A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
Win Tickets ($90) True West Presents Brett Dennen – Art is Life @ Aladdin Theater
Across his career, Brett Dennen has established himself as the kind of singer-songwriter who finds inspiration by digging into the nooks and crannies of the human condition—exploring pain, joy, sadness, and all points in between.
Win Tickets ($90) True West Presents Portland Cello Project: Mixtape Pop vs Grunge @ Aladdin Theater
Portland Cello Project is a genre-defying cello ensemble known for reimagining everything from Bach to Beyoncé. Based in Portland, Oregon, the group has built a reputation for pushing the boundaries of classical instrumentation by bringing cello music to rock clubs, concert halls, and festivals across the country.
Win Tickets ($10): Cascade Booksellers Association Presents Rose City Book & Paper Fair @ DoubleTree Portland | Used, Rare and Collectible Books
Oregon’s premier event for used, rare, and collectible books!
Peachy Springs’ Drag Bingo @ Holy Ghost & Advice Booth | RuPaul’s Drag Race Meets The Price is Right, Prizes
A BINGO night like no other, as a cross between RuPaul’s Drag Race and The Price is Right!
Grateful Dad Father’s Day Run @ Sellwood Riverfront Park | Half Marathon, 10k, 5K, & Kids Run
Experience the celebration, where the miles are full of dad energy, the vibes are upbeat, and every finisher celebrates with a stack of fluffy pancakes at the finish line!
Father’s Day Cruise @ Portland Spirit | BBQ Brunch, Live Music + River Views
Give Dad an unforgettable Father’s Day with a special two-hour cruise on the Willamette River.
Bra-Ha-Ha!–Benefitting Bradley Angle House @ Hip Chicks Do Wine | Bra Decorating + Movie
The Imperial Sovereign Rose Court with Rose Empress LVIII – Summer Lynne Seasons & Rose Empress LXVI – Adrienne Alexander Present…Bra-Ha-Ha! A Bra Decorating Contest! Benefiting Bradley Angle House!
Win Tickets ($38): McMenamins and World Forestry Center Present Forest Pub: Emerald Ash Borers @ Mission Theater | Science Lecture
An invasive shiny beetle is threatening Oregon’s ash trees –and the ecosystems that depend on them.
Win Tickets ($134): True West Presents Tab Benoit w/ Ghalia Volt – Soul of the Swamp Tour @ Aladdin Theater | Blues, Rock
Tab Benoit is a 4x Grammy nominated singer, songwriter and guitarist who has built a remarkable 30+ year career on the foundation of his gritty and soulful Delta swamp blues, acquiring a devoted legion of fans along the way, as well as 5 Blues Music Awards, including BB King Entertainer of the Year (twice) and an induction into The Louisiana Music Hall of Fame.
Win Tickets ($124): True West Presents Lue Elizondo – Persona Non Grata Tour @ Aladdin Theater | Science Lecture
Lue Elizondo – Persona Non Grata is a live touring theatre experience that takes the UAP conversation directly to audiences across the country.
Grillo’s PBR Release Party @ Rhinestone | Pickle Shots, Food Specials, Country Co-Op DJ Set
Come celebrate your two favorite things. Pickles & Pabst. Grillo’s Pickles & Pabst Blue Ribbon have done a limited collaboration pickle beer and Rhinestone is the place to get it in Portland!
Portland in the News: Invasive Hornets, PSU Dog Park, Sauna City & More | May 21, 2026
Oregon’s economy is heating up as sauna businesses pop up all over the state.
Win Tickets ($80): True West Presents ROSTAM – American Stories Tour @ Aladdin Theater | Indie Rock, Jazz
Rostam is a GRAMMY® Award-winning songwriter, producer, and composer.
Honey Tasting Flight in Carlton, OR @ Abbey Road Farm | Taste A Range of Honey, Wine, Cheese
Join us for a guided tasting of a spread of distinct honeys, each a reflection of the unique landscapes and blooms that surround us and other parts of the world.
Free Portland Trivia w/ Bridgetown Trivia | Sundays-Thursdays, Prizes
Bridgetown Trivia is your neighborhood pub trivia game done right.
Energy Trust of Oregon’s Salem Regional Presentation and Networking Event @ Family YMCA of Marion and Polk Counties | FREE Luncheon
Energy Trust invites you to a free luncheon to hear about case studies, new research and energy-savings approaches for local projects.
Debut of Triviology @ The Snug | Tacos, Cheap Drinks, Pinball
There’s a new venue in the Triviology lineup: The Snug!
Win Tickets ($70): Natalie Cuomo @ Mission Theater | New York Comedy Festival’s ‘Comics to Watch’
Based in New York, where she started comedy, Natalie Cuomo is an international touring stand-up comedian whose debut album ’Shut Up You Loved It’ released at #1 on the iTunes Comedy Charts.
Win Tickets ($80): McMenamins 4th Annual Grand Lodge Brewfest & Beyond in Forest Grove, OR | 35+ Taps Beer & Cider + Wine, Cocktails & NA Options,
More of a megafest than a brewfest, McMenamins 4th Annual Grand Lodge Brewfest & Beyond is a massive celebration of all things brewed, distilled, fermented, and tasty.
Sunday Night Splash @ Club Privata | PNW’s Premier Lifestyle Club
Members are encouraged to wear their poolside attire and red, white & blue!
Win Tickets ($12): Club Curfew: The 80s @ Crystal Ballroom | A Happy Hour Dance Party
Join us for a monthly Happy Hour dance party with DJ Gregarious where your night and your weekend starts EARLY!
