Portland's Cinco De Mayo Fiesta takes over Waterfront Park May 1-5. Experience the spirit of Mexico through music, arts, dance, and sport. And let's not forget the food!

Friday kicks off Oregon Wine Month offering special activities and promotions for the enjoyment of Oregon wine.

We have a new Portland holiday and the party to celebrate is in the heart of downtown Sunday. 503 Day Block Party, named after our area code, is a festive way to show love for our city that's on the come up. Celebrating all things Portland at Ankeny Alley. The event is from 1 to 6:03 p.m., exactly five hours and three minutes and is free to attend.

The 19th installment of the Portland Derby is back. Celebrating the greatest two minutes in sports, the “Run for the Rose City,” is the social event of the Spring. A day for fashion, mint juleps, roses, ponies and dancing.

This Sunday The Portland Fire will play their first preseason home game at the MODA Center against the LA Sparks. Then next week the Fire will host the regular season opener on May 9th.

A comedy show for dog lovers? Could it be more Portland? In our city filled with dog stores, dog parks and dog bars, comes a canine-centric sketch show. It’s called Dog People…a Dog Show about People. You can see it live at Kickstand Comedy this Friday. Proceeds go to One Tail At A Time dog rescue.

Congrats to the team at Face Plant! Food & Wine released a list of the top new burger restaurants in the U.S. and the vegan burger hotspot Face Plant came in 5th in the nation. If you’ve never been, it’s in Portland’s Overlook neighborhood and while they are vegan, they take on fast food classics like milkshakes, cheeseburgers, chicken nuggets and fries using recipes from ex-Bon Appétit breakout star Molly Baz. According to Portland Monthly, she and her team spent years developing the shakes.

The annual Walk/Run for the Animals is happening Saturday, on the Vancouver Waterfront. The Humane Society for Southwest Washington's biggest fundraiser of the year will support the local shelters efforts to help dogs, cats and other pets in need get the care they need to be ready for adoption.

Crafty Wonderland is going down at The Oregon Convention Center. Portland jewelry artists Torie Nguyen and Cathy Zwicker were tired of craft fairs and holiday markets getting rained out, so they created Crafty Wonderland, an indoor marketplace to support PDX makers and artists.

Also at the Convention Center: The annual Bricks Cascade, Portland’s premier public LEGO event. See creations from hundreds of builders from the Pacific Northwest and worldwide in this two-day event.

Join Lan Su in partnership with more than 20 local cultural organizations, performers, and artists to celebrate Asian American, Native Hawaiian, and Pacific Islander (AANHPI) Heritage Month.

Candlelight concerts bringing the magic of a live, multisensory musical experience to The Old Church Concert Hall like The 90's Unplugged and Coldplay & Imagine Dragons.

PLANNING AHEAD

Doggie Dash 2026 Saturday May 9 at 7:30. Bring your pup to Waterfront Park for Oregon Humane's biggest fundraiser of the year! There will be animal-loving local businesses, food trucks, dog agility course, family-friendly activities, a Libation Station for 21+, live music, and contests for you and your pup! Make sure you stop by the Photo Booth for a keepsake pic. Dashers who fundraised $500+ can enjoy complimentary treats in the VIP Tent, including goodies and perks!

The $30 Live Nation “Summer of Live” ticket special is now on. There are several local shows included, like Alex Warren on June 12, 5 Seconds of Summer on June 30, and comedian Matt Rife on October 10. All three shows are at the Moda Center. Get ‘em now at Live Nation dot com.

Kurt Russel will be back in Portland May 9 for The Hollywood Theater’s 100th anniversary and a showing of his 80’s scifi horror flick The Thing. The Hollywood will show a a 35mm presentation of “The Thing,” followed by a live onstage Q&A with Russell.

Stacey & Mike's Helping Hands are big fans of the local nonprofit Stone Soup PDX and they've got a fun event coming up May 16th. Jam Jam brings together jam bands + jam making at Midtown Beer Garden in support of Stone Soup PDX’s culinary training program.

The Pink! Rosé Festival returns May 17 at the Hillsboro Ballpark to sip, savor and explore spring releases from 28 Tualatin Valley Wineries, including rosés, whites and orange wines. 50+ wines to taste! Text your girls, get your tickets and make your plans. Stacey and her besties will see you there!

#BloomTourPDX is coming back for year 3, May 21-June 8! This is one of the most beautiful ways to spend an afternoon in Portland. Walking, connecting and of course getting pictures for the gram of inspiring unique floral installations around town. If you're a florist or venue who would like to take part it's not too late to sign up. They need sponsors too.

McMenamins’ UFO Fest prepares to land in McMinnville, OR, on May 15-16. Home to the site of the famous 1950 Trent UFO sighting, this fest goes beyond just costumes and Alienator IPAs. It's where credible science, firsthand accounts and culture collide

The Bloody Mary Festival returns to Portland for its 8th annual event at the Redd on Salmon May 30. Top Portland bars, restaurants and artisanal bottled mixes will vie for the title of "Best Bloody Mary in Portland." An expert panel of judges will determine the ultimate Bloody Mary in Portland, but attendees will be able to vote and crown the "People's Choice Award" for best in Portland.

Portland International Raceway will bring IndyCar drivers back to Portland International Raceway for high‑speed competition August 7–9, 2026. Tix on sale now!

STACEY & MIKE WATCHLIST

The Devil Wears Prada 2 hits theaters this weekend. And the OG cast is back; Meryl Streep, Anne Hathaway, Emily Blunt & Stanley Tucci. Did you know Emily and Stanley are related? Stanley married Emily’s older sister, Felicity Blunt, in 2012, after meeting at Emily’s wedding to John Krasinski in 2010.

*DWP2 Starbucks Secret Menu: Four drinks modeled after the film’s characters; Miranda’s ultra-demanding custom latte that she needs on her desk promptly at 3pm! Andy’s slightly sweet, evolving cappuccino. Nigel’s go-to doppio and Emily’s iced chai. The drinks launched this week in the Starbucks app.

*If you're seeing DWP2 at an AMC theater make sure to get popcorn but make it stylish. Grab your red, top-handled, luxury-inspired popcorn handbag. Also hitting AMC snack bars this Friday, for the 25th anniversary of Shrek, a popcorn bucket shaped like Shrek’s outhouse. Shrek 5 is in production now and will hit theaters Jun 30, 2027

The 152nd Kentucky Derby will be held on Saturday at Churchill Downs in Louisville, KY. The marquee race, known as the "Run for the Roses," is scheduled to have a post time of approximately 3:57 p.m. PT.

STACEY: Criminal Record and Your Friends & Neighbors. If you have one you're loving please share because I'm just over here waiting all week for new episodes. ugh, I cannot be bothered.

MIKE: Your Friends and Neighbors, Apple TV. A new season just started!

Madison