May Events

The Portland Flea + Food is a monthly market held on the last Sunday of the month in Portland, Oregon. Every market features 80+ local artists, makers, and curators of the best vintage, handmade and locally-sourced goods in town.

Shop for handmade crafts, snack on traditional recipes and enjoy entertainment straight from Guadalajara at this popular Cinco de Mayo festival.

Portland’s biannual art and craft fair boasts unique handmade wares from 225+ local vendors.

Held the day before Mother’s Day, the Camas Plant and Garden Fair draws in thousands of people to enjoy and explore an amazing selection of plants, trees, garden art and supplies, and much more provided by local growers and vendors. Kids’ activities, live music, entertainment, fresh food, and the shops and restaurants of Downtown Camas…

The St. Johns Bizarre is a uniquely crafted celebration that kicks off the summer street fair season in Portland with music, kids’ activities and more. Held annually on the second Saturday in May, the Bizarre brings music, crafts and food to the crowds attending the St. Johns Parade. After the parade, the entire six block…

Come and view gorgeous flowers at their peak bloom time, then pick bouquets for all the special moms in your life at this annual show and marketplace. All proceeds benefit Crystal Springs Rhododendron Garden.

Every May, thousands of visitors flock to the city’s famous UFO Festival, featuring four days of parades, costume contests, expert speakers

Filmed by Bike is a film festival that features the world’s best bike movies. The packed weekend includes a bike ride, visiting filmmakers, six film showtimes, dozens of films, afterparties and much more.

Burning Cat is a tabletop carnival of oversized games, comics and two-story tall cat monsters. It’s game night distilled into a weekend of creative amusements and hairy fireballs. Brought to you by the creators of Burning Kittens and The Oatmeal.

The Mt. Tabor Art Walk is a Portland tradition. This juried show and sale is a great opportunity to see quality visual art and meet artists in their studios and homes. Diverse media are represented including photography, painting, ceramics, sculpture, prints, metal arts, photography, glass, jewelry, book arts and mosaics.

At Portland’s annual Red Dress Party, all attendees are required to wear a red dress or pre-approved attire. Tickets to the event include entrance to the party, entertainment and dancing, as well as food and drinks all evening. All proceeds from this year’s Red Dress party will benefit Planned Parenthood and Q Center. Red Dress…

For more than a decade, the Kenton neighborhood has hosted a lively street fair with multiple live music stages, 80+ vendors, food vendors and plenty of great businesses on the block.

Considered the “hub” of the annual Portland Rose Festival, CityFair fills Waterfront Park with carnival rides, concerts, food and fireworks for multiple weekends during the festival.

Join one of the region’s longest-running events where more than 150 wineries and tasting rooms will host special events, capping off the state-wide celebration of Oregon Wine Month. Taste new wines from your favorite labels, sample from the barrel with winemakers or savor specialty food pairings and live music. Enjoy a winery tour or vineyard…

Portland Rose Festival features multiple parades, waterfront carnival rides, concerts, dragon boat races, fireworks and plenty of roses.

Since 2008, McMenamins Edgefield, a bucolic venue located 15 miles east of Portland in Troutdale, has welcomed musical acts to its Concerts on the Lawn series, which is a local rite of summer.

Join Portland’s roller derby team, The Rose City Rollers, for their annual Hometown Throwdown, featuring two double-headers every day. Hometown Throwdown Games in 2020: Friday, May 29:7pm Axles of Annihilation (PDX) vs. The Wall Street Traitors (NYC);9:00pm Wheels of Justice (PDX) vs. Mile High Club (DEN)Saturday, May 30: 7pm Bruising Altitude (DEN) vs. The Wall…

For more than 40 years, Portland’s Starlight Parade has offered funky, eclectic fun for everyone. From traditional marching bands and flood-lit floats, to glow-in-the-dark umbrellas and unique hand-built entries, you’ll see the best of Portland’s diverse community groups (and surrounding Northwest region) together in one whimsical pageant.

Join us in celebrating Portland’s favorite meal at the 3rd annual Portland Brunch Festival, benefiting The Jerome Kersey Foundation. This year’s festival will include local restaurants, cafes, popups, food trucks, local artists and designers. Enjoy multiple bars, a photo booth, live music, and games. Bars will be serving your favorite brunch cocktails and entertainment will…