A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
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!
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!
Win Tickets ($20): Desperate Electric w/ Fox Walker @ The Goodfoot | Futuristic R&B
Hailing from the mountains of Montana, Desperate Electric is a blissful matrimony of futuristic R&B and retro dance grooves.
Portland in the News: Netflix & PDX, Spanish Coffee Legacy, Salmon ‘Rest Stop’ & More | July 24, 2025
Feeling extra tired lately? Imagine being a salmon swimming upstream.
2025 Summer Flowers @ Wooden Shoe Tulip Farm | 20 Acres of Blooms, Food, Vendors
Enjoy 20 acres of blooming sunflowers and over 10 different annual and perennial flower varieties.
2025 Brews for the Birds @ Langer’s Entertainment Center | FREE, Beer & Cider, Music, Vendors
Raise a glass to protect the wild! Join us for Brews for the Birds, a two-day outdoor celebration of music, community, and the precious wildlife and wild spaces of the Tualatin River National Wildlife Refuge Complex.
The Dinner Detective in Downtown Portland | Largest Murder Mystery Dinner Show In The U.S.
Are you tired of the same old date nights? Portland’s perfect remedy for entertainment boredom is The Dinner Detective.
Win Tickets ($24): Andy Coe Band’s Jerry Garcia Celebration @ The Goodfoot | Jazz, Blues, Psychedelic
With a rich background in jazz and a joyful enthusiasm for blues and psychedelic rock, Andy Coe is recognized as a deeply intuitive, emotive guitarist
Win Tickets ($40): Sangria Saturday @ Hip Chicks Do Wine | Sangria Specials, Wine Tasting
Join us for an unforgettable Sangria Saturday at Hip Chicks do wine, where we blend the vibrant flavors of summer with our specially crafted sangrias and curated wine flights.
Win Tickets ($114): Demetri Martin: The Quick Draw Tour @ Revolution Hall | Late Show Added!
Known for his unique blend of wit and creativity, Demetri Martin has built a successful career as a stand-up comedian, writer, and director.
Win Tickets ($40): Amplify PDX Block Party @ Open Signal | Live Music, Storytelling, Games & More
Amplify PDX is an unapologetic fundraiser for over 25 local nonprofits at the heart of Portland’s radical spirit.
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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