A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
Win Tickets ($70): Brent Gunter: Trade Winds Premiere Concert @ Newmark Theatre | Flamenco-Inspired Guitar, Melodic Rock
On May 15, composer and guitarist Brent Gunter will premiere his new instrumental album Trade Winds in a special live concert production at the Newmark Theatre.
Win Tickets ($60): 2026 McMenamins UFO Festival @ Hotel Oregon in McMinnville | Alien Costume Ball, Parade, Live Music & More
Get ready, earthlings: The 26th Annual UFO Fest will be landing soon for three days of out-of-this-world fun!
CANCELED – Win Tickets ($46): Alt Bloom @ Mission Theater | Alternative Soul
Alt Bloom is an alternative soul artist from Montana who discovered his passion for music at a young age singing and playing with anyone he could while growing up.
2026 Camas Plant & Garden Fair | Kids Activities, Live Music, Food & More
Held the day before Mother’s Day, the plant fair draws in thousands of people to enjoy and explore the amazing selection of plants, trees, garden art and supplies, and much more provided by our dedicated local growers and vendors.
Win Tickets ($46): Caroline Kingsbury: Shock Treatment Tour @ Mission Theater | Indie Pop
Expect a larger-than-life energy to her iridescent make-up, Bowie-esque boot-and-blazer get-ups and ready-to-risk-it-all ballads that are abundant in brutally honest and vulnerable storytelling lyrics.
Bubbles & Bites @ Hip Chicks Do Wine | 2026 Mother’s Day Weekend
Celebrate Mom all weekend long at Bubbles & Bites at Hip Chicks do Wine!
Farmhouse Kitchen x Veganizer | $45 for 5 Vegan + Gluten-Free Small Plates
From Sunday, April 26 to Sunday, May 3, enjoy the Farmhouse Kitchen x Veganizer menu with creamy tom kha soup, vibrant veggie fresh roll, refreshing pomelo salad, spicy tom yum mapo tofu
Win Tickets ($20): Club Curfew: The 90s w/ DJ Gregarious @ Crystal Ballroom | A Happy Hour Dance Party
Join us for a monthly Happy Hour dance party with DJ Gregarious where your night and your weekend starts EARLY!
Win Tickets ($70): Gus Constantellis – The Book Tour @ Mission Theater | Greek American Stand-Up Comic & Cookbook Author
Gus Constantellis (he/him) is a gay, first generation Greek American stand up comedian and writer raised in Brooklyn, whose sharp, fast paced comedy draws from his loud immigrant family, Greek heritage, and raunchy yet relatable dating stories.
Portland in the News: Farmers Market Turns 20, Champagne, Historic Gayborhood Revival & More | April 23, 2026
Portland’s Montavilla Farmers Market celebrates 20 years of slinging local goods. Bridgetown Bites sat down with one of the market’s founders Lisa Hebert to discuss the market’s rich history. Time to pop bottles! National Geographic has named Oregon’s Willamette Valley as the next Champagne region. And a new bar hopes to restore downtown Portland’s former…
Portland Choir & Orchestra presents Prairie Fire: An American Frontier @ Rolling Hills Church in Tualatin OR | Internationally Recognized Principal Cellist Carter Brey
Internationally recognized and Principal Cellist, Carter Brey, currently performing with the New York Philharmonic Orchestra headlines a Limited Engagement concert, “Prairie Fire – An American Frontier Rhapsody”, with the Portland Choir & Orchestra.
Win Tickets ($44): Love Isn’t Blind @ Sentinel Hotel | A Comedy/Dating Show Where the Men Can’t Speak
In this dating experiment, men compete on stage for one lucky bachelorette, with the little caveat that the men can’t speak.
Win Tickets ($40): Fox Walker w/ Hard Maybe & Zyanna @ Showbar | Neo Soul Night
Fox Walker is a large R&B/Neo-Soul band from Portland, OR, bringing the message of community, authenticity, and self-confidence through music.
Oregon Metro Future Vision Survey | What Should Portland Look Like in 50 Years?
Metro is bringing people together to create the Future Vision, a 50-year vision for the greater Portland region. We want to hear from you!
2026 River Cruises @ Island Style Charters | Tiki Nights, Sunset Cruises, Mother’s Day, Memorial Day Weekend, & More
Experience Portland like never before aboard Island Style Charters! From Happy Hour to Family Fun, there’s a cruise for everyone!
Jekyll In Chains @ Samaritan Odd Fellows Lodge in Milwaukie OR | Musical Reimagining of Dr. Jekyll & Mr. Hyde
A thrilling and original musical reimagining of Robert Louis Stevenson’s cerebral horror masterpiece “The Strange Case of Dr. Jekyll and Mr. Hyde,””Jekyll in Chains” is set in 1990’s Seattle to grunge and alt rock music inspired by bands like Nirvana, Soundgarden, Alice in Chains, Garbage, and more.
