A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
2026 Biamp Portland Jazz Festival | 50+ shows, 30+ venues feat. St. Vincent, Mavis Staples & More
Tickets on sale now for the 2026 Biamp Portland Jazz Festival! The most artistically diverse lineup yet with 50+ shows across 30+ venues.
Eras in a Glass: A Taylor Swift Wine Pairing @ Hip Chicks Do Wine | 6 Wines Inspired by Taylor Swift Songs
Calling all Swifties! Join us at Hip Chicks do Wine on Friday, February 28th from 2pm–5pm for an afternoon of wine, food, and Taylor-inspired fun.
Wine Wednesdays @ Négociant | Weekly Wine Flights & Tastings, Valentine’s Day
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.
Portland in the News: Black History Month Reads, Goodbye Lloyd Center, Beyond Dry January & More | February 5, 2026
February is Black History Month and the Multnomah County Library has a list of graphic novels by black authors to check out.
Bloody Valentine VHS Swap & Market @ Dots | Bachelorx Auction, DJ Black Planet
Saturday Feb 7th, we have our next VHS Swap and Vendor Market. We have a ton of awesome tape vendors this time around, so you definitely don’t want to miss it.
Portland Winter Light Festival 2026 | 9 Days of FREE, Outdoor Winter Art Across The City
PDXWLF brings art, technology, and inclusivity together, invigorating Portland in the winter.
Amanati @ Nova PDX | Exotic Electronic Music
Amanati, godfather of Exotic Electronic Music, is a symbol of creative power, raw expression, sensuality, and freedom.
Toxic Love @ Darcelle XV Showplace | A Drag & Cabaret Revue
RAE presents this ICONIC Drag & Cabaret, featuring some of your Favorite Local Drag Performers in Portland at Darcelle XV Showplace!
Friday Night Magic: The Gathering @ The EastBurn Public House | Join the Battle!
Shuffle up and let the Magic happen. Come sit in with us for Friday Night Magic. A night of games, good energy, and people who truly support the community.
Win Tickets ($34): 2026 Portland Spring Home and Garden Show @ Portland Expo Center | Showcase Gardens, Floral Fashion Show, Chef Demos
For decades, this beloved event has brought together garden enthusiasts, design lovers, homeowners, remodelers, and local makers, offering fresh ideas, expert advice, and the latest home and garden trends for every skill level.
Weird Portland Pub Tour: Valentine’s Edition in SE Portland | Great Beer + Weird Stories
Looking for a Valentine’s outing that’s anything but ordinary? This is the tour for people who love great beer, weird stories, and Portland’s wonderfully offbeat personality.
Heartbreakers: A Draglesque Love Story @ Echo Theater Company | Love & Lust Inspired Drag/Burlesque
RAE presents this ICONIC Love & Lust Inspired Draglesque Showcase.
Alphaboats: A Maritime Voyage from Anchor to Zulu @ Columbia River Maritime Museum in Astoria | Mixed Media Paintings
Set sail on an alphabetical journey through the world of boats in Alphaboats: A Maritime Voyage from Anchor to Zulu, a vibrant mixed-media exhibition by Portland artist Peggy Biskar.
Jade Rabbit x Veganizer 2026 Lunar New Year Banquet | Six Course Menu of Lunar New Year Delicacies
Join us as we usher in the Year of the Fire Horse with a six course menu of Lunar New Year delicacies.
Blueprint Ensemble Arts presents Shadow & Light | FREE, Live Music, Dessert
Come join ensembles Carnation, Peach, Scarlet, and Burgundy (with special guests Ivory and The Super Cuts) as they bring you our upper voices masterwork for 2026: Arnesen’s stunning Stabat Mater!
Drag Brunch @ The Pharmacy | Hosted by Devlin Lynn Phoenixx
The event is hosted by Rose Empress LXV, Devlin Lynn Phoenixx with a rotating cast for each event sure to dazzle you with their everything!
2026 Valentine’s Day Dinner @ The EastBurn Public House + Anti-Valentine’s Day Party | Dinner, Brunch, Specials
Celebrate your sweetie with brunch, dinner and drinks in the beautiful EastBurn dining room!
Win Tickets ($56): Jeremy McComb’s Honky-Tonk Circus @ Mission Theater | The #1 90’s Country Music Experience
The Honky-Tonk Circus Tour isn’t a throwback – it’s a full-throttle time machine to the nights when country music ruled the room.
Win Tickets ($80): Heated Rivalry: A Jockstar Rave @ Crystal Ballroom | A Night of Party Boy Anthems & Club Hits
From the Closet → Ice → Dance floor.
