A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!
2026 Art in the Pearl @ North Park Blocks | FREE, Art, Artists, Craft Demos and More
September 5-7 – Over one hundred artists show and sell work ranging from fine wooden furniture to beautiful paintings to photography, glass, clay, metal, jewelry, and much more!
Portland Fire vs. Seattle Storm Watch Party w/ Backcourt Collective @ The People’s Courts | Free, Dinner, Drinks
August 14 – Join Backcourt Collective at The People’s Courts this Friday, August 14 to watch the Portland Fire take on Seattle Storm at 7pm!
2026 Jade International Night Market @ PCC Southeast Campus | FREE, Food & Retail Vendors, Live Entertainment
August 29 – 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.
2026 Hawthorne Street Fair in SE Portland | Local Vendors, Live Music, Food & Drink
August 23 – This beloved neighborhood tradition draws over 23,000 visitors in a single day, making it one of the largest street fairs in the state.
Debut of Shanrock’s Triviology @ The Goodfoot | Full Bar & Food Menu
August 16 – The Goodfoot is filling out its vibrant series of music and other fun flings by hosting our pub quizzery!
2026 Halloween Boo Cruise @ Portland Spirit | DJs, Costume Contest, Food & Drinks
October 31 – Get on board for a ghoulishly good time on our Halloween Boo Cruise!
2026 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 2026 is August 15. The event will run from 10a-4p for the public and will be held on Mt. Tabor.
Bend Beer Run @ The Commons in Bend, OR | Scenic 5k, Four Craft Beer Stops, Costume Contest
August 29 – The Bend Beer Run is a fun, untimed 5K through downtown Bend and along the Deschutes River featuring four craft beer stops along the course.
2026 Kenton Street Fair in North Portland | Live Music, 100 Vendors, Food Carts
August 16 – Over 100 vendors, two live music stages and a great food court. Family friendly, free and a lot of fun!
Ron Tonkin Gran Tourismo Presents Harmony in the Desert @ Tetherow Resort | A Benefit Concert for Music Education
August 27 – “Harmony” is coming to Bend, Oregon this August.
50% Off Mystery & Suspense @ Rose City Reads | Flash Sale
August 14-15 – Come restock on all your favorite who done its!
The Last Woody: A Final Toast @ Deschutes Historical Museum in Bend, OR | Craft Brewers & Distilleries, Live Music, Lawn Games, Delicious Food
August 29 – After years of unforgettable pours, live music, and gnome-filled fun, 2026 marks the last-ever Little Woody.
Win Tickets ($48): McMenamins Presents Tōth @ Mission Theater | Indie Pop
October 24 – Brooklyn-based songwriter and multi-instrumentalist Tōth (Alex Toth of Rubblebucket) returns with his third album, And The Voice Said.
Theater in the Park presents ‘The Producers’ + Children’s Matinee of ‘Winnie-The-Pooh’ @ Drake Park in Bend, OR | Mel Brook’s Outrageous Musical Comedy
August 14-15 – Experience an unforgettable summer evening under the stars as Theater in the Park returns to Drake Park with Mel Brooks’ outrageous Broadway hit, The Producers.
Spooky Boys, Waves Crashing & Bridal Veil @ The 6 Below Midnight | Indie-Surf, Shoegaze, Dreampop
August 15 – A night of shoegaze, surfy indie rock, and ethereal dreampop with Spooky Boys, Waves Crashing and Bridal Veil.
Win Tickets ($250): Circle V Portland @ Castaway | Unforgettable Plant-Based Tasting Experience, Fundraiser
September 20 – Join us on Sunday, September 20 at Castaway for a one-of-a-kind walkaround tasting experience featuring creative and oftentimes unexpected chef collaborations, tasty bites from craft food makers, and sips from a dozen beverage producers.
Portland in the News: Trash Art, Lost & Found, Petroglyphs & More | August 6, 2026
If you drop your phone, keys, wallet or watch into a public trashcan in Portland, do not fret. There’s a hotline for that.
Future Fest @ Portland State University | FREE Youth Event, Live Art, Music, Workshops & More
August 15 – What will Greater Portland look like in 2077? The answer starts with youth.
Watch Football Games @ Birdie Time Pub | $2 Beers, Food Specials, Ducks, Seahawks
Enjoy $2 beers and food specials during game time!
Plant Bingo @ Hip Chicks Do Wine | Beautiful Plant Prizes, Wine, Snacks
August 16 – Get ready for a fabulous afternoon of wine, plants, and plenty of sass!
