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 Winter Market @ Brentwood Darlington Community Center | Handmade Goods, Holiday Treats, Kids Market

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The Brentwood-Darlington Winter Market returns for its 3rd year! This neighborhood favorite brings together local makers, artists, and small businesses for a cozy day of community and creativity.

Holiday Afternoon Tea @ Victorian Belle | Holiday Decor, Sweet & Savory Pastries, Wine

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The Victorian Belle’s Holiday Afternoon Tea is a fun and elegant way to celebrate the holidays!

Win Tickets ($62): Portland’s Singing Christmas Tree @ Sunset Church | Music, Dance & Pageantry

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Experience the JOY of Christmas at Portland’s Singing Christmas Tree 2025 concert series!

A Christmas Carol @ Portland Playhouse | Timeless Holiday Classic

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The timeless holiday classic A Christmas Carol returns to Portland Playhouse, relating the story of Ebenezer Scrooge, a wealthy and miserly businessman who ultimately experiences redemption.

Wicked Craft: Holiday Bazaar & Craft Fair @ Rae Loft | Local Makers, Food, Drinks, Food Drive

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This is our seasonally inspired Holiday Craft Market. Come ready to shop for amazing artisanal gifts, crafts, sundries, and art! Support local artists and small business owners.

Win Tickets ($64): Zepparella @ Aladdin Theater | All-Female Led Zeppelin Tribute

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How to honor the legacy of a band deemed sacred? To tread on holy ground is perilous, and must be done with the intent and spirit of a disciple.

Win Tickets ($120): The Mountain Goats @ Revolution Hall | Indie, Folk

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There are Mountain Goats albums that emerge from historical deep dives, vividly rendered autobiography, liturgical exploration, and modern anthropological study.

Win Tickets ($64): Jens Lekman w/ Jordan Patterson @ Aladdin Theater | Swedish Pop Musician & Accidental Wedding Singer

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Jens Lekman is an accidental wedding singer. But he’s also a wedding singer for a reason.

Win Tickets ($70): 2025 Portland Holiday Brew Fest @ Pioneer Courthouse Square | 40+ Beers, 75 -Foot Christmas Tree, Vinyl DJs

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Portland Holiday Brew Fest is pleased to partner with The Square to bring holiday beer and cheer to downtown!

Portland in the News: Pikas Are Back, Exploding Whale Day, Comic Museum & More | November 13, 2025

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It’s getting cuter in the Columbia River Gorge these days. The Oregon Zoo’s Cascades Pika Watch reports the potato-size mammals are making a population comeback after the 2017 Eagle Creek Fire caused their numbers to dwindle. Oregonian’s celebrated the 55th anniversary of Exploding Whale Day this week and an official celebration will be held in Florence…

Win Tickets ($60): Taylor Acorn w/ WILT @ Aladdin Theater | Pop-Punk

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Taylor Acorn is a singer-songwriter whose emotionally raw music has connected with fans around the world.

Win Tickets ($172): Built to Spill w/ Larry Yes & Papas @ Revolution Hall | Indie Rock

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Built to Spill was formed in 1993 by Doug Martsch and over the years they have toured extensively and made several albums with a rotating cast of musicians

MagicSpace presents STOMP @ Keller Auditorium | International Percussion Sensation

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STOMP is explosive, provocative, sophisticated, sexy, utterly unique and appeals to audiences of all ages.

Portland Spirit Presents 2025 Cinnamon Bear Holiday Breakfast Cruises in Downtown Portland | Storytelling, Music, Magic

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Join us on our 20th year anniversary for a beloved holiday event for kids and grandparents alike!

Support Your Local Library This Holiday Season w/ Friends of the Library | Used Books, Cards, Locally Made Gifts

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Support local this holiday season w/ Friends of the Multnomah County Library. These are gifts with a purpose, with proceeds benefiting the Multnomah County Library.

Holiday Table Tasting @ Packer Orchards | Sample Pies, Classic Sides, Jams & More

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Join us at the farm for a festive afternoon of sampling our holiday pies, classic sides, jams, and pickled favorites — a true taste of the season!

Win Tickets ($30): 2025 Nouveau Nouveau Fête @ Division Winemaking @ The Wine Yard | Wine Tasting, Oysters, Cheese Plates

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Like the ones made by our friends in Beaujolais, nouveau wines are typically the first wines released from any given vintage, created to celebrate the end of harvest.

Mt. Hood Repertory Theatre presents True West @ Wyrd Hut | Sam Shepard’s Tale of Sibling Rivalry

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Mt Hood Repertory Theatre is excited to announce our first production at The Wyrd Hut. True West by Sam Shepard, directed by Sarah Andrews.

