THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!

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A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!

Portland Spirit Brews on Board | Taste Beers & Ciders from 12+ Local Breweries

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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

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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

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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

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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

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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

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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

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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

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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 

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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.

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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

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Join us for a fun afternoon of play! In this workshop we will dip our toes into Deep End’s unique improv style.

THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!

A round up of what's going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!

Scooped Ice Cream Festival @ Esther Short Park in Vancouver, WA | 50+ Flavors of All You Can Eat Ice Cream

July 18-19 - The Pacific Northwest's premier ice cream festival is back at Esther Short Park in Vancouver, WA for two all-you-can-eat days of scoops, live music, and summer fun. Scooped! returns July 18 and 19, 2026, 11:00 AM to 7:00 PM — and your ticket includes unlimited ice cream from 50+ flavors served up across Scoop Valley.

Chamber Music Northwest presents CONFLUENCE: Our Shared Voices 2026 Summer Festival | 70 of the world and our region’s finest chamber musicians!

Music has the ability to connect us beyond words, labels, and borders, inviting us to celebrate both our differences and our common ground.

Tea Fest PDX @ World Forestry Center | A Celebration of Tea Culture

June 27 - TeaFestPDX is more than a festival, it’s a community.

St. Helens Independence Day Celebration 2026 @ Columbia View Park | Music, Food, and Activities for All Ages

July 4 - Celebrate the Fourth of July at Columbia View Park in St. Helens, Oregon – one of the most scenic Independence Day destinations in the Pacific Northwest.

Win Tickets ($160): 2027 Portland Folk Festival @ Crystal Ballroom | 30+ Local & National Artists

January 30 - An annual celebration of folk and Americana music showcasing 30 local and national artists hosted by the historic Crystal Ballroom.

Win Tickets ($86): McMenamins Presents Madison Ryann Ward @ Mission Theater | Contemporary Christian, Pop + R&B

September 4 - Faith-based singer/songwriter Madison Ryann Ward writes warmhearted songs that mix mature pop and contemporary R&B with accents of gospel, blues, and folk.

Win Tickets ($70): McMenamins Presents “A Hot August Night” with Super Diamond @ McMenamins Grand Lodge in Forest Grove | The Neil Diamond Tribute

August 22 - An uncanny tribute to beloved master singer/songwriter/performer, American pop icon Neil Diamond – Super Diamond has appeared on The Late Show with David Letterman, CNN, VH1, Fox News, and Comedy Central, and has been featured in publications such as Rolling Stone Magazine, The New York Times, and the San Francisco Chronicle.

Portland in the News: Waterfront Restaurant, Airport Accolades, Heatwave & More | June 11, 2026

The Portland Spirit has big plans to open a new restaurant in the former Rose Festival headquarters in Tom McCall Waterfront Park. 

McMinnville Art Festival @ Downtown McMinnville | 50+ Artists & Artisans, Interactive Kids’ Crafting, Art Demos, & More

July 18-19 - Celebrate creativity in the heart of Oregon wine country at the McMinnville Art Festival, a free two-day outdoor event showcasing the work of talented artists and artisans from across the region.

PRIDE at the Museum @ OMSI | A night at the museum celebrating the LGBTQ+ Community

June 12 - Celebrate PRIDE at the Museum with an evening of science, community, and joyful exploration!

Villain Arts Tattoo Festival @ The Rose Quarter | Celebrate the Art of Tattooing

July 17-19 - Tattooing is more than body art—it’s a global language of identity, resilience, and self-expression.

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