A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
Conquer the Canyon @ Dry Canyon Trail in Redmond, OR | 5K, 10K, Doggies Dash, Natural Views
Get ready to Conquer the Canyon! Join us Saturday, June 6, 2026, in Redmond, Oregon for one of Central Oregon’s most scenic race experiences.
2026 River Cruises @ Island Style Charters | Tiki Night, Sunset Cruises, City Lights & More
Experience Portland like never before aboard Island Style Charters! From Happy Hour to Family Fun, there’s a cruise for everyone!
Unicorn Beach Party @ Club Privata | PNW’s Premier Lifestyle Club
Let the sun shine down and enjoy a Unicorn night at Club Privata.
2026 Downtown Portland Free Summer Concerts: Noon Tunes @ Pioneer Courthouse Square
It’s not summer in Portland without FREE lunchtime concert series! The Noon Tunes Summer Concert Series returns to Pioneer Square on Tuesdays and Thursdays June 2 – July 30!
Win Tickets ($70): Elijah Scott – In A Bar Somewhere Tour @ Mission Theater | Country-Americana
Elijah Scott is a country-Americana singer-songwriter from Banning, California whose distinctive voice and hybrid sound blend heartfelt storytelling with urban rhythm and soul.
2026 Portland Original Practice Shakespeare Festival in Parks | Free, Audience Interaction, Onstage Prompter
OPSFest brings no-cost Shakespeare to parks all over the Portland Metro area. The company uses the original practice techniques of Elizabethan England: limited rehearsal, scrolls in hand, audience interaction, and an onstage prompter! ——————— Related Portland Events & Info Giveaways: Win Portland STUFF: Prizes, Concert Tickets, Comedy, Festivals, Gift Cards, Food & Drink World Cup:…
Portland in the News: Burnside Centennial, Wish Tree, Bloom Tour & More | May 28, 2026
A chestnut tree in NE Portland has held wishes from strangers for the past ten years.
Win Tickets ($60) Made with Pride Wine Festival @ Directors Park | Community, Creativity, and Wine
Celebrate community, creativity, and incredible wine at the Made with Pride Wine Fest—a vibrant afternoon dedicated to showcasing queer-owned wineries from across Oregon.
Meow Village Presents Arts, Crafts, and Cats @ Multnomah Arts Center | Market, Local Arts & Goods, Food, Cats & Kittens!
Join us for a heartwarming day filled with creativity, compassion, and cats!
Backcourt Collective Presents Portland Fire Pre-Game Party @ Cartside / The Garden Tavern | Food, Fun, and Raffle
Pre-game with us on Saturday before tip-off between Portland Fire and the Indiana Fever at Moda.
LES Shakespeare Company presents The Words Will Come: Inside the Dyslexic Mind @ Shaking The Tree Theatre | Projection, Immersive Sound, Physical Storytelling
An Iranian-American woman confronts her younger self — a child trapped in a world where letters refuse to behave.
Farm to Plate Dinners @ Topaz Farm | Hyper-Seasonal Food, Drinks
Join us beneath our 500-year-old oak tree for a multi-course, family-style dinner shaped entirely by what’s growing on the farm that week.
Win Ticket ($90): Portland Fire vs Connecticut Sun @ Moda Center | Amazing View, Get Autographs, Section 102
Experience the excitement of WNBA in Portland as the Portland Fire face off against the Connecticut Sun.
Blueprint Choirs Presents Music Festival and Gala @ Lloyd Center | Entertainment, Fun, & Food
Come and join Blueprint (and all our numerous symphonies and choirs) for a day of entertainment, fun, and food!
Win Tickets ($260) Portland Horror Film Festival @ Hollywood Theater & Clinton Street Theater | 60+ International Short & Feature Films
Portland Horror Film Festival returns to the historic Hollywood Theatre and Clinton Street Theater June 3-7th for its 11th annual event!
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!
MANY Weekend Events & Giveaways ($2,400+): Halloween, Festivals, Concerts, Comedy, Theater, Film, & More!
| Weekend
Nocino Liqueur Release Party @ New Deal Distillery | Fall Cocktail Menu, Behind-The-Scenes, Take Home This Year’s Batch
| events, Food & Drink, Free, SE Portland
The Nitemare B4 Xmas w/ The Saloon Ensemble @ Alberta Rose Theatre | Sing-A-Longs, Costume Contest, Screaming Contest
| All Ages, events, Halloween, music, NE Portland, theater
George Martin: The Beatles Scores and More @ Hallowed Halls | Rare Film, Audio & Stories of George, the Beatles, Abbey Road
| All Ages, events, Film, Lectures, music, SE Portland
Stumptown Stages presents ‘Annie’ @ Dolores Winningstad Theatre | Tony Award-Winning Musical
| All Ages, downtown, SW Portland, theater
Distinguished and Disney @ Blueprint Arts Ensemble | Music from Aladdin, Frozen, Mulan & More
| All Ages, events, music, NE Portland
Circus Soiree @ A-WOL Dance Collective | Immersive Dance Experience
| All Ages, Dance, NE Portland
Win Tickets ($92): 2000s New Years Eve Y2K Ball @ Crystal Ballroom | Two Floor Massive Dance Party
| Dance, downtown, events, music
New Portland Jobs: Stumptown Coffee, Friends of Trees, Meals On Wheels People & More
| Jobs
Win Tickets ($124): 94/7FM KNRK presents “December to Remember” w/ Dirty Heads @ Crystal Ballroom | Reggae Rock
| All Ages, downtown, events, music
Win Tickets ($38): Apes of the State w/ Pigeon Pit @ Mission Theater | Folk, Punk
| All Ages, events, music, NW Portland
The Rise of Houdini @ Experience Theatre Project | An Effervescent Burlesque & Séance to Raise the Great Houdini
| events, Food & Drink, Halloween, theater
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