A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
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?
The Dinner Detective in Downtown Portland | Largest Murder Mystery Dinner Show In The U.S.
The Dinner Detective is an interactive murder mystery dinner experience.
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!
Tits & Giggles @ Curious Comedy | A Drag & Comedy Show
Laughs PDX presents this Hilarious and Fun Drag & Comedy Showcase, featuring some of your Favorite Local Comedians and Drag Performers!
Win Tickets ($36): The General (1926) Silent Film w/ Live Music By: MLTZR @ Mission Theater | Silent Film Classic w/ Live Music
A silent film experience featuring a silent film classic paired with live music.
Portland in the News: Farmers Market w/ Chefs, Musical Street Corners, Goodbye Lloyd Center & More | May 7, 2026
What would two lauded chefs do with $100 at PSU’s Farmers Market? The Willamette Week followed Gado Gado’s owners while they shopped for a picnic this past weekend.
2026 Mother’s Day Brunch @ The EastBurn | Mimosas, Food Specials
The EastBurn Public House is serving up mimosas, bloody marys, eggs benedict, scrambles, hash & more for Mother’s Day — No reservations needed.
Win Tickets ($240): 2026 Portland Rose Festival | Fireworks, CityFair, Fun Runs, Parades & More
The Portland Rose Festival has inspired the public to gather and celebrate against a backdrop of historic external forces for 119 years, demonstrating how our community can carry on traditions and celebrate unity.
Wine Wednesdays @ Negociant | Wine Flights + Flowers Mother’s Day Weekend
This Mother’s Day weekend we’re partnering with Toadstool Flowers by Wesley Younie to bring a little color to the shop.
Grape Culture @ PAM CUT Tomorrow Theater | Tragic Comedy w/ Toni Nagy and Seraphina Supernova
Grape Culture, created by comedian Toni Nagy and performance artist Seraphina Supernova, is a two-woman tragic-comedy stripping back the cultural bondage of domination without consent that upholds our current collective paradigm.
Portland Sage Singers presents ‘Rearview Mirror’ @ Patricia Reser Center for the Arts in Beaverton OR | Songs From Decades Gone By
The Portland Sage Singers are gearing up for our third concert titled “Rearview Mirror,” which will be performed June 2 & June 3, 2026 at the Patricia Reser Center for the Arts.
2026 Memorial Day Weekend Wine & BBQ @ Hip Chicks Do Wine | To-Go Sangria, Wine Tasting, Discounts
Kick off your Memorial Day Weekend with a deliciously fun and flavorful event at Hip Chicks Do Wine!
MANY Portland Weekend Events & Giveaways ($2,400+): Festivals, Concerts, Comedy, Theater, Film, & More!
| Weekend
Portland in the News: Waterfront Restaurant, Airport Accolades, Heatwave & More | June 11, 2026
| News
McMinnville Art Festival @ Downtown McMinnville | 50+ Artists & Artisans, Interactive Kids’ Crafting, Art Demos, & More
| All Ages, events, Free, Shopping, Visual Art
PRIDE at the Museum @ OMSI | A night at the museum celebrating the LGBTQ+ Community
| All Ages, events, Food & Drink, LGBTQ, Science, Shopping
Villain Arts Tattoo Festival @ The Rose Quarter | Celebrate the Art of Tattooing
| All Ages, events, Services, Shopping
New Portland Jobs: Portland Fire, Clark County Fair, Bend Chamber of Commerce & More
| Jobs
Win Tickets ($92): McMenamins Presents Justin Nozuka @ Mission Theater | Folk, Rock + R&B
| All Ages, music
7 Wonders of the Gorge @ Portland Spirit | Jet Boat Cruise, Majestic Views
| All Ages
Bigfoot Adventure Cruises @ Portland Spirit | Learn the History of Bigfoot on a Jetboat
| All Ages
Win Tickets ($72): Volunteer With SOLVE and Win Portland Pickles Tickets | Clean and restore neighborhoods and natural areas
| All Ages, Free
Watch 2026 World Cup Games @ Sticky Wicket | 7 TVs, 16 Taps, POG Shots
| events, north portland, sports
Win Tickets ($46): McMenamins presents Holi Summer Fest: A Celebration of Color @ Grand Lodge in Forest Grove, OR | Organic Colors, Bollywood & Bhangra Dance Party
| Dance, music
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