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!

Roses & Rosé @ Portland Rose Garden | Wine Tastings, Charcuterie, Garden Tour

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Join us for an unforgettable evening at one of Portland’s most iconic and fragrant landmarks — the Portland Rose Garden!

Win Tickets ($30): Scott Law Band @ The Goodfoot | Rock, Jazz, Blues, Folk

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Scott Law is a guitarist, singer and songwriter dedicating his life to music through live performance, improvisation and his own compositions.

Win Tickers ($112): Leo Kottke @ Aladdin Theater | Blues, Jazz, Folk

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Acoustic guitarist Leo Kottke was born in Athens, Georgia, but left town after a year and a half.

Win Tickets ($100): Macy Gray: On How Life Is 25th Anniversary Tour @ Crystal Ballroom | R&B + Soul

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The ability to compose refreshingly candid music that resonates deeply with listeners isa rarity in music. Few artists possess this tool, however, R&B/soul singer-songwriter, musician, and record producer, Macy Gray, is one of them.

Dock Party – Fire Edition @ SE Industrial District | Live Fire Cooking, Cold Drinks, Award-Winning Chefs

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The Live Fire Cooking Club turns all the way up at the Dock Party!

Portland in the News: James Beard Winners, No Off-Leash, Portland Fire & More | June 19, 2025

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No more free-wheeling for Fido. OregonLive reports park rangers can now issue a ticket for off-leash dogs in undesignated areas without first issuing a warning. 

Midsommar-ket & VHS Swap @ Dots Cafe | Local Vendors, Wicker Man Burning, DJ Drokker

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We are bringing the swap and market back for a little Midsommar session. Gonna have a fun one in store and even burn a little Wicker Man after the sun goes down, for the harvest of course.

Win Tickets ($152): Jonathan Richman feat. Tommy Larkin on drums @ Aladdin Theater | Frontman of Modern Lovers, Proto-Punk

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Buy tickets early. Buy tickets often. This is just good general life advice, but even more so when you’re talking about Jonathan Richman

7 Wonders of the Gorge @ Portland Spirit | Jet Boat Cruise, Majestic Views

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Experience some of the most majestic views of the lower Columbia River Gorge visible by water aboard the Explorer Jetboat!

Haute & Hip @ Club Privata | Portland’s #1 Lifestyle Club

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Step into the spotlight at Haute & Hip, where cutting-edge fashion meets the hottest beats.

Win Tickets ($400): 2025 Project Pabst @ Tom McCall Waterfront Park | Iggy Pop, Devo, Death Cab for Cutie, Japanese Breakfast & More

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Project Pabst, the beloved music festival brought to you by Pabst Blue Ribbon and independent promoter True West, is thrilled to announce the lineup for its 2025 edition.

Free Improv Workshop @ Deep End Theater | Fun Afternoon of Play

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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.

Win Tickets ($10): Farnell Newton & The Othership Connection @ The Goodfoot | Jazz, Latin, Soul, Funk

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Trumpeter Farnell Newton is one of the most versatile musicians and educators in the Northwest, seamlessly blending straight-ahead jazz, smooth jazz, Latin music, soul, hip-hop, funk and more.

2025 World Beat Festival – Turtle Island @ Salem Riverfront Park | Music, Dancing, Food

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This year we are celebrating Turtle Island; the indigenous peoples of North and South America!

Win Tickets ($20): Wicked Craft Solstice Night Market @ Rae Loft | Women & Femme-Owned Vendors, Happy Hour

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Wicked Craft: Bazaar and Craft Fairs are a woman and femme business owned craft fair & market series operated by Rae Loft at the Bakery Building.

Portland Gay Men’s Chorus Presents ICONS: Pride Goes Pop @ Arlene Schnitzer Concert Hall | Songs by Sia, Sam Smith, Chappell Roan & More

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The Portland Gay Men’s Chorus (PGMC) is turning up the volume on Pride Month with ICONS: Pride Goes Pop, a one-night-only concert experience.

Portland in the News: Free AC, Pride, Scenic Views & More | June 12, 2025

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USA Today has chosen several locations in Oregon as the country’s most scenic viewpoints, including our beloved Crater Lake. 

