A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
FREE Improv Workshop @ Deep End Theater | Led by Domeka Parker
Join us for a fun afternoon of play! In this workshop we will dip our toes into Deep End’s unique improv style.
2025 GRO Parade of Homes @ The Nines at Camas Meadows | Tour Six Luxury Homes
Explore the essence of refined, modern living at the 47th annual GRO Parade of Homes.
Win Tickets ($24): Shafty @ The Goodfoot | Phish Tribute
Shafty is the Pac NW’s finest Phish tribute band.
The Crystal Gems in the Land of Ooo @ Clinton Street Theater | Drag & Burlesque Inspired By Adventure Time & Steven Universe
For fans, by fans, you’ll see 13 amazing performers with their takes on iconic characters from Adventure Time and Steven Universe.
2025 Labor Day Weekend Cruises @ Island Style Charters | Waterfall & Wine, Sunset Cruise, Happy Hour
Experience Portland like never before this Labor Day Weekend aboard Island Style Charters! From Happy Hour to Family Fun, there’s a cruise for everyone!
Portland in the News: Rocky Horror, Zymoglyphic Museum, Moon Walk & More | August 21 2025
If you’ve ever done the ‘Time Warp’, you may have the Clinton Street Theater to thank.
PICA’s 2025 Time-Based Arts Festival | Performances, Exhibitions, & Interdisciplinary Work, 28 Artists in 10 days
Portland Institute for Contemporary Art (PICA) announces TBA:25, the 22nd edition of the Time-Based Art Festival, taking place from September 4 – 14, 2025 at PICA and around Portland.
2025 Labor Day Weekend Wine & BBQ @ Hip Chicks Do Wine | Wine Tasting Small Plates Discounts
Celebrate Labor Day Weekend with a deliciously fun and flavorful event at Hip Chicks Do Wine!
2025 Rose City Comic Con @ Oregon Convention Center | Comics, Gaming, Cosplay, Anime & More!
Portland’s premier pop culture event, Rose City Comic Con, is produced locally with a weird and wonderful vibe that’s unique to the Pacific Northwest.
Portland Spirit Brews on Board | Taste Beers & Ciders from 12+ Local Breweries
Taste your way through Northwest brews on this craft beer tasting cruise aboard the Portland Spirit!
Win Tickets ($108): Aly & AJ @ Arlene Schnitzer Concert Hall | Sisters Pop-Rock Duo
Platinum-selling sister duo Aly & AJ are hitting the road this fall in support of their new album, Silver Deliverer, and Portland fans will get their chance to experience it live.
Win Tickets ($10): Greaterkind @ The Goodfoot | Jazz Fusion, Funk
Greaterkind features Charlie Brown III, Peter Knudsen, Cory Limuaco, and Ian “Yuck” Lindsay.
Win Tickets ($150): 2025 Italy in the Valley @ Cana’s Feast | Wine, Food, Music
Started in 2009, Italy in the Valley is a celebration of wine, food, music, and friendship.
New Wellness Studio Opening in Beaverton – The Tox Portland Cedar Hills
The Tox Technique is a signature approach to bodywork, blending intentional movement and sculpting methods to support your body’s natural rhythm and flow.
Portland in the News: World’s Ugliest Dog, Trail Blazers Sold, Vegan Fast Food & More | August 14, 2025
What do you get when you cross Batty from FernGully with a shell-less armadillo? Something approximating Petunia, a two-year old English Bulldog from Eugene, who was just crowned World’s Ugliest Dog.
Win Tickets ($24): Deltaphonic w/ Superplume @ The Goodfoot | Rock, Blues, Funk, Soul
At the crossroads of Southern rock, blues, funk and soul, Deltaphonic has spent the last decade developing an unmistakable sound.
Win Tickets ($24): Joslyn & The Sweet Compression @ The Goodfoot | Soul-Funk
A rising force out of Lexington, Kentucky, the band led by Joslyn Hampton come out swinging on their sophomore album, ready to uplift and inspire through their singular and stirring soul-funk sound.
2025 MADE Bike Show @ Zidell Barge Building | 200+ Exhibitors, A Celebration of Craft, Community, and Innovation
Set against the industrial backdrop of the legendary Zidell Yards along the Willamette River, the event offers a unique intersection of artistry, performance, and forward-thinking design in the world of bikes.
2025 Silobration NW @ Abbey Road Farm | Wine, Food Trucks, 40+ Makers
Join us for Silobration NW, a two-day celebration of wine, food, music, and fun at Abbey Road Farm!
Win Tickets ($200): 2025 Mississippi Avenue Wine & Beverage Walk | Wine & Beverage Tasting, Shopping
Get ready to wine a little, laugh a lot, and stroll your way through one of Portland’s most vibrant streets.
2025 Viking Beer Festival @ Nordic Northwest Campus | Beer & Mead, Live Music, Nordic Food, Axe Throwing
Embark on a mesmerizing journey to the heart of Viking heritage at the 2025 Viking Beer Fest!
Sip & Shop @ Hip Chicks Do Wine | Wine Flights, Local Vendors
Join us for an afternoon of wine, shopping, and local creativity at the Sip & Shop event at Hip Chicks Do Wine!
