May in Portland brings back the Portland Farmers Market, Crafty Wonderland (a celebration of the city’s makers), and one of the biggest citywide events, the Portland Rose Festival. Read on for our top picks of things to do and see in May in Portland, or search our full events calendar for everything on offer.
Portland Farmers Market
Most of the area’s farmers’ markets open in May. Among the items featured are fresh produce, flowers, seafood, bread, and berries. The flagship Farmers Market is at Portland State University, but the organization operates more throughout the city. In addition to shopping, the markets can feature chef demonstrations, spontaneous music performances, fresh flowers, coffee, food carts, and more. Enjoy strolling through the market, then spend an afternoon exploring Downtown Portland.
Oregon Wine Month
Oregon is well known for its delicious wines, and the month of May celebrates that with Oregon Wine Month. Throughout the month, wineries, vineyards and tasting rooms open their doors to celebrate the return of spring and kick off the first chapter in the story of the next vintage. The wide variety of events includes new wine releases, live music and even garden tours.
Cinco de Mayo Fiesta
The largest multicultural festival in Oregon, Portland’s annual Cinco de Mayo Fiesta held at Tom McCall Waterfront Park features a wide breadth of live music, dancers from sister city Guadalajara, rides, amateur boxing and an artisan village.
Mt. Tabor Art Walk
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, glass, jewelry, book arts and mosaics.
Experience the Northwest’s biggest Lego convention. Bricks Cascade is the annual celebration of the art of Lego and the creations that are made. The convention is family-friendly, with thousands of amazing and artistic creations on display. There are also various spaces for attendees to build something as well as specialty vendors with custom-made items, mini-figures, and even vintage Lego sets.
TEDx stands for Technology, Entertainment and Design. Enjoy a day full of inspirational speakers, incredible performances and a pop-up marketplace featuring local businesses and vendors. Held at the Theater of the Clouds in the Moda Center, TEDxPortland is the largest indoor TEDx event in the world.
More than 70 years ago, the tiny town of McMinnville was struck with UFO fever when a local family spotted a flying disc from their farm, making national news. Fifty years later, in 1999, the fever descended again with the very first UFO Festival. Today you can celebrate all things extraterrestrial with other enthusiasts during days full of parades, costume contests, expert speakers and family fun.
Find yourself the perfect made-in-Portland souvenir at the city’s biggest arts and crafts market, Crafty Wonderland. This twice-yearly market draws hundreds of vendors and tens of thousands of visitors to the Oregon Convention Center in Northeast Portland. Crafty Wonderland offers accessible booth fees so that emerging artists are equally represented. Many of the makers who got their start in the market have grown into full-time businesses.
Portland Rose Festival
For more than a century, Portland, the City of Roses, has thrown itself a massive party in the form of the Portland Rose Festival. Declared the city’s official festival in 2010, the celebration includes more than 60 events, starting in late May and ending in mid-June. With the festival comes parades, carnival rides, art shows, dragon boat races, fun runs and more.
Uncover Portland’s dark side on this spine-tingling walking pub tour. In the early 1900s, unsuspecting sailors were often ruthlessly abducted and whisked away through the notorious Shanghai Tunnels. Tour guides will tell you how notorious criminals kidnapped thousands of people and why their ghosts still haunt Portland today. This is Portland’s longest-running ghost tour with…
Year-round on Saturdays, the Hollywood Farmers Markets hosts 50+ vendors, bringing you the best of the region’s agricultural bounty. In addition to amazingly fresh, local food, you’ll find live music, children’s activities, and fun events throughout the season. April through September, every Saturday 8 AM to 1 PM,October and November, every Saturday 9 AM to…
Roll out with your friends and loved ones to the monthly Gay Skate Session, held the 1st and 3rd Monday night of the month. Everyone is welcome at this all-ages event at this all-ages event. Admission tickets allow the Oaks Park Roller Rink access for the selected Gay Skate Session date/time. Includes standard skate rental.