Campfire Tales: Live Storytelling @ Echo Theater | Pre-Show Workshop, S’Mores

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Campfire Tales presents an evening of live, true storytelling. This Portland-based series fosters community through personal narratives.

2025 Portland Spirit Bigfoot Adventure Cruises | Learn the History of Bigfoot on a Jetboat

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On this Columbia River boat tour, you’ll explore the history and lore of Bigfoot while traveling 80 miles roundtrip on a high-speed jetboat from Portland to Multnomah Falls.

2025 Oregon Midsummer Festival @ Nordic Northwest | Flower Crowns, Music, Shopping & More

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Decorate the Midsummer pole and make flower crowns, watch live music and performers, indulge in Nordic summer delicacies, play games and make crafts, shop vendors and enjoy – this is Midsummer!

2025 Portland Father’s Day Brunch & Dinner @ EastBurn | Food Specials

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Toast dad at EastBurn all day on Father’s Day!

Pineapple Party @ Club Privata | Portland’s Premiere Lifestyle Club

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Now that summer has begun, it’s time for our third annual Privata Pineapple Party.

Over the Rainbow Portland Pride Kickoff Party @ Darcelle XV Showplace | Drag Performances, VIP Meet & Greet

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Come celebrate Portland Pride Month Kick-Off at Darcelle XV Showplace!

2025 Oregon Renaissance Faire @ Clackamas County Fairgrounds | Marketplace, Food, Drinks, Entertainment

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Step into the magic of the Oregon Renaissance Faire, returning for four enchanting weekends in June 2025!

Win Tickets ($20): Wrath of Kahn w/ Brothers Jam @ The Goodfoot | Jerry Garcia Band Music

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Wrath of Kahn brings the Jerry Garcia Band vibe from beyond the final frontier.

My First Rodeo + Juneteenth Rodeo Afterparty | Portland Juneteenth Celebration, Photoshoot, Brunch, Drinks & More

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Celebrate Juneteenth with us at a Western-themed brunch, photoshoot, and style-forward experience you won’t forget.

Win Tickets ($240): 2025 Portland Horror Film Festival | 70+ Short & Feature Films

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Portland Horror Film Festival returns to the historic Hollywood Theatre and Clinton Street Theater June 11-15th for its 10th annual event!

Win Tickets ($26): Plant Bingo @ Rae Loft | Win Plants, Snacks, Drinks

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Join us for a one-of-a-kind botanical Bingo Night where luck meets leaves, and you could take home a brand-new plant friend!

Win Tickets ($56): Constant Debauchery w/ Major Tomboys @ Mission Theater | Depeche Mode & David Bowie Cover Bands

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Constant Debauchery is the Pacific Northwest’s premier Depeche Mode celebration band, playing the arena hits, club faves, and b-sides of the dark dance music pioneers.

Portland in the News: Aurora Borealis, James Beard Public Market, Day Trippin’ & More | June 5, 2025

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Residents of Northern Oregon and Southwest Washington were treated to a light show Sunday night courtesy of the Aurora Borealis according to KATU.

Win Tickets ($140): 2026 Portland’s Folk Festival @ Crystal Ballroom | 30+ Local & National Artists

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An annual celebration of folk and Americana music showcasing 30 local and national artists hosted by the historic Crystal Ballroom with all proceeds donated to Sunstone Way.

2025 Rosewood Saturday Celebrations | Handmade Goods, Food, Music & More

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Rosewood Saturday Celebrations, The Rosewood Initiative’s annual summer market, is back! 

A Night With Ghost Tour: Haunted Adventure in NW Portland | Friday The 13th

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Explore Portland’s haunted past on this spine-chilling strolling tour through Slabtown and Nob Hill.

2025 Rose City Book & Paper Fair @ DoubleTree by Hilton | Used, Rare & Collectible Books

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Our local and traveling booksellers share your passion for books, and will be presenting their most interesting material

Sip & Shop @ Hip Chicks Do Wine | Wine Tasting, 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 Father’s Day Cruises @ Portland Spirit | Brunch BBQ Buffet + Dinner Cruise

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Give Dad an unforgettable Father’s Day with a special two-hour cruise on the Willamette River.

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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