A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!
Mt Hood Repertory Theatre presents Silent Sky @ OMSI’s Kendall Planetarium | Celestial Visuals, Live Music
Mt Hood Repertory Theatre is producing Silent Sky by Lauren Gundersen in partnership with OMSI.
Last Thursday Art Opening @ The Goodfoot | Featuring: Alan Rose, Brett Bowers, Ian Jankowski-Seniff
The Goodfoot will have an art opening last Thurs Feb 27th. the show will be up until March 23rd.
2025 Oscar Trivia & Viewing Party @ The EastBurn Public House | Shanrock’s Trivia, Prizes, Costumes
It is time for our annual Oscars shenanigans!
Win Tickets ($44): Sydney Sprague w/ Pony @ Mission Theater | Indie Pop
Sydney Sprague channels her sadness, anxiety, and existential dread through driving guitars, shimmering melodies, and the deceptively sweet weapons of indie pop-rock and keen observation.
Free Improv Workshop @ Deep End Theater | Lead by Domeka Parker (Artistic Director)
Join us for a fun afternoon of play! In this workshop we will dip our toes into Deep End’s unique improv style.
Portland in the News: PDX Jazz Festival, Baby Elephant, Timber Jim & More | February 20, 2025
In case you need a pick me up, Oregon Zoo’s newest elephant calf Tula-Tu will be on display to visitors for the first time this Friday.
Clash of the Trivia Titans @ Spare Room | Shanrock’s Triviology 20th Anniversary
This is the Super Bowl of trivia; the Oscars of pub quizzery…there will be one team to rule them all!
Win Tickets ($87): Bruce Cockburn @ Aladdin Theater | Folk, Jazz, Rock
Bruce Cockburn’s latest studio album, O Sun O Moon, is a testament to his enduring artistry, even as he nears his 78th birthday.
Portland’s Pettiest Drag Show @ Escape Bar & Grill | Hosted by Savannah O Bennington
Portland’s Pettiest Drag Showcase, featuring some of your Favorite Local Drag Performers. Hosted By Savannah O Bennington.
Artists Repertory Theatre presents Sapience | By Diana Burbano, Directed by Melory Mirashrafi
Elsa is a primatologist studying the language abilities of orangutans, like her subject Wookie who yearns for connection with humans.
Win Tickets ($54): An Evening with Fink @ Aladdin Theater | Music has been featured in The Walking Dead, True Detective
Fink, AKA Fin Greenall, is a singer-songwriter from Cornwall, UK, currently based in Berlin.
Win Tickets ($87): Bored Teachers: The Struggle is Real Comedy Tour @ Revolution Hall | #1 Ranked Teacher-Comedy Podcast
Bored Teachers are BACK with all new material on their “The Struggle is Real!” Comedy Tour.
Win Tickets ($52): Matt Braunger @ Aladdin Theater | ABC’s Agent Carter, NBC’s Up All Night, Comedy
Matt Braunger was raised in Portland, Oregon. A headlining comedian since 2007 and an actor since childhood, Matt studied theatre in New York and improvisation in Chicago.
Glamorous Glitter @ Club Privata | Pacific Northwest’s Upscale Lifestyle Nightclub
Close out your February at the Pacific Northwest’s Upscale Lifestyle Nightclub and wear your most glamorous glitter attire!
Wine on the Water @ Portland Spirit | Sunset Cruise w/ 14 Local Wineries
Taste your way through Oregon on this sunset wine tasting cruise aboard the Portland Spirit! More than a dozen local wineries will be on board to showcase their latest vintages.
Win Tickets ($50): 2025 Hortlandia @ Wingspan Event Center | Indoor Plant & Garden Art Sale
Take a break from the rain and come inside to HORTLANDIA. Explore boutique nurseries, gardening equipment makers, gardening books (used and new), the HPSO botanical display, our nonprofit community partners, and garden-themed artwork.
Cappella Romana presents Canon for Racial Reconciliation @ First United Methodist Church | Choir & Gospel Instrument Ensemble
Cappella Romana invites you to experience a groundbreaking fusion of traditions with the Pacific Northwest première of the complete Canon for Racial Reconciliation for choir and gospel instrument ensemble!
Win Tickets ($50): The Hails, Never Ending Fall @ Mission Theater | Indie, Punk
March 12 @ Mission Theater – There has always been a strange air about the sequence of events meant to unite Robbie Kingsley, Franco Solari, Dylan McCue, Andre Escobar and Zach Levy, that begs the question, is anything ever truly up to chance?
Win Tickets ($70): The Devil Makes Three @ Crystal Ballroom | Folk, Blues, Ragtime, Rock N Roll
March 1 @ Crystal Ballroom – With six studio albums and almost 20 years under their belt, longstanding Americana triumvirate The Devil Makes Three (TDM3) continues to write, tour, and play as hard as ever they have.
Portland in the News: Crow City, PDX Monopoly, Jazz Festival & More | February 13, 2025
Snow has arrived in Portland! If you have the right gear and safe road conditions, Travel Portland has a list of stunning winter waterfalls to visit.
Underground Drag & Comedy Show 3 Year Anniversary Edition @ UnderBar | Hosted By Savannah O Bennington
From our sponsors: Underground Drag & Comedy Show 3 Year Anniversary Edition February 22, 2025 9-11pm | $15 | 21+ Purchase Tickets: eventbrite.com UnderBar 1701 1/2 Broadway St, Vancouver, WA 98663 UnderBar’s Monthly Drag and Comedy Showcase, featuring some of your Favorite Local Drag Performers. Hosted By Savannah O Bennington
Sword & Veil Presents Carnivàle @ Victorian Belle | Dancing, Costume Contest, Vendors
Sword and Veil, a themed costume soirée at a haunted mansion held quarterly at the stunning Victorian Belle Mansion in North Portland’s Kenton neighborhood, presents Carnivàle
Free Portland Trivia w/ Bridgetown Trivia | Sundays-Thursdays, Prizes
Bridgetown Trivia is your neighborhood pub trivia game done right.