2025 Portland Adult Soapbox Derby | All Ages, Shoebox Derby, Schedule, Photos
As usual the date for our event remains the third Saturday in August which in 2025 is August 16. The event will run from 10a-4p for the public and will be held on Mt. Tabor.
Plant Bingo @ Rae Loft | Win Live Plants, Drinks, Snacks
This isn’t your average bingo – each player enters for a chance at a JUNGLE OF WINNINGS!
Taylor Tomlinson: The Save Me Tour @ Arlene Schnitzer Concert Hall | ‘After Midnight’, ‘Quarter-Life Crisis
A rare talent who has garnered mass appeal at a young age, stand-up comedian Taylor Tomlinson continues to receive praise from fans and critics alike.
OUTRO @ 21ten Theatre | A New Psychedelic Country Musical
Wynn’s off her meds and writing again, but this time it’s a swan song. When she finishes these last songs, her OUTRO, she plans to end her life. But the ghost of her father Stan has other ideas.
McMenamins Edgefield Moveable Feast | Multi-Course Progressive Dinner
A gastronomic adventure awaits… Savor summer at Edgefield’s Moveable Feast!
2025 Art in the Pearl | FREE, 100+ Artists, Craft Demos, Food, Labor Day Weekend
Art In The Pearl has been named one of the top 10 Arts and Crafts Festivals in the country.
CANCELLED: 13 Till Midnight @ Mission Theater | Taylor Swift Tribute
13 Til Midnight takes you on a journey through Taylor’s greatest hits, deep cuts and fan favorites, across eras and albums.
Win Tickets ($40): An Evening w/ Brett Dancer (Baltimore) / Track Mode Recordings @ The Sonder Bar | Deep House, Dance
Originally from Kalamazoo, MI, Brett Dancer began buying records in 1984, and by 1986 was fully immersed in Chicago house music.
Win Tickets ($58): 2025 NW Natural Street of Dreams | Tour 18+ Extraordinary Homes
Spanning four extended weekends (Thursdays–Sundays), the 2025 show features a dynamic mix of luxury, innovation, and housing diversity, reflecting the evolving dream of home.
Win Tickets ($46): Henrik @ Mission Theater | Indie Folk
Henrik is a 23 year old independent folk artist from Salem County, NJ. He’s been writing songs since he was a little kid
Win Tickets ($42): Fred Cole Birthday Celebration w/ Toody Cole, Los Hackals, The Reverberations @ Crystal Ballroom | Garage Rock
We are giving away another pair of tickets to the Fred Cole Birthday Celebration w/ Toody Cole, Los Hackals & The Reverberations @ Crystal Ballroom on August 28. To win, comment below on this post why you’d like to attend. Winner will be drawn and emailed August 25. Join Our Newsletter & WIN Portland Tickets!…
Portland in the News: Who is Dillon, Block Parties, Incoming Emergency Alert & More | August 7, 2025
Have you ever wondered what a pickle does for fun in Portland? Willamette Week asked our favorite fermented friend, Dillon T. Pickle, how he spends his day.
2025 Kenton Street Fair | FREE, 90+ Vendors, Live Music, Local Food
Kenton Street Fair returns for its 13th year on N. Denver Ave in the heart of Downtown Kenton.
Afternoon Garden Teas @ Victorian Belle | Sweet + Savory Bites, Iced + Hot Tea, Wine
The Victorian Belle’s Afternoon Garden Teas are a fun and elegant way to celebrate in August and September!
MANY Portland Weekend Events & Giveaways ($1,300+): Festivals, Concerts, Comedy, Theater, Film, & More!
| Weekend
Win Tickets ($950) Pickathon 2026 @ Pendarvis Farm in Happy Valley, OR | Indie Music Festival
| Uncategorized
Watch 2026 World Cup @ Birdie Time Pub | $2 Rainier & $5 Wings
| events, SE Portland, sports
Happy Hour Sightseeing @ Portland Spirit | Food, Drinks, + River Sailing
| All Ages, Food & Drink
McMenamins Presents 7DS: The Absolute Worst Show: Worst. Vacation. Ever @ White Eagle Saloon | Interactive Open Mic Comedy & Storytelling
| Comedy
Win Tickets ($44) McMenamins Presents Coda (Led Zeppelin Tribute) @ Mission Theater | Rock & Roll
| events, music
Portland in the News: Angry Birds, Sidewalks Sparking Joy, Fleet Week Delays & More | June 4, 2026
| News
2026 White Lotus Summer Market @ Fubonn Shopping Center | FREE, AAPI Food Vendors, Artists & More
| All Ages, events, Food & Drink, Free, music, SE Portland, Shopping
Wine Wednesdays @ Négociant | Weekly Wine Flights & Tastings
| events, Food & Drink, NW Portland
Win Tickets ($81) McMenamins Presents Little Stranger w/ Tropidelic & Jarv @ Crystal Ballroom | Alt Indie Hip-Hop
| downtown, events, music
Win Tickets ($22) McMenamins Presents Decadent 80s Dance Party @ Crystal Ballroom | Portland’s Longest Running 80s Night
| Dance, downtown, events, music
Win Tickets ($81) McMenamins Presents Sondre Lerche @ Mission Theater | Indie Rock
| All Ages, events, music
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