A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!
2026 Spirit of Halloweentown in St. Helens, OR | Oregon’s Must-Visit Halloween Festival
September 26 -October 31 – Welcome to Spirit of Halloweentown where the magic of the season transforms the historic riverfront town of St. Helens, Oregon into a one-of-a-kind Halloween destination!
The Crystal Gems in the Land of Ooo! @ Echo Theater Company | Drag, Burlesque, Costume Contest
September 18 – Come along with us to the worlds of both Adventure Time and Steven Universe in The Trash People from the Dump & Rogue Apostles Entertainment presents The Crystal Gems in the Land of Ooo!
Win Tickets ($42): Bobby Weir’s Bday Celebration w/ Family Mystic @ White Eagle Saloon | Funk, Soul, Psych Rock, Americana
October 17 – Family Mystic is a rising force in the west coast music scene led by rich four-part vocal harmonies & ecstatic grooves.
Win Tickets ($110): Kruder & Dorfmeister ‘K&D Kicks 30 Anniversary Tour’ @ Crystal Ballroom | Down Tempo, Trip Hop, Nu Jazz
September 27 – Kruder & Dorfmeister’s story is not just a story of refusal and renunciation.
New Portland Jobs: Rose Haven, Impact NW, Harbor Circles & More
New Portland Jobs: Rose Haven, Impact NW, Harbor Circles & More!
Radical Harvest Craft Faire & Community Center @ SymbiOp Garden Shop | Clothing/Craft Supply Swap, 40+ Local Makers, Giveaways
October 3-4 – This free and family-friendly event features 40+ local makers and artists vending a huge variety of handmade goods.
Stumptown Stages presents Guys & Dolls @ Winningstad Theatre | Tony Award-Winning Musical
October 2-25 – Stumptown Stages begins its 2026-27 Musical Season with the uproariously funny GUYS & DOLLS!
Happy Girls Sisters Half Marathon @ Five Pine Lodge in Sisters, OR | 10K & 5K in the Deschutes National Forest
October 24 – The Happy Girls Sisters Half Marathon, 10K & 5K returns Saturday, October 24, 2026, bringing together women of all ages and abilities for a day of running, connection and Central Oregon scenery.
Brews Cruise @ Portland Spirit | Local Breweries, Cideries & Distilleries
October 1 & 22 – Taste your way through some of the best Pacific Northwest craft beverages aboard the Portland Spirit!
Win Tickets ($74): Floater @ Crystal Ballroom | Alternative Rock
October 30 – With intense and unforgettable live performances, their fan base has grown over the years to a fever pitch and Floater fans are legendary for their dedication.
Community Energy Project presents ‘Grassroots to the Grid’ @ Mission Theater | Locally Produced Clean Energy Documentary
September 23 – Join Community Energy Project for a screening of Grassroots to the Grid, a locally produced documentary exploring Oregon’s clean energy transition.
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.
Local 14 Art Show & Sale @ World Forestry Center | Painting, Sculpture, Jewelry, Fiber Arts & More
October 2-4 – Featuring a juried selection of PNW artists working in a wide array of mediums: painting, sculpture, fiber arts, jewelry, and more!
Heartbeat Silent Disco presents Mystery Ship Masquerade Party @ Portland Spirit | Silent Disco, Food & Drinks
October 10 – Join us on the 10th of October from 10:00 PM to 1:00 AM for a night of enchantment and intrigue as we embark on an unforgettable journey aboard The Portland Spirit.
Portland in the News: Happy Birthday MAX, Swifts Relocate, Big Spiders & More | September 10, 2026
It’s Virgo season, and the MAX train is celebrating its 40th birthday. The first MAX train took its inaugural ride on September 5, 1986.
Wicked Craft: Mabon Market @ Rae Loft | FREE, Artisan Vendors, Pagan Harvest Festival
September 19 – Mabon is a Pagan harvest festival celebrating the autumn equinox, typically in late September, and represents the second harvest of the year as well as the balance between light and dark.
2026 ADX Fest | 50 Collaborators Across 60+ Events, Workshops, BodyVox’s Creepy Cupcakes & More
October 2-31 – PDX Pipeline readers are invited to Xperience the first ADX Fest, a region-wide celebration of Art, Design, and the Xchange between hundreds of creatives across disciplines.
Oregon Pride in Business Rainbow Expo @ Social Good Place | LGBTQIA2S+ Marketplace, Bites & Beverages, Community Resource Hall
September 26 – We’re excited and proud to host our First Annual Rainbow Expo presented by Peak Promo, a free community celebration spotlighting queer-owned businesses!
Fur Baby Love Fest @ Meldrum Bar Park in Gladstone | 60+ Vendors, River Walk, Doggy Dance Party, Costume Contest & More
September 13 – Join us for the Fur Baby Love Fest RiverWalk and help support Oregon Dog Rescue.
Win Tickets ($92): Marc Price @ Mission Theater | Comedy, Star of ‘Trick or Treat’, ‘Family Ties’
September 21 – Marc, best known as Skippy from the beloved 80’s sitcom Family Ties, is a multi-talented performer who has conquered the worlds of stand-up comedy, acting, hosting, and even writing and producing.
Pumpkin Spice and Everything Nice…With Wine @ Hip Chicks Do Wine | Wine Flight, Pumpkin Spice Sangria, Autumn Appetizers
September 18-20 – Join us at Hip Chicks do Wine for a deliciously cozy weekend filled with fall flavors, fabulous wine, and plenty of pumpkin spice.