2025 Biamp Portland Jazz Festival | Feat. Erykah Badu, 70+ Events, 35+ Venues
The 2025 Biamp Portland Jazz Festival, presented by PDX Jazz, is coming February 20 – March 1 with 70+ events!
Win Tickets ($24): Company Grand w/ River City Riot @ The Goodfoot | Rock & Roll, Blues, Funk
Bend’s Company Grand is an exhilarating 9-piece band that was founded during the Summer of 2014.
Win Tickets ($30): Goodfoot 24 Year Anniversary Show w/ Patterns Fly @ The Goodfoot | Organ Trio Funk, Psychedelic
Help us celebrate our birthday with the astounding Patterns Fly!
Hearts of Horror @ Cinema of Horrors Haunted House | Valentine’s Haunted Attraction, Kissing Booth, Chocolate
Celebrate Valentine’s Day with a spine-tingling twist at Hearts of Horror in Kelso, WA! This February, discover a hauntingly romantic experience
2025 President’s Day Brunch @ The Eastburn Public House | Mimosas
The Eastburn Public House will be open for President’s Day Monday, February 17, from 8AM-3PM.
Win Tickets ($80): Reverend Horton Heat @ Crystal Ballroom | Blues, Rockabilly
February 27 @ Crystal Ballroom – Reverend Horton Heat a time-travelling space-cowboy on a endless interstellar musical tour, and we are all the richer & “psychobillier” for getting to tag along.
Win Tickets ($70): Emmy Winner Ben Bailey @ Mission Theater | ‘Cash Cab,’ Comedy Central, The Tonight Show
February 28 @ Mission Theater – Ben Bailey is best known for hosting the Emmy Award-winning game show Cash Cab in New York City.
Win Tickets ($30): 2025 Portland Spring Home & Garden Show | Workshops, Floral Installations, Plant Shopping
The 2025 Portland Spring Home & Garden Show presented by Standard TV & Appliance launches the spring season in Portland, with four days of home and garden inspiration – Thursday, February 20 through Sunday, February 23 at the Portland Expo Center.
Win Tickets ($36): The Velveteers: A Million Knives Tour @ Mission Theater | Indie, Rock
March 6 @ Mission Theater – The Velveteers bring a visceral energy to their explosive sophomore album, A Million Knives, loaded with blistering rock anthems infused with melodic indie songwriting.
Keepin It Klassy Drag & Comedy Show @ Escape Bar & Grill | Hosted by Nashville Hott
Escape Bar and Grill’s Monthly Drag & Comedy Showcase. Hosted By The Queen Of The Trailer Park, Nashville Hott!
Win Tickets ($70): Socks in The Frying Pan @ Mission Theater | Traditional Irish Folk
March 4 @ Mission Theater – Socks in The Frying Pan combines virtuosic musicianship with a burning passion for the music and tradition, pitch-perfect harmonies, and a big splash of quick wit and banter.
Win Tickets ($74): Two Feet: The Next Steps Tour @ Crystal Ballroom | Alternative/Indie
Zachary William ‘Bill’ Dess, known by his stage name Two Feet, is an American singer, songwriter, and producer from New York City.
2026 Winter Music Festival @ Milwaukie Elks Lodge | Live Music, Food, Drinks
Winter Music Festival founder and coordinator LeeAnn Gibbons and her music loving and festival following pals found themselves commiserating about the lack of music festivals during the colder months.
THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!
| Today
Scooped Ice Cream Festival @ Esther Short Park in Vancouver, WA | 50+ Flavors of All You Can Eat Ice Cream
| Food & Drink
Chamber Music Northwest presents CONFLUENCE: Our Shared Voices 2026 Summer Festival | 70 of the world and our region’s finest chamber musicians!
| music
Tea Fest PDX @ World Forestry Center | A Celebration of Tea Culture
| events, Food & Drink
St. Helens Independence Day Celebration 2026 @ Columbia View Park | Music, Food, and Activities for All Ages
| All Ages, events, Free
Win Tickets ($160): 2027 Portland Folk Festival @ Crystal Ballroom | 30+ Local & National Artists
| music
Win Tickets ($86): McMenamins Presents Madison Ryann Ward @ Mission Theater | Contemporary Christian, Pop + R&B
| music
Win Tickets ($70): McMenamins Presents “A Hot August Night” with Super Diamond @ McMenamins Grand Lodge in Forest Grove | The Neil Diamond Tribute
| music
Portland in the News: Waterfront Restaurant, Airport Accolades, Heatwave & More | June 11, 2026
| News
McMinnville Art Festival @ Downtown McMinnville | 50+ Artists & Artisans, Interactive Kids’ Crafting, Art Demos, & More
| All Ages, events, Free, Shopping, Visual Art
PRIDE at the Museum @ OMSI | A night at the museum celebrating the LGBTQ+ Community
| All Ages, events, Food & Drink, LGBTQ, Science, Shopping
Villain Arts Tattoo Festival @ The Rose Quarter | Celebrate the Art of Tattooing
| All Ages, events, Services, Shopping
Keep in Touch!
Subscribe to our e-mail newsletter to receive updates