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.

Ladies Night Out @ Club Privata | PNW’s Premier Lifestyle Club

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Everyone is welcome at this special night so dress to impress and step into a world where the men perform for the ladies.

Win Tickets ($80): Joshua Radin w/ Emily James @ Aladdin Theater | Folk Music

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Joshua Radin emerged in 2004 as an empathetic, engaging, and often enthralling troubadour.

Albariza Wine Bar @ Meatstuff | Grilled Whole Duck, Caviar Bumps, Alpine Wines

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A once a month casual good time spent mingling, drinking good wine and grazing on (sometimes unusual) meaty things at a butcher shop. You show up. We pour you wine. We feed you meat.

Win Tickets ($64): Brent Cobb & The Fixin’s – The Ain’t Rocked In A While w/ Me Like Bees @ Aladdin Theater | Country, Soul, Folk Rock

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Buckle up, y’all. Brent Cobb wants to rock. A master storyteller from small-town Georgia who chronicles Southern life in plain-spoken songs

Win Tickets ($136): Of Monsters & Men w/ DJ Gregarious and VJ Disorder @ Crystal Ballroom | Icelandic Indie Folk/Rock

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Of Monsters and Men went from Reykjavík to the global stage with their breakout 2011 debut My Head Is An Animal, which propelled them from Icelandic indie darlings to international chart-toppers.

Win Tickets ($56): On Company Time @ Mission Theater | Musical Comedy Trio

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OCT (On Company Time) is a musical comedy trio blending sharp satire with chart-worthy bangers.

Win Tickets ($120): Steve Hackett: Genesis Greats, Lamb Highlights & Solo @ Revolution Hall | Genesis Guitarist, Prog Rock

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His new show celebrates the 50th anniversary of The Lamb Lies Down On Broadway, and Steve Hackett includes a selection of highlights from this iconic Genesis album.

Win Tickets ($72): The Happy Fits w/ Krooked Kings & Double Standard @ Revolution Hall | Indie Rock

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Since their 2018 debut, The Happy Fits have cemented their place as a buzzing presence on the indie/alt/rock map with chart-topping releases, worldwide headline tours, festival appearances, and an ever-growing ardent fanbase.

Win Tickets ($64): Jim Norton w/ Sara Weinshenk @ Aladdin Theater | ‘Jim Norton Can’t Save You’

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Jim Norton is a stand-up comedian, radio host, actor, and a twice NY Times bestselling author.

Win Tickets ($56): Ryan Goodcase @ Mission Theater | Youngest Winner of the World Series of Comedy

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Praised for his smart writing and dry delivery, Ryan Goodcase became the youngest person to win the World Series of Comedy in 2019.

25th Annual Pretty Kitty Holiday Bazaar @ Tabor Space | FREE, Handmade Gifts, Refreshments

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The Pretty Kitty Bazaar features handmade gifts and refreshments with all proceeds benefitting House of Dreams.

Portland in the News: Owl Attacks, Free Zoo Admission, Fall Foliage & More | November 6, 2025

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Hoo is an invasive species that likes to pluck hats off of unsuspecting Portland hikers? The barred owl has been on the attack in Oregon since the 70s. 

O Christmas Tea: A British Comedy @ Newmark Theatre | Smash-Hit Holiday Comedy

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Reminiscent of classic British pantos, O Christmas Tea brims with wordplay, physical comedy, and cleverly crafted interactive moments.

Art is King @ Love is King | Art Show, Cocktails, Film Screening & More

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This one-day experience brings together Portland’s most talented designers and makers, each transforming raw materials into works of meaning, beauty, and purpose.

Wine Wednesdays @ Négociant | Weekly Wine Flights & Tastings

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A weekly flight of wines centered around a theme, whether that is a grape varietal, a producer, a region, a style of winemaking or sometimes just the crews’ favorites.

Win Tickets ($68): Lady Wray w/ The Sextones @ Aladdin Theater | Soul + R&B

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Lady Wray is making music on her own terms. With an almighty voice, soul-stirring lyrics, and a magnetic personality, the singer-songwriter continues to elevate her artistry while pushing the boundaries of soul and R&B.

The Aero Space presents Pole Cinema @ Alberta Rose Theatre | Art of the Pole + Movie Soundtracks

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The AERO Space presents Pole Cinema, where silver screen soundtracks come alive through the art of pole—each spin and climb a love letter to the stories that shaped us.

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’s CONFLUENCE: Our Shared Voices 2026 Summer Festival | Experience more than 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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