Oregon makes great wine. And during the month of May, wineries and vineyards across the state—in the Columbia River Gorge, the Willamette Valley, the Rogue Valley, and within Portland—put on special dinners and tastings to celebrate that fact. Also on deck: live music, free winery tours, wine-and-dumpling pairings, and much more.

This spring, the Schreiner family marks 101 years of breeding and selling new iris varieties. Stroll the 10-acre display garden to see some of the farm's most eye-catching iris varieties, planted alongside a spectacular mix of companion plants. Weekends bring food vendors and wine tastings, and there's a family day on May 17, golden-hour events on several Thursday evenings, and an artist fair over Memorial Day. Daily entry is $6–15, or $38 for a season pass; children under 12 are free.

Do you enjoy running? What about beer? The Bend Beer Chase is a 12-leg race for teams of up to six people spanning 57 miles from Bend to Redmond and back. Racers check in at breweries along the way, tasting beers and cataloging their favorites before choosing from 20 taps for a full pint at the finish line in Drake Park. Teams can register online before the event; fee varies depending on team size.

With more than 60 ciders on tap from 30 makers in Oregon and Washington—plus a variety of food and craft vendors—both seasoned and starter sippers are sure to find something that suits. Held at the Western Antique Aeroplane and Automobile Museum, the all-ages event is free to attend, but anyone age 21 and up planning to taste will need need a $35 ticket ($40 day-of).

What, you may ask, might you find on display at the Northwest's largest Lego convention? While we don't know exactly what's planned this year, we do know that the theme is Piece on Earth and that past displays have included eight-foot-tall replicas of Multnomah Falls, so we suspect it'll be epic. Expect hundreds of Lego creations, lots of interactive opportunities and contests, and a variety of vendors. Single-day tickets to the public exposition are $17. A private convention, limited to those who are registered as Adult Fans of Lego (a thing), runs April 30–May 3.

Portland's new WNBA team embraces its area code with a fan fest outside the Moda Center before a preseason game against the Los Angeles Sparks at 4pm. Expect mini games, half-court shoot-arounds, a pop-up skateboard park, and jersey customization and sign-making stations. 

This weeklong gathering in Oregon's so-called Outback began in 2023 as a way to share traditional skills and crafts—think blacksmithing, hide tanning, tracking and trapping, felting, plant dyeing, and basketry. Registration is $290 for adults, and there are numerous camping options.

On May 11, 1950, in the sleepy outskirts of McMinnville, Evelyn Trent's eye caught a glimmer of light in the sky: a metallic disc, soundlessly soaring toward her house. She yelled for her husband, Paul, who, after seeing it for himself, ran back inside to grab the Kodak. He snapped two pictures before the object flew off, leading to a media frenzy—and, in 1999, to the founding of what's now the country's second largest UFO festival (after the one in Roswell, New Mexico). Time-honored shenanigans include an alien costume contest (and one for pets), alien costume ball, and parade—plus panel conversations, live music, and vendors hawking all sorts of extraterrestrial memorabilia. Much of the fest is free, but some events require tickets.

The Florence Rhododendron Festival is one of the oldest flower festivals on the West Coast, younger only than Portland's Rose Festival and Pasadena's Tournament of Roses. Now in its 119th year, the fest includes dozens of food and crafts vendors, a 5k run, a carnival, a car show, and a culminating parade highlighting hundreds of rhododendron displays and arrangements. Most Rhody Days events are free, but all-day ride passes to the carnival are $30 in advance, $35 at the gate.

The ATVs of the bicycle world come together annually in Cannon Beach. Fat bike tires are usually four to five inches wide and are less likely to sink into sand than skinny rubber, making the beach an ideal place to show off the vehicle's terrain-conquering capabilities. Events include a sunset beach ride, a waterfall ride, and a beach party with fat bike races and games. Online registration is $45, and note that if you’re not already a proud owner of a fat bike, you’ll have to borrow or rent your own.

The whitewater extravaganza returns with more than a dozen races and events for singles and teams. Expect numerous crafts and disciplines, from catarafts and inflatable kayaks to canoes and paddleboards. Catch the Clack Fest mayhem of the mass-start slalom race, in which dozens of racers push past each other—sometimes capsizing their competition—as they make their way to the finish line.

This American Lung Association fundraiser starts in the metro area and ends at the coast; individual cyclists or teams can choose between different routes and starting times. The hard-core can opt for a 100-miler starting at Scappoose High, while the less ambitious can register for a shorter option and start in Vernonia (77 miles), Jewell (43), or Olney (24). The routes all "reach the beach" at Fort Stevens State Park. Have a pal pick you up, or get a ticket to be shuttled back to your starting point by bus. The minimum fundraising requirement is $200 per person.