PFCAT Creator Expo @ OMSI | FREE, Meet Local Creative Orgs & Collectives
August 22 – The event brings together filmmakers, animators, students, and working creatives for a day focused on creativity and connection.
Win Tickets ($56): Constant Debauchery w/ Kiss Me Kiss Me Kiss Me, West End Entertainment District @ Mission Theater | Depeche Mode Tribute, Cure Tribute
October 2 – Constant Debauchery is the Pacific Northwest’s premier Depeche Mode celebration band.
Chaotic Singles Game Night @ Moxy Portland Downtown | Play Games, Drink Specials, Meet Your Match
August 7 – Single? Tired of the apps? Come party!!
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 ($44) McMenamins Presents Coda (Led Zeppelin Tribute) @ Mission Theater | Rock & Roll
CODA is a Seattle-based Led Zeppelin tribute super group with a cast of 6 world class musicians.
Win Tickets ($70): McMenamins Presents Kyle Gordon @ Mission Theater | Pop & Comedy
October 28 – Kyle Gordon’s History of Music is the best concert AND the best comedy show anyone ever did before all rolled into one as well.
The 26th Annual Portland Erotic Ball @ Crystal Ballroom | 21+, Hosted by Sasha Scarlett, Live Music, Burlesque, Costume Contest, & More
October 31 – Portland Erotic Ball, one of the city’s most iconic and enduring Halloween traditions, returns for its 26th anniversary this fall with a bold new vision while continuing its legacy as Portland’s largest adult Halloween event.
2026 Sunflower Festival & U-Cut @ Bella Organic on Sauvie Island | Farm Store, Wine & Cider, Cow Train Rides & More
August 8 – September 14 – A sunflower field and U-Cut is a magical way to incorporate our love for flowers into a beautiful event!
Win Tickets ($24): 2026 Portland Festival of Cinema, Animation & Technology @ OMSI | 170 Films, Matthew Inman of The Oatmeal, Festival Parties & More
August 18-23 – Films include live action features, animation for kids, animation for adults, sci-fi, comedies and documentaries.
2026 Silobration NW @ Abbey Road Farm | Wine, Local Food, Live Music, Market, 5k & More
August 15-16- Celebrate the summer’s final days and the start of harvest season at Silobration NW.
Win Tickets ($81) McMenamins Presents Little Stranger w/ Tropidelic & Jarv @ Crystal Ballroom | Alt Indie Hip-Hop
Hailing from Philadelphia and now based in the vibrant city of Charleston, SC, alt indie hip-hop duo Little Stranger (Kevin and John Shields, no relation but best friends) have spent years honing their signature sound and perfecting their version of the ‘organized chaos’ that a Little Stranger live show entails.
Win Tickets ($81) McMenamins Presents Sondre Lerche @ Mission Theater | Indie Rock
Sondre Lerche has always been a romantic.
Kumoricon 2026 @ Oregon Convention Center | Anime & Japanese Culture Convention
Celebrating more than twenty years of anime and Japanese culture, Kumoricon is back for its biggest year yet!
MANY Labor Day Weekend Events & Giveaways ($2,200+): Festivals, Concerts, Comedy, Theater, Film, & More!
A round up of what’s going on in Portland this weekend including live music, concerts, comedy, trivia, happy hours, movies & more!
MADE Bike Show @ Zidell Yards | Handmade, One-of-a-Kind Bikes, New Products
August 21-23 – MADE Bike Show is a celebration of handmade bicycles, independent builders, and the people shaping the future of cycling.
Win Tickets ($40): GossNight @ The Siren Theater | Live Game of Telephone
August 30 – GossNight is Portland’s wildly entertaining live game of telephone, where one true story is passed between seven performers until it returns completely transformed.
THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!
| Today
7 Deadly Sins Pants on Fire Freaky/Filthy Late Show @ The White Eagle Saloon | 7 True Tales, One Lie
| Comedy, events, north portland, theater
Win Tickets ($22): 2026 Corn Maze ‘5 Kind Acts’ + Pumpkin Patch @ Bella Organic Farm on Sauvie Island | Apple Cider, Trains, Petting Zoo & More
| All Ages, events, Food & Drink, Halloween, NW Portland, Visual Art
Win Tickets ($80): Haunted Corn Maze @ Bella Organic Farm on Sauvie Island | Ghouls, Zombies, Costume Party
| All Ages, events, Food & Drink, Halloween, NW Portland, theater
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
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