A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!
A Tim Curry & Tim Burton Inspired Drag & Burlesque Show + All Ages Spooktacular @ Echo Theater Company | Costume Contest, Trick or Treat & More
“Worlds Will Collide” as we fused two Cult Classic Icons into a Spooky and Fun Drag & Burlesque Experience!
Dreamcatcher @ 21ten Theatre in SE Portland | Improvised Theatre Inspired by You
Often, we ruminate on our dreams. What could they mean? How or why did I create that?
2025 Cinema of Horrors Haunted House in Kelso, WA | Four Immersive Haunted Houses
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.
2025 Spirit of Halloweentown in St. Helens | Haunted Attractions, Great Pumpkin Lightings, Celebrity Appearances, Kid Costume Contests, Family Fun & More!
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!
2025 Local 14 Art Show @ World Forestry Center | Featuring High Quality Original Art
LOCAL 14 is a not-for-profit group whose mission is to support Northwest women and men in the arts and provide scholarships to deserving art students.
Win Tickets ($30): Left on Tenth w/ Mr. Vale’s Math Class @ The Goodfoot | Funk, Rock, Reggae
Left on Tenth is group of friends who started playing music together on 10th Ave. in Bozeman, MT in 2016. They share a passion for live performance and fun.
Bowser’s Boo Bash @ Zenith Vineyard in Salem | Dog & Human Costumes, Buffet & Brews, Oregon Humane Society Fundraiser
Join Oregon Humane Society for the return of Bowser’s Boo Bash!
Win Tickets ($60): Maris + Caroline Kingsbury @ Mission Theater | Queer Power Pop
Caroline Kingsbury and Maris present an ‘Intergalactic Sapphic Pop Show’ hitting the road in the US and Canada this fall!
Portland in the News: NYT Food Accolades, Winter Weather Predictions, Fall Day Trips & More | September 11, 2025
Do you feel that slight chill in the air? Fall is on the way and Portland Monthly has some day trip ideas to take advantage of the season.
Wine Wednesdays @ Négociant | Weekly Wine Flights & Tastings
Wine Wednesday is now in its third year and has become a staple in our weekly routine and part of the tradition around here
Electrify Portland! Home Electrification Fair @ The Redd on Salmon | Shop Energy Efficient Home Upgrades
Get ready to make your home healthier, more comfy, and resilient! Join us for Electrify Portland! on Saturday, September 27th from 11am to 3pm, hosted at the beautiful Redd on Salmon Street.
2025 Belmont Street Fair | FREE, Local Makers, Live Music, Kids Fun Zone & More
Get ready for one of Portland’s biggest block parties — the Belmont Street Fair is back!
2025 Portland Oktoberfest @ McMenamins: Edgefield, Kennedy School, Crystal Hotel, Cornelius Pass Roadhouse | Beer & Cider, Live Music, German Food, Plant Sale, Golf Tourney, & More
Portland Oktoberfest means celebration and beer – so McMenamins is serving up tasty German-style specials, plenty of beer and live music as a backdrop to it all.
Win Tickets ($56): Pat Burtscher @ Mission Theater | Canadian Comedian
Pat Burtscher was born in Austria via a Greek woman raised in Canada and is currently based in NYC where he’s a regular at The Comedy Cellar and other cool places.
2025 Portland Weird Fest @ Oaks Park | Chicken Beauty Contest, 50+ Weird Vendors, Live Performances
Presented by Weird Portland United, Weird Fest is the ultimate celebration of all things quirky, colorful, and delightfully unexpected.
Quad Inc. 50th Anniversary Gala @ OMSI’s Theory Room | 70s-Themed, Food & Drink, Auction
Quadriplegics United Against Dependency, Inc. (Quad) is a Portland-based 501c3 organization dedicated to advancing the rights and independence of adults living with physical disabilities through the provision of barrier-free, low-cost housing and 24/7 supportive services.
Win Tickets ($26): TROPITAAL! w/ DJ Anjali and The Incredible Kid @ The Goodfoot | Desi Latine Soundclash
A Desi/Latine Soundclash where the hottest club sounds from India and Latin America go head to head in an all-night dance-off of epic proportions
2025 Weinfest @ Abbey Road Farm | German Wines, Food, Music
Raise a glass and join us for Weinfest on Sunday, September 22, a celebration of German wines, cuisine, and culture right here in wine country.
Afternoon Garden Tea @ Victorian Belle | Sweet & Savory Treats
The Victorian Belle’s Afternoon Garden Teas are a fun and elegant way to celebrate in September!
The Dinner Detective in Downtown Portland | Largest Murder Mystery Dinner Show In The U.S.
Are you tired of the same old date nights? Portland’s perfect remedy for entertainment boredom is The Dinner Detective.
Win Tickets ($80): Jason D. Williams w/ Supersuckers, Wayne Hancock @ Mission Theater | Country & Rock Pianist
A wild man of the keys and a rockabilly legend in his own right, Jason D. Williams has lived more musical lives than most.
Win Tickets ($49): Will Paquin @ Mission Theater | Indie Rock
Will Paquin used to write in isolation – songs came together behind closed doors, in bedrooms, dorm rooms, backseats.