2026 Spring Garden Fair @ Clackamas County Event Center | 125 Local Nurseries, Artisans, Garden Art & More
Explore the PNW’s favorite garden event in Canby—it’s worth the drive! We have over 125 local nurseries featuring your favorite plants, alongside local artisans offering unique garden art.
Win Tickets ($40): Crafty Wonderland Spring Art + Craft Market @ Oregon Convention Center | 250+ Makers, Mother’s Day Gifts, Shop Local!
Shop local and find the coolest handmade gifts from over 250 amazing artists!
Win Tickets ($46): Never Ending Fall @ Mission Theater | Alternative/Indie
Formed in the 4th grade, Never Ending Fall (NEF) is an indie-rock band comprised of lead singer and guitarist Jack Miller, drummer Tommy StClair, guitarist and keyboardist Conrad Boyd, guitarist Pearce Eisenhardt, and bassist and vocalist Johnny Hohman.
2026 Gorge Artists Open Studios Tour | 50 Artists, 41 Open Studios
This is an annual free self-guided event that has become a spring tradition in the Gorge.
Win Tickets ($56): Girl Trouble w/ The Mistons & Have You Eaten @ Mission Theater | Northwest Garage Rock
Girl Trouble, Northwest garage rock demigods, return to Portland for one evening, Saturday, June 6, 2026 at McMenamin’s Mission Theater.
Win Tickets ($56): Baby Bugs w/ Elliot Lee @ Mission Theater | Indie, Dark-Pop, Punk
Baby Bugs is an alternative music project founded by Bowie.
Portland in the News: Wacky Cat Names, Drag Hiking, New Botanical Garden & More | April 16, 2026
Portlanders love drag and hiking. It was only a matter of time before the two pastimes met at Drag Me Outside.
Win Tickets ($200): A Taste of Ireland – The Irish Song & Dance Sensation @ Newmark Theatre | World Champion Irish Dancers
A Taste of Ireland brings an extraordinary night of world champion Irish dancers, live musicians and vocalist to Portland’s Newmark Theatre for one performance only on Sunday May 3.
Win Tickets ($20): 2026 Lilac Days @ Hulda Klager Lilac Gardens in Woodland WA | Plant Sale, Mother’s Day, Museum, House Tours
Each year in the spring, the Hulda Klager Lilac Gardens hosts Lilac Days to celebrate the beauty of lilacs in bloom.
2026 82nd Avenue of Roses Parade | FREE, Carnival, Food Carts, Car Show & More
The 20th year theme: “History of East Portland,” because many neighbors who represent this diverse community are new to East Portland.
Free Portland Trivia w/ Bridgetown Trivia | Sundays-Thursdays, Prizes
Bridgetown Trivia is your neighborhood pub trivia game done right.
Sexy Sequins @ Club Privata | PNW’s Premier Lifestyle Club
Prepare to dazzle and shine at ‘Sexy Sequins,’ the ultimate nightclub party where glamour meets seduction.
Wicked Craft Beltane Night Market @ Rae Loft | 30+ Vendors, Goddess-Themed Drinks, Music
Wicked Craft: Bazaar and Craft Fairs are a seasonal market series that focuses on supporting women-owned businesses and artists.
Spring Sip & Stroll in Historic Aurora OR | 8 Wineries, Sweet & Savory Samples, Gift Certificates & More
Grab your pals and get tickets for this antique and vintage filled wine walk event!
Engineering Careers for a Sustainable Future Networking Event @ Revolution Hall | Panel, Q&A, Breakout Sessions
If you’re curious about engineering careers in Oregon, save the date for April 30!
2026 Plant and Vegan Bake Sale @ House of Dreams Cat Shelter | Pots, Garden Art, Treats & More
Indoor/outdoor plants, pots, garden art and delicious vegan baked goodies. Great selection and amazing low prices – for a wonderful cause.
The SpongeBob Musical @ Portland Playhouse | Tony Award-Winning Musical
The end of the world is coming. At least, that’s what the citizens of Bikini Bottom believe when a volcano threatens to wipe them off the map.
Win Tickets ($46): One Way Out @ Mission Theater | Allman Brother’s Tribute
One Way Out PDX is the Portland, OR based 8-member powerhouse tribute to the music of the great Allman Brothers Band.
2026 Portland Cinco de Mayo Festival @ Tom McCall Waterfront Park | Celebration of Mexican Culture, Music & Cuisine
The Portland Guadalajara Sister City Association (PGSCA) invites you to the 39th Annual Portland Cinco de Mayo Fiesta, a celebration of Mexican culture, music, and cuisine at the scenic Tom McCall Waterfront Park.
Win Tickets ($48): Steal Your Bass & Jerry’s Pickle @ Mission Theater | Grateful Dead Cover Bands
Steal Your Bass isn’t your typical Grateful Dead cover band- they’ve reimagined the entire sonic landscape of the Dead’s music by replacing the traditional lead guitar with a lead bass bringing the music to new depths.
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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