild Coast Summer Camp, a summer day camp where young outdoor enthusiasts can learn essential wilderness and bushcraft skills while exploring the stunning Oregon Coast and its surrounding forests.

Win Tickets ($20): Comedy: The Musical @ Samaritan Odd Fellows Lodge | Grunge Edition

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We blend stand-up comedy with musical improv in a way you won’t see anywhere else. A comedian tells jokes, and then our musical improvisers create a brand-new, hilarious song on the spot.

Win Tickets ($128): Brit Floyd ‘Wish You Were Here’ 50th Anniversary @ Keller Auditorium | The World’s Premiere Pink Floyd Experience

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Brit Floyd, widely regarded as The World’s Premiere Pink Floyd Experience (Rolling Stone Magazine), returns to Portland on July 22nd, performing at The Keller Auditorium

Win 3-Day Pass ($299): Cascade Equinox Festival @ Deschutes County Fairgrounds | Live Music, Art, Wellness

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A portal into creativity, connection, and celebration—a festival reimagined. Cascade Equinox Festival returns to the high desert of Central Oregon for its third annual gathering

Win Tickets ($150): 2025 Filmed By Bike Festival @ Hollywood Theater | 3 Days of Bike Films

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Filmed by Bike is a touring film festival that features the world’s best bike movies.

Portland in the News: Best Olive Oil, Secret Gardens, Falstaff Goes 80s & More | May 8, 2025

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Portland’s Leach Botanical Gardens have been written up in Sunset Magazine as one of 12 secret gardens to visit in the West.

Forest Pub @ Mission Theater | Stories of the PNW Told by Tree Rings

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What can the rings of trees tell us? Cutting-edge research is revealing that tree rings hold more information than simply a tree’s age.

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.

Win Tickets ($76): Portland Cello Project @ Revolution Hall | Sunshine & Stars feat. Music of Weezer and Stevie Wonder

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Portland Cello Project brings you on an extraordinary musical journey, transforming beloved hits from Weezer and Stevie Wonder into breathtaking cello arrangements.

Win Tickets ($70): Jack & Jack @ Mission Theater | Pop-Duo

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Jack & Jack’s meteoric rise all comes down to the lifelong bond between Jack Gilinsky and Jack Johnson.

Win Tickets ($68): Neal Francis – Return to Zero Tour w/ Color Green @ Revolution Hall | Psychedelic, Rock, Indie

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The latest album from Neal Francis, Return To Zero, emerged from the kind of visionary fever dream that only the most masterful and inventive artists are capable of bringing to life.

Cappella Romana presents Passion & Resurrection | 40+ Singers, String Quartet, Bells

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Cappella Romana and In Medio form a choir of over 40 singers under the direction of Alexander Lingas to perform Ivan Moody’s powerful oratorio Passion and Resurrection.

2025 Portland Spirit Dinner Cruise & Rose Festival Opening Night Fireworks | 3-Course Dinner, Beautiful Views, Live Piano

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Watch the opening night fireworks from the observation deck of the Portland Spirit!

Rose City Rollers Bouts | Wreckers vs. Gresham Alter Egos + RCR All Stars: Wheels vs. Justice

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Rose City Rollers have an action-packed weekend of hard-hitting roller derby for you on May 16th and 17th at the Hangar at Oaks Amusement Park!

Moms & Mimosas @ Hip Chicks Do Wine | Brunch Inspired Small Plates, Wine Flights

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In addition to our regular wine flights we’ll have $10 Mimosas all weekend for anyone! You don’t have to be a Mom to get a yummy Mimosa!

Win Tickets ($56): Zia McCabe’s 50th Birthday Dream Show @ Mission Theater | Feat. Sun Atoms, Motrik, Soriah

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Portland psychedelic gaze-wave outfit Sun Atoms presents their new single ‘Take This Love’, a sonic odyssey that transports listeners to a realm of pure musical enchantment.

2025 Mother’s Day Brunch @ The EastBurn | Mimosas, Food Specials

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The EastBurn Public House is serving up mimosas, bloody marys, eggs benedict, scrambles, hash & more for Mother’s Day — No reservations needed.

Latin Rock Exchange @ Aztec Willies | 10-piece Band, Classic Hits from Santana to Pink Martini

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Latin Rock Exchange is Portland’s own ten-piece band playing classic hits from Santana to Pink Martini, War to Buena Vista Social Club

Win Tickets ($60): Stephen Stanley w/ Jake & Shelby, AP Collective @ Mission Theater | Christian, Pop

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Singer / songwriter Stephen Stanley makes music with immediate emotional impact, revealing a depth of talent that comes from years of devotion to his craft.

Win VIP Tickets ($90): Veganizer Asian Market @ Redd on Salmon | Portland’s Largest Vegan AANHPI Heritage Event

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Veganizer’s annual Asian heritage event is now bigger than ever! Eat, drink, and shop 50+ AANHPI vendors at the Veganizer Asian Market at the Redd on Salmon.

Win Tickets ($54): Phil Cook @ Mission Theater | Folk-Rock, Indie Rock

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You already know Phil Cook, at least if you’ve listened to any of the most essential folk-rock, indie rock, or even gospel records of the last decade.

Win Tickets ($42): Makeshift Casual @ Mission Theater | PDX Pop-Punk

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Makeshift Casual is the greatest band in the world named Makeshift Casual.

Win Tickets ($20): Rose Tinted @ The Goodfoot | Live Band, Sample-Based Hip-Hop

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Rose Tinted- featuring Kirk Kalbfleisch on drums, Celly on turntables, MLTZR on electronics, and Sam Arnold on bass- is a sample-based hip hop band that reproduces full band arrangements of classic hip-hop tracks.

Win Tickets ($66): 2025 Grand Lodge Brewfest | 40+ Taps, Cornhole Tournament, Live Music

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More of a megafest than a brewfest, McMenamins 3rd annual Grand Lodge Brewfest is a massive celebration of all things brewed, distilled, fermented and tasty

Win Tickets ($36): Ava Maybee ‘The Gold Star Stickers’ Tour @ Mission Theater | Indie, Pop

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Ava Maybee (23) indie/pop singer & songwriter from Los Angeles, finished top 14 of American Idol Season 20.

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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