2026 Oregon International Auto Show @ Oregon Convention Center | Cutting-Edge Tech, Ride & Drive Experiences, Kids’ Zone & More
The 2026 Oregon International Auto Show is the largest auto show in the Pacific Northwest, showcasing the newest in-vehicle design, innovation, and technology.
Win Tickets ($80): Katie Boyle @ Mission Theater | Irish Comedian
Katie Boyle is an Irish comedian living in New York City. Her favorite stand-up topics are her journey through American culture, dating, therapy and shame!
Win Tickets ($56): The Ramona Flowers @ Mission Theater | Indie Rock
The Ramona Flowers are on a roll – their latest release Human is climbing up the US Alt Radio charts and hitting over 1 millions global streams, and track Dangerous hit the Top 30 at US Alt Radio.
Win Tickets ($46): Alex Sampson @ Mission Theater | Canadian Singer-Songwriter
With humble small-town beginnings, Canadian singer-songwriter, Alex Sampson knew he was born to perform at just nine years old when he entered a school talent show for the first time singing GOLD by Owl City.
My Petty Valentine @ Badlands | Feat. King of Drag Season One Winner King Molasses
Join some of your Favorite Local Drag Icons for Pettiest Valentine’s Celebration in Portland! Mystery Headliner To Be Revealed!
Valentine’s Sweetheart Tea @ Victorian Belle | 3 Floor Mansion, Sweet & Savory Pastries
The Victorian Belle’s Sweetheart Tea is a fun and elegant way to celebrate Valentine’s, Galentine’s Day and more in February!
Rose City Circus presents Valentine – A Night of Circus, Music & Love @ Alberta Rose Theatre | Live Music, Aerialists, Jugglers & More
Rose City Circus and Trashcan Joe present a vintage themed night of love, spotlighting a daring and romantic circus alongside live original tunes of vintage swing, jazz, folk, and blues.
Win Tickets ($90): Chocolate & Wine Pairing @ Hip Chicks Do Wine | 4 Wines + 4 Truffles
Join us for a decadent Wine & Chocolate Pairing featuring artisan truffles from Creo Chocolates paired perfectly with our handcrafted wines.
Win Tickets ($48): Wheel w/ Sound and Shape @ Mission Theater | Prog-Metal
Since forming in 2015, Wheel have swiftly grown from underdogs of Helsinki, Finland, to an international tour de force.
Win Tickets ($56): Kerosene Dream’s Annual Reunion Show @ Mission Theater | Country, Folk, Rock, Pop
Over 25 years ago Dave Coey (guitar, vocals) from The Renegade Saints joined forces with Bart Ferguson (vocals) from The Strangers and played their first gig as Kerosene Dream.
Friends of the Library Media Sale @ Rose City Reads | Valentine’s Gift Ideas, 50% Off Vinyl, DVDs, & More
Head to Rose City Reads this Valentine’s Day weekend for 50% off All DVDs, CDs, LPs, and Sheet Music!
Watch 2026 Superbowl LX in SE Portland @ The Automatic Bar | Sound On, Food & Drink Specials
Cheer on the Seattle Seahawks and New England Patriots while enjoying delicious food and drink specials at The Automatic Bar.
Spellbound: An Evening Of Dark Decadence @ Nova PDX | Goth Music, Burlesque, Aerial Arts
Something hauntingly beautiful approaches… A dazzling spectacle of shadow and desire. Friday The 13th has not fallen upon a February in eleven long years, and the Witches of the West will not let it go to waste.
Win Tickets ($114): Bikini Kill @ Crystal Ballroom | Feminist Punk Rock
Bikini Kill is a feminist punk band that started in Olympia, WA, and later moved to Washington, DC.
Radical Harvest Valentine’s Day Market @ Allgood Brewing Co. | 40+ Makers, Love Potion Bar, Flash Tattoos & More
Radical Harvest is more than a retail experience – it’s a pop-up community center!
Matteo Lane – We Gotta Catch Up! Tour @ Arlene Schnitzer Concert Hall | Podcaster, Comedian, Opera Singer
Matteo Lane brings his We Gotta Catch Up! Tour to Arlene Schnitzer Concert Hall on February 27, and it’s a must-see for comedy fans.
2026 Past to Present Lecture Series @ Columbia River Maritime Museum in Astoria | Historians, Bar Pilots, Vanport Descendants & More
The Columbia River Maritime Museum’s Past to Present Lecture Series returns for 2026!
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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