A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
Win Tickets ($64): Jay Som w/ Sea Lemon @ Aladdin Theater | Indie Rock
Where, you are almost certainly asking, has Jay Som been?
Drag Bingo w/ Peachy Springs @ Showbar | RuPaul’s Drag Race Meets The Price is Right, Prizes
NOW PLAYING weekly at Show Bar inside of Revolution Hall, it’s a DRAG BINGO night like no other!
Win Tickets ($146): Dave Chappelle @ Moda Center | Grammy Award Winning Comedian, Creator of The Chappelle Show
https://www.rosequarter.com/calendar-events/dave-chappelle-dec-5-2025
Portland in the News: PDX Monopoly, Coastal Sharks, Art Museum Upgrade & More | November 20, 2025
Would you like to own the Nines Hotel or Portland Japanese Garden? The first official Portland Monopoly game allows you to do just that.
2025 Holiday Makers Market @ Sustainable NW Wood | 30+ Local Businesses, Food & Drinks, Sasquatch Santa
Now in it’s 5th year, the Holiday MAKERS MARKET at Sustainable NW Wood is lining up to be the BEST YET!
Portland’s Pettiest Drag Pageant @ Escape Bar & Grill | Hosted By Savannah O Bennington
RAE Presents the Pettiest Drag Pageant in Portland! The Audience Picks The Winner! Hosted By Savannah O Bennington.
Free Portland Trivia w/ Bridgetown Trivia | Sundays-Thursdays, Prizes
Bridgetown Trivia is your neighborhood pub trivia game done right.
2025 Vancouver Holiday Market @ Hilton Vancouver | 120+ Local Artisans, Music, Kids Activities, Black Friday & Small Business Saturday Shopping
Celebrate the season at the Vancouver Holiday Market!
Christmas Ships Cruises @ Island Style Charters | Heated Tiki Boat, Warm Drinks
Celebrate the holidays by viewing the Christmas Ships Parade from the best seat in Portland, the water!
Holiday Appetizer & Wine Pairing @ Hip Chicks Do Wine | 4 Bites, 6 Wines, Coat Drive
Need some fresh inspiration for your holiday entertaining? Join us for our Holiday Appetizer and Wine Pairing event!
2025 Christmas Ship Cruises @ Portland Spirit | Dinner Cruises, Hot Chocolate, Live Music
Enjoy the 21st annual Christmas Ship Parade aboard the Portland Spirit! This marks the 71st year of the Christmas Ship Parade in Portland, Oregon.
Small Business Saturday Winter Market @ The Zed | Craft Beer, Food Stalls, Local Makers
Join us at The Zed this Small Business Saturday for a cozy winter artisan market!
2025 Winter Market @ Brentwood Darlington Community Center | Handmade Goods, Holiday Treats, Kids Market
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
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
Experience the JOY of Christmas at Portland’s Singing Christmas Tree 2025 concert series!
A Christmas Carol @ Portland Playhouse | Timeless Holiday Classic
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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.
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
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
Joshua Radin emerged in 2004 as an empathetic, engaging, and often enthralling troubadour.
Albariza Wine Bar @ Meatstuff | Grilled Whole Duck, Caviar Bumps, Alpine Wines
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
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
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.
MANY Weekend Events & Giveaways ($2,400+): Festivals, Fireworks, Concerts, Comedy, Theater, Film, & More!
| Weekend
Portland in the News: State Park Passes, Pink Light District, Swimming Holes & More | July 9, 2026
| News
Win Tickets ($70): McMenamins Presents “A Hot August Night” with Super Diamond @ McMenamins Grand Lodge in Forest Grove | The Neil Diamond Tribute
| music
7 Deadly Sins: CHURCH Part Two: Lust @ PAM-CUT’s Tomorrow Theater | Interactive Storytelling Series
| Comedy, events, music, SE Portland
Portland Sketch Fest @ The Siren Theater | Oregon’s Only Sketch Comedy Festival
| Comedy
Haulin Aspen @ Wanoga Sno Park | Marathon, Half Marathon, 6.5-mile “Half As,” and NEW Three-Person Marathon Relay
| Active Lifestlye, sports
New Portland Jobs: Lan Su Chinese Garden, PHAME, Creo Chocolate & More
| Jobs
Win Tickets ($85): Jerry’s Middle Finger @ Crystal Ballroom | Jerry Garcia Tribute Band
| All Ages, downtown, events, music
Kumoricon 2026 @ Oregon Convention Center | Anime & Japanese Culture Convention
| All Ages, Books, events, Food & Drink, NE Portland, Shopping, Visual Art
Win Tickets ($48): McMenamins Presents Gully Boys @ Mission Theater | Indie Rock
| All Ages, music, NW Portland
2026 Summer Free For All In The Parks: Festivals, Free Movies, Free Concerts, Dance, Theater, Comedy, & More
| All Ages, events, Film, Free, music, Visual Art
Win Tickets ($56): McMenamins Presents The Hails Duck Pond Tour @ Mission Theater | Indie-Rock
| All Ages, music, NW Portland
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