THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!

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A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!

2025 Portland Regional Gem & Mineral Association Annual Show @ Wingspan Event and Conference Center | Geology & Paleontology Exhibits

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The Portland Regional Gem & Mineral Show is hosted every October by 5 area non-profit clubs. This is a family-friendly event focused on Geology and Paleontology.

2025 Ghosts of the Grand in Salem | Immersive Haunted House

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Step into Salem’s historic Grand Theatre for Ghosts of the Grand – an immersive haunted house where ghost hunting collides with forbidden rituals.

Win Tickets ($54): Hood River Orchard & Ale Festival | Fresh Hop Beers & Fall Ciders

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Get ready, Hood River — a fresh new tradition is brewing! This fall, we’re raising a glass to two of the Pacific Northwest’s most iconic seasonal offerings: crisp craft ciders and fresh hop beers.

Win Tickets ($20): The Walkaways @ The Goodfoot | Phish Covers Cover Band

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The Walkaways are Portland’s Phish covers cover band (they play the covers Phish themselves play).

The Bed Trick @ Artists Repertory Theatre | Effervescent Bedroom Farce by Seattle’s Keiko Green

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Ahh, the old bed trick… When Person A tricks Person B into sleeping with them by pretending to be Person C. Classic!

Last Thursday Art Opening @ The Goodfoot | Feat. Heide Davis, Mary Undercoffer-Gallop, Olivia Bailey, Tyler Corbett

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The Goodfoot will have an art opening last Thursday Sept 25th, the show will be up until Oct 26th.

Love, Shakespeare presents “Kill Will” @ Portland Center Stage | An Unpredictable Tribute to Shakespeare

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Step into the offbeat world of Love, Shakespeare, where seasoned Portland comedians attempt something audacious: making up a Shakespeare-style play based only on your suggestions!

Win Tickets ($96): Golden Girls: The Laughs Continue @ Newmark Theatre | Miami’s Sassiest Seniors Live

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The Golden Girls are back in an all new show! 2025 finds Sophia out on bail, after being busted by the DEA for running a drug ring at Shady Pines.

Portland in the News: Mushroom Foraging, Majestic Elk, Tom Hanks & More | September 18,2025

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Did you know you can see Oregon’s largest land animal on the Oregon Coast? Learn how to spot the regal Roosevelt Elk safely on your next vacation.

Win Tickets ($120): Paradise Blue @ Portland Playhouse | Noir Inflected Musical Drama

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Step into a world of jazz, found family, and the inspiring resilience of a community on the brink.

Win Tickets ($108): Kathleen Madigan: The Day Drinking Tour @ Arlene Schnitzer Concert Hall | American Comedy Award for “Best Female Comedian”

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Comedian Kathleen Madigan’s 33-year comedy career is showing no signs of slowing down as she is on her all-new tour, The Potluck Party Tour in 2024.

Win Tickets ($72): Esther Povitsky: The Pretty Little Baby Tour @ Aladdin Theater | Variety’s “10 Comics to Watch”, Trash Tuesday Podcast

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Esther Povitsky’s stand up special for comedy central titled HOT FOR MY NAME currently streams on Paramount Plus and Youtube.

Win Tickets ($120): Mary Shelley’s FRANKENSTEIN @ Experience Theater Project | Immersive Promenade Performance

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Prepare to witness Frankenstein like you’ve never seen it before. This is not a show you simply sit and watch.

A Tim Curry & Tim Burton Inspired Drag & Burlesque Show + All Ages Spooktacular @ Echo Theater Company | Costume Contest, Trick or Treat & More

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“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

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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

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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!

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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

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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

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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

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Join Oregon Humane Society for the return of Bowser’s Boo Bash!

Win Tickets ($60): Maris + Caroline Kingsbury @ Mission Theater | Queer Power Pop

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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.

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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

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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

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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

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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.

THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!

A round up of what's going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!

Scooped Ice Cream Festival @ Esther Short Park in Vancouver, WA | 50+ Flavors of All You Can Eat Ice Cream

July 18-19 - The Pacific Northwest's premier ice cream festival is back at Esther Short Park in Vancouver, WA for two all-you-can-eat days of scoops, live music, and summer fun. Scooped! returns July 18 and 19, 2026, 11:00 AM to 7:00 PM — and your ticket includes unlimited ice cream from 50+ flavors served up across Scoop Valley.

Chamber Music Northwest presents CONFLUENCE: Our Shared Voices 2026 Summer Festival | 70 of the world and our region’s finest chamber musicians!

Music has the ability to connect us beyond words, labels, and borders, inviting us to celebrate both our differences and our common ground.

Tea Fest PDX @ World Forestry Center | A Celebration of Tea Culture

June 27 - TeaFestPDX is more than a festival, it’s a community.

St. Helens Independence Day Celebration 2026 @ Columbia View Park | Music, Food, and Activities for All Ages

July 4 - Celebrate the Fourth of July at Columbia View Park in St. Helens, Oregon – one of the most scenic Independence Day destinations in the Pacific Northwest.

Win Tickets ($160): 2027 Portland Folk Festival @ Crystal Ballroom | 30+ Local & National Artists

January 30 - An annual celebration of folk and Americana music showcasing 30 local and national artists hosted by the historic Crystal Ballroom.

Win Tickets ($86): McMenamins Presents Madison Ryann Ward @ Mission Theater | Contemporary Christian, Pop + R&B

September 4 - Faith-based singer/songwriter Madison Ryann Ward writes warmhearted songs that mix mature pop and contemporary R&B with accents of gospel, blues, and folk.

Win Tickets ($70): McMenamins Presents “A Hot August Night” with Super Diamond @ McMenamins Grand Lodge in Forest Grove | The Neil Diamond Tribute

August 22 - An uncanny tribute to beloved master singer/songwriter/performer, American pop icon Neil Diamond – Super Diamond has appeared on The Late Show with David Letterman, CNN, VH1, Fox News, and Comedy Central, and has been featured in publications such as Rolling Stone Magazine, The New York Times, and the San Francisco Chronicle.

Portland in the News: Waterfront Restaurant, Airport Accolades, Heatwave & More | June 11, 2026

The Portland Spirit has big plans to open a new restaurant in the former Rose Festival headquarters in Tom McCall Waterfront Park. 

McMinnville Art Festival @ Downtown McMinnville | 50+ Artists & Artisans, Interactive Kids’ Crafting, Art Demos, & More

July 18-19 - Celebrate creativity in the heart of Oregon wine country at the McMinnville Art Festival, a free two-day outdoor event showcasing the work of talented artists and artisans from across the region.

PRIDE at the Museum @ OMSI | A night at the museum celebrating the LGBTQ+ Community

June 12 - Celebrate PRIDE at the Museum with an evening of science, community, and joyful exploration!

Villain Arts Tattoo Festival @ The Rose Quarter | Celebrate the Art of Tattooing

July 17-19 - Tattooing is more than body art—it’s a global language of identity, resilience, and self-expression.

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