A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
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.
Mom Rave @ Rae Loft | Music, Vendors, Dancing
Yes we fu**ing can put on a party JUST FOR THE LADIES! Entirely produced, managed, and performed by bad ass boss babes! Let’s do the damn thing!
Win Tickets ($42): Sabertooth Presents Headspace Music Festival @ Crystal Ballroom | Psychedelic Rock Featuring Gata Galáctica, Fluid Druid, Salo Panto, Rarefaction
Headspace carries the spirit of Sabertooth Festival into a new era — showcasing Portland’s finest local bands in a haze of heavy riffs, swirling sounds, and psychedelic vibes.
Win Tickets ($56): Birdtalker w/ Boy Golden @ Mission Theater | Indie/Folk
Indie/folk group Birdtalker released today their new album All Means, No End through Tone Tree Music.
Win Tickets ($104): James @ Crystal Ballroom | Alternative Rock
With more than 25 million albums sold over a longstanding career, James are amongst the most commercially and artistically successful alternative rock bands of their era.
Win Tickets ($48): Campfire Tales @ Echo Theater | Live True Stories
Campfire Tales is a fresh take on live storytelling—a welcoming space where personal stories come to life.
Portland in the News: Tango in the Park, (North) West Coast Hip-Hop, Dino Exchange & More | August 28, 2025
It’s time to dust off your cha-cha heels. A recently installed parquet floor in Director’s Park invites Portlanders to dance the tango every other Monday night through September.
Wine & Design w/ Gifford Flowers @ Hip Chicks Do Wine | Fall Wreath Class
In this session of our Wine & Design series, instructor Laura Gifford Kerr, Gifford’s Flowers will guide you in using dried flowers to design a festive grapevine wreath.
Free Portland Trivia w/ Bridgetown Trivia | Sundays-Thursdays, Prizes
Bridgetown Trivia is your neighborhood pub trivia game done right.
2025 September Fruit Loop Events in Hood River & Parkdale | U-Pick Apples, Fall Festivals, Hard Ciders & More
Enjoy apple picking, hard ciders, warm apple cider donuts and more along the Hood River Fruit Loop this September!
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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