A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!
2026 Sitka Art Invitational Show & Sale @ Oregon Contemporary | 100 Local Artists, 300 Works of Art
October 16-18 – The Sitka Art Invitational show and sale—the Northwest’s largest and longest-running art event of it’s kind is happening October 16-18, 11am-5pm. Admission is free.
PDX Bar Coalition presents BARMAGEDDON | Cocktail Classes, Parties, Distillery Tours & More
October 4-7 – Barmageddon is a grassroots, DIY showcase of Portland’s bar scene taking place October 4-7, 2026.
Win Tickets ($116): 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 ($52): Haley Johnsen @ McMenamins Crystal Ballroom | Heart-Forward Alt-Pop
November 20- Haley Johnsen is a Portland-based Americana artist blending alt-pop edge with powerhouse vocals and emotionally charged songwriting.
Cinema of Horrors Drive-In Experience @ Clark County Fairgrounds | 19 Horror Thrillers, Monsters, Snack Bar
October 7-31 – A live-action, drive-in horror movie experience where monsters from the screen come to life.
Win Tickets ($110): Taste of Portland @ Castaway | Sample Bites from Nostrana, Tusk, Ava Genes & More
October 5 – Join us Monday, October 5, from 6–9 p.m. at Castaway Portland for an evening celebrating the restaurants that make this city special.
Win Tickets ($62): Dev Lemons – Eat the Pavement Tour @ Mission Theater | Alt-Pop, Bedroom Pop
November 18 – Equal parts alt-pop artist, songwriter, comedian, and internet personality, she has cultivated a fiercely loyal audience through her sharp wit, fearless authenticity, and genre-blurring music that balances vulnerability with humor.
Holiday Afternoon Tea @ Victorian Belle | Artisan Teas, Pastries, Savories
December 5-27 – The Victorian Belle’s Holiday Afternoon Tea is a fun and elegant way to celebrate the holidays!
Win Tickets ($66): 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: Lights Out for Birds, PDX Punk Candles, Preventing Food Waste & More | September 24, 2026
A Portland artist has created a line of prayer candles dedicated to Portland punk legends like Toody Cole, John ‘Elvis’ Schroder and Portlandia’s Jedediah Aaker.
Win Tickets ($42): Georgia Parker @ Mission Theater | Indie Folk, Chamber Pop, Indie Rock
November 3 – Georgia Parker is a singer-songwriter from Kent, England, now based in Los Angeles. She released her debut album, Same Time Tomorrow, in August 2024, establishing herself as a distinctive voice in contemporary folk and indie music.
Win Tickets ($22): Decadent 80s @ Crystal Ballroom | Portland’s Longest Running 80s Dance Night
November 27 – Get ready for a fun night of dancing to all your favorite hits and requests from the 1980s!
2026 Pumpkin Patch @ Frog Pond Farms in Wilsonville, OR | Llamas, Bounce House, Farm Animals & More
Through November 1 – Frog Pond Farm is a pumpkin patch like no other. On weekends, meet llamas in the pumpkin patch and try our one-of-a-kind llama obstacle course.
Portland Opera Presents ‘La Traviata’ in Concert @ Keller Auditorium | Giuseppe Verdi’s Masterpiece
November 6-7 – One of the most beloved operas ever composed, La Traviata combines sweeping emotion with some of the most recognizable music in the operatic repertoire.
Island Style Cruises Sips & Sights Tasting Cruise | Taste Local Wines, Snacks 2-Hour Scenic River Cruise
Sundays in October – Spend an afternoon sipping and cruising Portland on our Sips & Sights Tasting Cruise!
Win Tickets ($170): 2026 HP Lovecraft Film Festival @ Hollywood Theater | 50+ Short & Feature Films
October 2-4 – The 31st Annual H. P. Lovecraft Film Festival® kicks off Spooky Season Oct 2-4, 2026 on all 3 screens at the Hollywood Theatre!
Chrome Industries Warehouse Sale in NW Portland | Apparel, Messenger Bags, Slings & More
September 26-27 – Calling all Portland area Chromies, Chromeaholics, Chrome-enthusiast, and people lookin’ for a screamin’ deal.
New Portland Jobs: Leach Garden Friends, Alberta Co-op Grocery, Creo Chocolate & More
New Portland Jobs: Leach Garden Friends, Alberta Co-op Grocery, Creo Chocolate & More!
Watch NFL/Seahawks @ Casa Diablo | Seahawks Sundays On The Patio, Food & Drink Specials
Join Casa Diablo for Seahawks Sundays from 1PM on their sports patio.