Maximize your beach time while at the Oregon Coast Oregon’s coastline is graced with unforgettable vistas: dramatic cliffs, offshore rocks and sea lions, wide sandy beaches, majestic capes, historic lighthouses, enchanted forests and lovely small beach towns which artists and artisans make their home. Locations we may visit include: Cannon Beach, Haystack Rock, Short Sand…
Famine threatens Rome and hunger fuels the tensions between the country’s elite and the deprived masses. As civil unrest stirs political upheaval, the war hero Coriolanus is driven to defend and destroy his own country. Shakespeare’s rare and unique tragedy will be fueled by a dynamic female and non-binary ensemble and a muscular, movement-focused staging….
From Iranian playwright Nassim Soleimanpour (creator of the Off-Broadway smash hit White Rabbit, Red Rabbit) comes an audacious new theatrical experiment. Each night, a new, unrehearsed local performer joins the playwright on stage while the script waits, unseen, in a sealed box… Touchingly autobiographical yet powerfully universal, NASSIM is a striking theatrical demonstration of how…
Borderline is set in the cotton fields of Socorro, Texas, where four Latino teens threatened by a mysterious creature must rely on each other to escape the desert alive. It will take made-up myths, stories of the past, and a rendition of La Llorona to defeat the very real monster stalking children in the borderlands….
A fabulously fun award-winning musical based on the adored movie, Legally Blonde The Musical follows the transformation of Elle Woods as she tackles stereotypes and scandal in pursuit of her dreams. Action-packed and exploding with memorable songs and dynamic dances – this musical is so much fun it should be illegal. Elle Woods appears to…
Portland comics Bjorn RG and Eliza Butler host this weekly show at Neighbors Taproom with curated lineups of local and nationally touring comedians. 21+
Experience the eccentricity of Portland, Oregon and visit one of its quirkiest neighborhoods on this walking pub tour. This tour is a must-do for anyone who wants to immerse themselves in the fascinating history of the city, including stories of UFO sightings, Bigfoot sightings, exploding whales, wacky bike rides, strange locals, hijackings, hipsters, artists, and…
Chat to Steve Mason about his fifth solo album – the stirring and stunning Brothers & Sisters— and all musical touchpoints crop up. From Wu-Tang Clan and LTJ Bukem to Adam and The Ants and Public Image Limited by way of Mahalia Jackson and The Cramps, Mason not only knows his musical onions but remains…
Hosted by Nicole Onoscopi, the colorful, kooky, and highly caffeinated queen of Oregon. She and her most fantastic guest queens fill the room with laughs and great times every show. The glamour, the performances, the HAIR. Drag artistry has become globally popular with fans of all ages. Therefore, the show is rated PG-13. CELEBRATE YOUR…
Comedy Open Mic for every skill level. Beginners are welcome. Weekly mic every Monday night with 8:30 p.m. sign-ups. Hosted by Sam Bass and Milo Loza. The Cheerful Tortoise is an iconic Portland bar that has been around for more than 60 years and provides a cheerful environment for everyone to enjoy.
Celebrated photographer Elle Hygge offers professional portraits and headshots that celebrate diversity. LGBTQIA2S+ friendly and support animals welcome. This is an event sponsored by the gallery and the urban art hike to encourage everyone to come to the gallery and take pictures with art. pay the gallery @GalleryGoGoGo (3 gos) Venmo
One hundred years after he died in 1924, we celebrate a one-night-only concert featuring Giacomo Puccini’s enduring compositions. Experience the drama and passion of these cultural touchstones, brought to life by an exciting ensemble of featured guest artists. Treat yourself, get fancy with friends, and enjoy a brilliant night out. We’ll cherish the iconic music…
Talk of the Town – improvised comedy inspired by Portland’s movers and shakers. Looking for cool things to do around Portland? Curious Comedy has your back. Every third weekend of the month at 7:30 in the Annex Theatre, Talk of the Town invites special guests to tell everyone about the amazing things they are up…
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