What to Do in Oregon in May

Learn about UFOs and close encounters in McMinnville, race between breweries in Bend, celebrate Oregon wine in award-winning viticulture regions, and ride a fat-tire bike in Cannon Beach.

By Sam Stites, Katherine Chew Hamilton, Michelle Harris, and Margaret Seiler April 28, 2023

Fat bike riders race down Cannon Beach towards Haystack Rock. 

The April showers have given way., and it's time to take in the May flowers. It's also time to take advantage of longer days and warmer weather with these outdoor gatherings and events. With the run-up to the Rose Festival, the return of many seasonal farmers markets every week, get a jump on summer before school lets out, everyone else gets the travel bug, and things get crowded.

Oregon Wine Month

Throughout may, various wineries and vineyards

Plan a trip to one of Oregon's award-winning viticulture regions to taste great wines in the Columbia River Gorge, Willamette Valley, Rogue Valley, and Portland-metro area. Stop in at Anne Amie Vineyards on Sat, May 6, for Big Red Fest, a celebration of Oregon pinot noir with wines from 16 vineyards; treat mom to a special Mother's Day wine and cheese tasting at Yamhill Valley Vineyards on Sun, May 13; or celebrate Asian-American Pacific Islander Heritage the Oregon AAPI Food & Wine Fest at Stoller Family Estate on Sat, May 20. —SS

Bend Beer Chase

Sat, may 6, 10 barrel brewing, 62950 NE 18th St, Bend

If you enjoy running and you love beer, we've got just the event for you. The Bend Beer Chase is a 12-leg race for teams of six people spanning 55 miles from Bend to Redmond and back. Racers will check in at breweries along the way tasting beers and cataloguing their favorites to have a pint of more than 20 drafts on tap at the finish line in Drake Park. Runners can take part in the subsequent Keg Leg race, a three-mile run/walk through downtown Bend where racers experience eight local breweries along the way. Teams can register online through May 1. —SS

Cannon Beach Fat Bike Festival

Fri–Sun, May 12–14, Cannon Beach

The ATVs of the bicycle world come together annually in Cannon Beach. Their tires, typically at least four inches wide, are designed for riding on sand and snow without sinking in like you might on narrower tires, making the beach the ideal place to show off the fat bike’s terrain-conquering capabilities. Events include a sunset beach ride, a waterfall ride, a scavenger hunt by bike, and a beach bonfire with fat bike races and games. Online registration is $40, and note that if you’re not already a proud owner of a fat bike, you’ll have to borrow or rent your own for this event. —KCH

Florence Rhododendron Festival

Thu–Sun, May 18–21, historic old town florence

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. Celebrating its 116th year, the festival includes food, drink, and crafts from dozens of street vendors, a car show and pancake breakfast, 5k and 10k run, a carnival, and the grand floral parade which will highlight hundreds of rhododendron displays and arrangements. Events take place across the city throughout the weekend, making it the perfect occasion to visit and get to know Florence. Most events are free, but single-day tickets to the carnival start at $30 for presale, and $35 at the gate. —SS

UFO Festival

Fri–Sat, May 19–20, McMenamins Hotel Oregon, 310 NE Evans St, McMinnville 

Founded in 1999, this annual McMenamins-based event celebrates the infamous sighting that took place on May 11, 1950, when Evelyn and Paul Trent apparently spotted a strange flying object hovering near their farm outside of McMinnville. The couple quickly got their camera and managed to capture a couple of snapshots before the mysterious spacecraft floated off. The whole incident resulted in a media frenzy at the time from believers and skeptics alike. But whether you believe all the hype or just enjoy a good alien theme party, it’s nice to know that Oregon is home to the second-largest UFO festival in the entire country (after the one in Roswell, New Mexico). Time-honored shenanigans include an alien costume contest (plus one for pets), a UFO parade, and an alien costume ball. There are also speaker panels with noted UFO experts, live music, and vendor booths where you can purchase all kinds of extraterrestrial memorabilia. Tickets for the entire weekend event are $125, which includes all speaker panels, express entry into presentations, and two drink tokens. —MH

Mt Angel Maifest

3–11 p.m. Fri, 11 a.m.–11 p.m. Sat, 11 a.m.–6 p.m. Sun, May 19–21

Can't wait till Mt Angel goes wild for Oktoberfest in September? The organizers are starting up a spring mini-version, with more than 30 beers on offer from local and international breweries, with German styles like maibock, helles, and dunkel are well represented. The all-ages event features face-painting and other kids' activities, plus live music with plenty of polka.

Reach the Beach

Sat, May 20, starting times and locations vary 

Individual cyclists or teams can choose from different routes, depending on how far you want to ride and how early you want to get up. The hard-core can opt for a 100-mile starting in Tualatin and winding through wine country, while the less ambitious can register for a shorter option and start in Carlton (75 miles), Amity (50), or Grand Ronde (25). The routes all "reach the beach" at Cape Kiwanda in Pacific City in this fundraiser for the American Lung Association. Have a pal pick you up, or get a ticket to be shuttled back to your starting point by bus. —MS 

Upper Clackamas Whitewater Festival

Sat & Sun, May 20 & 21, Carter Bridge day-use area, Clackamas River Highway, Estacada

After a three-year hiatus due to the pandemic and wildfires, the Upper Clackamas Whitewater Festival is back. This whitewater extravaganza takes place between the Fish Creek boat launch and Carter Bridge day-use area. There are more than a dozen races and events throughout the weekend for singles and teams in several different crafts and disciplines, from catarafts and inflatable kayaks to hard-shells and drift boats. Catch the mayhem of the mass-start slalom race where dozens of racers push past each other—sometimes capsizing their competition—as they make their way to the finish line. —SS

Rafters compete in the slalom event at the Upper Clackamas Whitewater Festival. 

Grasslands Barbecue & pFriem Family Brewers Summer Kickoff

Saturday, May 20, 1425 Columbia Gorge Way, Cascade Locks

Grasslands Barbecue (one of Hood River's hottest food trucks) and pFriem Family Brewers (one of Hood River's hottest breweries) are teaming up for a summer kickoff event at the brewery's Barrel & Blending Facility in Cascade Locks. Expect a plethora of smoked meats paired with a wide variety of pFriem beers. There will be multiple sessions throughout the day beginning at 11 a.m., 1:30 p.m., and 4 p.m. with ticketed entry which guarantees tokens for three 16-ounce beer pours, a Grasslands platter including three meats and two sides, and commemorative pint cup. Tickets are not required to attend, but visitors should be warned that Grasslands is known to sell out quickly. 

Vistas del Cielo 

Begins may 27, HIgh Desert Museum, 59800 US 97, Bend

The High Desert Museum in Bend opens a new, original exhibit at the end of May featuring the artwork of Justin Favela. Favela's installation—which translates to "views from the sky"—brings to life the overlooked history and culture of vaqueros (cowboys), braceros (laborers) and traqueros (railroad workers) who worked, roped and ranched throughout the history of the American southwest. The artist uses vibrant piñata paper to tell stories of and pay homage to the familial culture of Latinx Americans whose rich history is intertwined with the high desert region. —SS