2026 Portland Rose Festival Opening Night Fireworks @ Tom McCall Waterfront Park | Best Places to Watch, Photos, Video, Schedule
Rose Festival returns this weekend and that means fireworks on the Friday of Memorial Day Weekend! See below for the best places to view the show. ————- Related Portland Events & Info Events: Our May Events Calendar & Giveaways May 22: Fireworks River Cruise Memorial Day Weekend @ Island Style Charters | 7:30PM, 3 Hour Tiki…
Win Tickets ($50): Rhododendron w/ Sea Moss @ Aladdin Theater | Indie Rock
Transformation, growth, and rebirth drive Ascent Effort, the latest release from Portland, Oregon trio Rhododendron.
BACKFENCE Next Level Storytelling @ Powell’s City of Books | Live Storytelling
Just like the BACKFENCE Mainstage shows of yore, the storytellers for this show went through an intensive month-long process to explode the energy of their stories onto the stage.
Portland in the News: ‘Wildwood’ Film, Fire Buzzer Beater, Oregon’s ‘Moon Country’ & More | May 14, 2026
Long before Artemis II’s journey back to the moon, Apollo astronauts trained on Oregon’s lava fields, which scientists thought may mimic the surface of the moon.
Win Tickets ($68): Sleepytime Gorilla Museum w/ Gumby’s Junk @ Aladdin Theater | Experimental Rock
Perhaps we can call them Avant-Prog Metal, or Grindcore Funk Theater, or in the words of one particularly rapt concertgoer “Satanic Anarchic Viking Shit.”
Win 2 Tickets ($30): Danger Kitty w/ Purusa & Ashleigh Flynn @ Kelly’s Olympian | Indie Rock, Americana, Funk
Danger Kitty is a Northern California band making their first trip up to Portland on May 21 for a show at Kelly’s Olympian with Ashleigh Flynn and Purusa.
Win Tickets ($22): Decadent 80s @ 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!
Win Tickets ($70): Veganizer Asian Market @ The Redd on Salmon | Indoor/Outdoor Market, Lion Dancers, Chef Demos & More
Eat, drink, and shop your way through Portland’s (and Oregon’s) largest plant-based Asian heritage event!
2026 Portland Rose Festival Fireworks Dinner Cruises | Sunset Cruises w/ Plated Dinner
Enjoy a sunset dinner cruise featuring a delicious three-course meal, live piano music and access to our outdoor decks for narrated sightseeing.
Circus Royale Drag & Burlesque Extravaganza @ Echo Theater Company | Circus-Inspired Drag & Burlesque Showcase
RAE present this Circus Inspired Drag & Burlesque Showcase, featuring some of your Favorite Local Drag and Burlesque Artists!
Win Tickets ($30): The Future of Film is Female at PAM CUT @ The Whitsell | ‘Dreams in Nightmares’ + ‘Puddysticks’
The Future of Film is Female brings two of their recent indie femme-forward films to PAM CUT @ The Whitsell this weekend!
90s MTV Party @ Club Privata | PNW’s Premier Lifestyle Club
Bring out your bougie in a nod to the ’90s MTV VJs and Superstars that put corsets, bras, and midriffs as part of the fashion forward lifestyle!
Drag Brunch @ The Pharmacy | Hosted By Devlin Lynn Phoenixx
Devlin Lynn Phoenixx is back and she’s serving! Drag Brunch at The Pharmacy returns — and this time, we’re making it a whole situation.
A Portland-Made Documentary Debut: Grassroots to the Grid @ The Redd on Salmon | Free Community Resource Fair + Food Vendors + Film Q&A
What does climate justice look like in Portland?
May Events @ Columbia River Maritime Museum in Astoria OR | Historic Vessels Tour, Lectures, Museum Tour & More
Step into maritime history with guided tours, hands-on activities, and engaging lectures this month!
MANY Portland July 4th Weekend Events & Giveaways ($2,400+): Festivals, Fireworks, Concerts, Comedy, Theater, Film, & More!
| Weekend
Old Town Dance – Daniel Girón @ Darcelle XV | Community Dance Class Run by Daniel Girón
| All Ages, Dance, NW Portland
Portland New Generations Rotary Club Presents Roses and Rosé @ Portland International Rose Test Garden | Sip, Stroll & Support at Roses & Rosé 2026!
| Food & Drink, SW Portland
Rose City Vintage Expo @ Portland Expo Center | Antiques, Collectibles, Americana and More
| north portland, Shopping
Portland in the News: Doggo Dates, World’s Best Cheddar, Godzilla & More | July 2, 2026
| News
Shoestring Circus @ Hazel Dell Commons in Vancouver | Intimate, Story-Driven Circus Experience
| All Ages, theater
10% off Through July 6th – The 26th Annual Portland Erotic Ball @ Crystal Ballroom | 21+, Hosted by Sasha Scarlett, Live Music, Burlesque, Costume Contest, & More
| Dance, downtown, music, theater
THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!
| Today
New Portland Jobs: APANO Action Fund, Play On Shakespeare, World Forestry Center & More
| Jobs
Win Tickets ($358): HAREFEST @ Clackamas County Fairgrounds & Event Center | The Mother of All Tribute Festivals
| music
Win Tickets (30): McMenamins Presents Soul On the Floor with DJ CUTZ1 @ Lola’s Room | Funk, Soul, & R&B
| downtown
Win Tickets ($48): McMenamins Presents Taylor Bickett @ Mission Theater | Indie Pop
| All Ages, music, NW Portland
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