Win Tickets ($42): Valkerie w/ Withholden, Laughing About Nothing, Fawkes Glove @ Mission Theater | Alternative Rock
September 25 – In their second project, Myocardia, we meet the alternative rock four piece, Valkerie, after accumulated break ups, heart conditions, and deaths.
Agatha Christie’s ‘And Then There Were None’ @ Experience Theatre Project | Immersive Production of a Classic Mystery
September 17 – October 18 – Adapted from Agatha Christie’s classic mystery, this immersive production brings the psychological tension of the classic tale into immediate, breath-held proximity.
Win Tickets ($70): Patrick Wolf @ Mission Theater | Baroque, Electronic, Pop
October 31 – Patrick Wolf released his first E.P. at the age of 19, a groundbreaking debut of classical, folk, and electronic music that set the pace for a stellar decade.
Pride & Prejudice @ Portland Center Stage | A Bold New Comedic Take on a Beloved Classic
September 27 – October 25 – From the playwright behind 2019’s Sense & Sensibility and 2023’s Ms. Holmes & Ms. Watson – Apt. 2B comes a bold new comedic take on a beloved classic.
Win Tickets ($250): Circle V Portland @ Castaway | Unforgettable Plant-Based Tasting Experience, Fundraiser
September 20 – Join us on Sunday, September 20 at Castaway for a one-of-a-kind walkaround tasting experience featuring creative and oftentimes unexpected chef collaborations, tasty bites from craft food makers, and sips from a dozen beverage producers.
Win Tickets ($56): Constant Debauchery w/ Kiss Me Kiss Me Kiss Me, West End Entertainment District @ Mission Theater | Depeche Mode Tribute, Cure Tribute
October 2 – Constant Debauchery is the Pacific Northwest’s premier Depeche Mode celebration band.
Win Tickets ($116) McMenamins Presents Everclear – Lucky 7 Tour w/ American Hi-Fi @Crystal Ballroom | Alternative Rock
Everclear is hitting the road again this fall with The Lucky 7 Tour!
Shanrocks Triviology @ Thunderbird Mississippi | Patio, Quality Food & Drinks
Thursdays – We’re having such a great time at Thunderbird on Foster that we’re taking trivia to North Portland!
Drag Brunch @ The Pharmacy | Hosted by Devlin Lynn Phoenixx
September 20 – A 21+ drag brunch in the heart of Northwest! Doors at 11:00 am with show at 12 pm. $35.00 gets you a fabulous meal and your first mimosa!
Win Tickets ($48): McMenamins Presents Taylor Bickett @ Mission Theater | Indie Pop
November 1 – Taylor Bickett is a storyteller at heart.
Win Tickets ($40): Forest Pub – Play (Art X Ecology X Design) @ McMenamins Mission Theater | Exploring Creative Approaches to Environmental Storytelling.
September 14 – Can art and design change the way we understand forest management?
Win Tickets ($92): McMenamins Presents Justin Nozuka @ Mission Theater | Folk, Rock + R&B
October 20 – Justin Nozuka is a singer-songwriter and producer born in Queens, New York and raised in Toronto, Canada.
The 26th Annual Portland Erotic Ball @ Crystal Ballroom | 21+, Hosted by Sasha Scarlett, Live Music, Burlesque, Costume Contest, & More
October 31 – Portland Erotic Ball, one of the city’s most iconic and enduring Halloween traditions, returns for its 26th anniversary this fall with a bold new vision while continuing its legacy as Portland’s largest adult Halloween event.
Win Tickets ($60): Great Lake Swimmers’ Caught Light Tour 2026 @ Mission Theater | Indie-Folk
October 30 – Featuring a blend of acoustic instruments, rural soundscapes, and wistful vocals, Great Lake Swimmers are a critically acclaimed indie-folk group led by Tony Dekker.
Plant Bingo @ Hip Chicks Do Wine | Beautiful Plant Prizes, Wine, Snacks
September 11 – Get ready for a fabulous afternoon of wine, plants, and plenty of sass!
THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!
| Today
2026 Spirit of Halloweentown in St. Helens, OR | Oregon’s Must-Visit Halloween Festival
| events, Halloween
The Crystal Gems in the Land of Ooo! @ Echo Theater Company | Drag, Burlesque, Costume Contest
| events, LGBTQ, SE Portland
Win Tickets ($42): Bobby Weir’s Bday Celebration w/ Family Mystic @ White Eagle Saloon | Funk, Soul, Psych Rock, Americana
| events, music, north portland
Win Tickets ($110): Kruder & Dorfmeister ‘K&D Kicks 30 Anniversary Tour’ @ Crystal Ballroom | Down Tempo, Trip Hop, Nu Jazz
| downtown, events, music
New Portland Jobs: Rose Haven, Impact NW, Harbor Circles & More
| Jobs
Radical Harvest Craft Faire & Community Center @ SymbiOp Garden Shop | Clothing/Craft Supply Swap, 40+ Local Makers, Giveaways
| All Ages, events, Free, SE Portland, Services, Shopping
Stumptown Stages presents Guys & Dolls @ Winningstad Theatre | Tony Award-Winning Musical
| All Ages, downtown, theater
Happy Girls Sisters Half Marathon @ Five Pine Lodge in Sisters, OR | 10K & 5K in the Deschutes National Forest
| Active Lifestlye, All Ages, events
Brews Cruise @ Portland Spirit | Local Breweries, Cideries & Distilleries
| downtown, events, Food & Drink
Win Tickets ($74): Floater @ Crystal Ballroom | Alternative Rock
| All Ages, downtown, music
Community Energy Project presents ‘Grassroots to the Grid’ @ Mission Theater | Locally Produced Clean Energy Documentary
| All Ages, events, Film, Lectures, NW Portland
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