Win Tickets ($57): Little Hurricane @ Mission Theater | Blues-Rock
Little Hurricane formed in 2010 when Anthony “Tone” Catalano decided to start a band after years of working in studios as a recording engineer for Gwen Stefani, Neil Young and many others.
September Albariza Wine Bar @ Proletariat Butchery | Wood Fired Venison Steaks, Cheese, Caviar
Join Proletariat Butchery the 2nd FRIDAY of every month for Albariza Wine Bar! $45 gets you all the tapas from our butcher block and glasses of really good wine are $15/gls, with $25/gls fancy pours.
Cirque la Nuit – Zodiac Night @ Club Privata | PNW’s Premier Lifestyle Club
Fantasy takes center stage and the big top becomes your playground of pleasure.
Fall Fun @ Frog Pond Farm | Llama Corn Maze, Pumpkin Patch, Food & Drink
Frog Pond Farm’s Pumpkin Patch opens September 19—meet llamas in the patch, explore the llama-themed corn maze, bounce through the giant Bounce Park, and visit 80+ animals.
2025 Portland Erotic Ball @ Crystal Ballroom | Premier Adult Halloween Party
Remember YOU are the PARTY, so DRESS to THRILL for 3 levels of non-stop entertainment, eye candy and spectacle in this all-lifestyles-are-welcome event that helped birth Portland’s motto “Keep Portland Weird!”
Grand Kyiv Ballet presents Tchaikovsky’s Swan Lake | A Drama of Love and Betrayal
Grand Kyiv Ballet invites you to experience one of the greatest masterpieces of world art — Pyotr Ilyich Tchaikovsky’s Swan Lake.
2025 Spirit of Halloweentown Cruises on the Portland Spirit | The Ghostly Voyage Cruise, Explore Famous Halloween-Themed Town, Costumes
Embark on a spooky voyage to the famous Spirit of Halloweentown in St. Helens!
Portland in the News: Missing Swifts, York Bust to Return, Giant Spiders & More | September 4, 2025
Every September, Portlanders gather to watch the Vaux’s Swifts put on an aerial show at Chapman Elementary. But it appears the birds have declined to perform there so far this year.
Win Tickets ($70): 2025 Portland Coffee Festival @ The Redd on Salmon Street | Tastings, Demos, Food, Whiskey
Explore a bustling hall at the Redd on Salmon filled with local roasters, coffee artisan and specialty vendors — all ready to share their passion, products and stories.
2025 Annual Dahlia Festival @ Swan Island Dahlias | Fresh Cut Flowers, Music, Food Carts
Don’t Miss the Dazzling Dahlias in bloom August through September for the Annual Dahlia Festival at Swan Island Dahlias.
2025 Clinton Street Fair | FREE, Vendors, Bike Bus, Skateboarding Demos, International Foods, & More
Ride in with the Abernethy Bike Bus, explore hundreds of vendors, brick and mortar businesses and savor international foods.
Wine & Game Day Snacks @ Hip Chicks Do Wine | 6 Wines Paired w/ Game Day Snacks
Whether you’re gearing up for the big game or simply love a good wine and snack pairing, this event is for you!
CANCELLED: Arlie w/ Nordista Freeze @ Mission Theater | Indie Pop
Arlie is a band created by singer-songwriter, composer & multi-instrumentalist Nathaniel Banks
Win Tickets ($30): Lady Hill Fall Sheepdog Classic @ Lady Hill Winery | Dog Show, Kids Activities, Food & Wine
Celebrate the season at the Lady Hill Fall Sheepdog Classic, a three-day event that combines the excitement of traditional sheepdog trials with the rustic beauty of Oregon wine country.
THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!
| Today
2026 Swan Island Dahlia Festival | 50 Acres of Blooms, Food Carts, Live Music
| All Ages, events, Food & Drink, music
7 Deadly Sins Pants On Fire Family Friendly Show @ White Eagle Saloon | Seven True Tales, One Lie
| All Ages, Comedy, north portland, theater
Win Tickets ($130): Portland Weird Fest @ Oaks Park | 60+ Vendors, Rides, Live Bands, Costume Contest & More
| All Ages, Food & Drink, music, SE Portland, Shopping
Win Tickets ($136): Dogstar w/ The Backfires @ Crystal Ballroom | Keanu Reeves, Alt-Rock
| All Ages, downtown, events, music
Win Tickets ($92): Marc Price @ Mission Theater | Comedy, Star of ‘Trick or Treat’, ‘Family Ties’
| Comedy, NW Portland
Win Tickets ($22): Decadent 80s w/ DJ NoN @ Crystal Ballroom | Portland’s Longest Running 80s Night
| downtown, events, music
2026 Cannon Beach Cottage Tour | Self-Guided Walking Tour of Beautiful Homes, Opening Night Bash
| All Ages, events, Visual Art
2026 Time-Based Art Festival @ Portland Institute for Contemporary Art | Experimental Performances, Live Music, Dance & More
| Dance, events, Film, Food & Drink, music, NE Portland, theater, Visual Art
Lake Oswego Clean Energy and EV Fair @ Lake Oswego United Methodist Church | Test Drive EVs, Learn About Solar, Batteries & More
| All Ages, events, Home Show, Services, Shopping
Win Tickets ($42): Valkerie w/ Withholden, Laughing About Nothing, Fawkes Glove @ Mission Theater | Alternative Rock
| All Ages, music, NW Portland
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