Cinema of Horrors Haunted House @ Three Rivers Crossing in Kelso, WA | The Portland Area’s #1 Haunted Attraction
September 25-November 1 – Located at the Three Rivers Mall in Kelso, WA, this massive haunted event draws thrill-seekers from across Oregon and Washington, including visitors from Portland, Seattle, and St. Helens’ famous Halloweentown.
2026 Thrill The World Dance @ Irving Park | World Wide Thriller Dance, Halloween Event
The 2026 Portland Halloween season is here and Thrill The World Dance Practice start on September 26th at Irving Park’s basketball court. The 2026 Portland Thrill The World / Thriller Dance takes place on October 24 at 3PM!
Portland Playhouse presents Thurgood @ Adrienne C. Nelson High School in Happy Valley, OR | One Man’s Fight to Change the Country
September 24-27 – Before he became a Supreme Court Justice, Thurgood Marshall traveled the United States as a civil rights attorney, taking on cases that would reshape the nation.
Meeting of the Mentors @ Revolution Hall – Show Bar | Network with Oregon’s Design and Build Community
October 1 – It’s that time of the year again! Energy Trust of Oregon’s Meeting of the Mentors is back for its sixth consecutive year.
Kids Book Flash Sale @ Rose City Reads | $1 Books Including Young Adult
October 9-10 – It’s that time of the year again! Our biggest sale is back and better than ever!
Portland in the News: Chicken Beauty Contest, NYT’s Fave PDX Restaurant, Vegan Bites & More | September 17, 2026
Portland’s fanciest chickens will cluck and strut down the runway at Portland Weird Festival’s Chicken Beauty Contest this Saturday.
PEAKING: Psychedelics and the Pursuit of Happiness @ Cinema 21 | Portland Film Premiere, Live Q&A
September 24 – PEAKING takes viewers inside psychedelic therapy and healing, capturing rare, intimate experiences as they happen.
The Wedge @ Alder Block | Taste & Buy 100s of Cheeses, Specialty Foods, Beer, Wine & More
September 26 – The Wedge is Portland’s celebration of cheese and everything that goes with it, happening Saturday, September 26 from noon to 5pm at Alder Block, home of the Portland Night Market.
Kumoricon 2026 @ Oregon Convention Center | Anime & Japanese Culture Convention
Celebrating more than twenty years of anime and Japanese culture, Kumoricon is back for its biggest year yet!
19th Annual Oregon Music Hall of Fame (OMHOF) Induction & Concert @ Aladdin Theater | Live Auction, Performances by M. Ward, Steve Berlin (Los Lobos), Calobo
October 10 – The Concert will feature 3 performances by 3 or the nights inductees: Steve Berlin (Los Lobos), a reunion of 90’s acoustic-rock jam band Calobo and M. Ward.
2026 Spirit of Halloweentown Cruises on the Portland Spirit | The Ghostly Voyage Cruise, Explore Famous Halloween-Themed Town, Costumes
October 3 – November 1 – Embark on a spooky voyage aboard the Explorer Jetboat to the famous Spirit of Halloweentown in St. Helens!
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.
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!
THIS WEEK in Portland: Halloween Events, Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!
| Today
2026 Sitka Art Invitational Show & Sale @ Oregon Contemporary | 100 Local Artists, 300 Works of Art
| All Ages, events, Free, music, north portland, Visual Art
PDX Bar Coalition presents BARMAGEDDON | Cocktail Classes, Parties, Distillery Tours & More
| events, Food & Drink
Win Tickets ($116): Brews Cruise @ Portland Spirit | Local Breweries, Cideries & Distilleries
| downtown, events, Food & Drink
Win Tickets ($52): Haley Johnsen @ McMenamins Crystal Ballroom | Heart-Forward Alt-Pop
| All Ages, downtown, music
Cinema of Horrors Drive-In Experience @ Clark County Fairgrounds | 19 Horror Thrillers, Monsters, Snack Bar
| events, Film, Food & Drink, Halloween
Win Tickets ($110): Taste of Portland @ Castaway | Sample Bites from Nostrana, Tusk, Ava Genes & More
| events, Food & Drink, NW Portland
Win Tickets ($62): Dev Lemons – Eat the Pavement Tour @ Mission Theater | Alt-Pop, Bedroom Pop
| events, music, NW Portland
Holiday Afternoon Tea @ Victorian Belle | Artisan Teas, Pastries, Savories
| All Ages, events, Food & Drink, north portland
Win Tickets ($66): Heartbeat Silent Disco presents Mystery Ship Masquerade Party @ Portland Spirit | Silent Disco, Food & Drinks
| downtown, events, music
Portland in the News: Lights Out for Birds, PDX Punk Candles, Preventing Food Waste & More | September 24, 2026
| News
Win Tickets ($42): Georgia Parker @ Mission Theater | Indie Folk, Chamber Pop, Indie Rock
| All Ages, music, NW Portland
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