A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!
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!…
Win Tickets ($77): Floater @ Crystal Ballroom | Rock Band
Floater is an American rock band currently based in Portland, Oregon
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!
Win Tickets ($250): 2025 Circle V Portland @ Castaway Portland | 20+ Restaurants, Craft Beverages, Vendors
Circle V Portland is back for its second year! Join us for a one-of-a-kind tasting extravaganza celebrating our city’s delicious plant-based food and drink scene.
2025 Jade International Night Market @ PCC Southeast Campus | FREE, Food & Retail Vendors, Live Entertainment
The Jade International Night Market, organized by APANO, is a vibrant, free annual celebration of the diversity and multicultural communities that make up the Jade District and East Portland.
Roller Derby Global Championship Rematch @ The Hangar | Rose City Rollers vs Arch Rival from St. Louis
Portland’s reigning World Champions, the Rose City Rollers, take on Arch Rival from St. Louis on 8/23!
2025 Sunflower Festival @ Bella Organic | 5 Acres U-Pick, Food, Wine, Farm Animals
Bella Organic Farm’s Sunflower Festival is officially open from August 8th every day until September 7th, 2025!
2025 NW Natural Street of Dreams | Tour 18+ Extraordinary Homes
The NW Natural Street of Dreams®—a signature summer event produced by the Home Building Association of Greater Portland (HBA)—returns July 31–August 24, 2025.
Ladies Night Out @ Club Privata | Portland’s Premiere Lifestyle Club
Dress to impress and step into a world where the men perform for you. Get prepared for us to bring you a show from 8-10pm full of seductive male dancers.
Wine Wednesdays @ Négociant | Weekly Wine Flights & Tastings
Wine Wednesday is now in its third year and has become a staple in our weekly routine and part of the tradition around here.
Win Tickets ($56): Iron Maiden vs Metallica @ Crystal Ballroom | Feat. Fear of the Dark & Battery, Inc.
Prepare to be transported to the hallowed grounds of Rock & Metal as Fear Of The Dark unleashes a sonic assault of Iron Maiden anthems.
FREE Improv Workshop @ Deep End Theater | Lead 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.
Win Tickets ($102): The Living Tombstone @ Roseland Theater | Electronic Duo
The Living Tombstone is a musical project founded by Yoav Landau in 2011, initially as a YouTube channel and solo venture.
Portland in the News: From ‘Ghost Mall’ to Startup Hub, Paddleboards vs Blackberries, Places of Pride & More | July 31, 2025
A new exhibit at the Architectural Heritage Center honors Portland spaces that were safe havens for the LGBTQ+ community.
The People’s Courts Pickle Ball Destination | Premium Food & Beverage, Ping Pong, Bocce Ball & More
The People’s Courts is Portland’s premier pickleball event destination hosting corporate parties, teambuilders, wedding parties, birthdays, and more!
2025 Vancouver Wine & Jazz Festival @ Esther Short Park in Vancouver WA | 18 Bands, 70 Wines, 20 Artists & Crafters
The 2025 Festival features nationally acclaimed jazz, blues, and gospel bands.
Win Tickets ($80): Forest Pub @ Mission Theater | Wildfire & Wine – from Vineyard to Palate
Join us for an evening of insight and conversation as we dive into the complex and sensitive relationship between wildfire and wine.
Frosé Fridays @ Hip Chicks Do Wine | New Wine Slushy Every Week
Kick off the weekend and beat the heat with a Wine Slushie and delicious seasonal small plates!
Naughty Negligee @ Club Privata | Portland’s Premiere Lifestyle Club
What a way to get the weekend started and get some relief from a busy work week.
2025 August Fruit Loop Events in Hood River & Parkdale | U-Pick Peaches, Sunflowers, Pickle Festival & More
Experience U-Pick Peaches, Sunflowers, Pickle Festival & More at the Hood River Fruit Loop this August!
Last Thursday Art Opening @ The Goodfoot | Featuring Kyle Allen, Lea Barozzi & Nic Vik
This months feature artists are Kyle Allen, Lea Barozzi & Nic Vik. Along with music selected by DJ Welly Well
Win Tickets ($40): Dennis McNally @ Bagdad Theater | Grateful Dead Biographer & Publicist
Dennis McNally is the Grateful Dead’s authorized biographer and longtime publicist.
Win Tickets ($132): The Swell Season w/ Glen Hansard & Marketa Irglová @ Arlene Schnitzer Concert Hall | Folk-Rock
After reconvening for a limited number of sold-out shows in March 2022, followed by a more extensive US tour in August 2023, the duo returns with new music.
Win Tickets ($22): Decadent 80s Dance Party w/ DJ NoN @ Crystal Ballroom | Portland’s Longest Running 80s Night
Get ready for a fun night of dancing to all your favorite hits and requests from the 1980s!
THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!
| Today
2026 Swan Island Dahlia Festival | 50 Acres of Blooms, Food Carts, Live Music
| All Ages, events, Food & Drink, music
7 Deadly Sins Pants On Fire Family Friendly Show @ White Eagle Saloon | Seven True Tales, One Lie
| All Ages, Comedy, north portland, theater
Win Tickets ($130): Portland Weird Fest @ Oaks Park | 60+ Vendors, Rides, Live Bands, Costume Contest & More
| All Ages, Food & Drink, music, SE Portland, Shopping
Win Tickets ($136): Dogstar w/ The Backfires @ Crystal Ballroom | Keanu Reeves, Alt-Rock
| All Ages, downtown, events, music
Win Tickets ($92): Marc Price @ Mission Theater | Comedy, Star of ‘Trick or Treat’, ‘Family Ties’
| Comedy, NW Portland
Win Tickets ($22): Decadent 80s w/ DJ NoN @ Crystal Ballroom | Portland’s Longest Running 80s Night
| downtown, events, music
2026 Cannon Beach Cottage Tour | Self-Guided Walking Tour of Beautiful Homes, Opening Night Bash
| All Ages, events, Visual Art
2026 Time-Based Art Festival @ Portland Institute for Contemporary Art | Experimental Performances, Live Music, Dance & More
| Dance, events, Film, Food & Drink, music, NE Portland, theater, Visual Art
Lake Oswego Clean Energy and EV Fair @ Lake Oswego United Methodist Church | Test Drive EVs, Learn About Solar, Batteries & More
| All Ages, events, Home Show, Services, Shopping
Win Tickets ($42): Valkerie w/ Withholden, Laughing About Nothing, Fawkes Glove @ Mission Theater | Alternative Rock
| All Ages, music, NW Portland
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