Search May Events
Embrace spring with events celebrating local food, crafts and Latinx culture.
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.
Bricks Cascade
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.
TEDxPortland
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.
UFO Festival
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.
Crafty Wonderland
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.
More May Events 2024
Check out our picks for top things to do in May in Portland.
Hollywood Farmers Market
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…
Kaliente Drag Brunch
Kharisma brings the heat with Kaliente, the newest Drag Brunch at your Stag PDX. Start your month with a bit of spice every 1st Sunday, with a show that has that extra kick that only Kharisma and her special guest performers can bring. Enjoy all-you-can-eat brunch options served from the buffet with mimosas available -…
Gay Skate
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.
UFO Festival
Every May, thousands of visitors flock to the city’s famous UFO Festival, featuring four days of parades, costume contests and expert speakers.
Multnomah Falls & Gorge Waterfalls Tour
Prepare to journey back in time to the birth of the Cascade Mountain Range, where lava and pyroclastic matter oozed and flowed, creating a solid layer of basalt rock that coated Western Oregon. Fast forward to the Pleistocene Ice Age, and witness the epic Lake Missoula Flood, which carved out the majestic Columbia River Gorge,…
Portland City Tour
Get ready to explore the heart and soul of Portland with a half-day City Tour. This isn’t your average tour; you'll be takn on a journey through the city’s charming streets and reveal its laid-back atmosphere. Brace yourself for an amazing tour of Portland’s must-see spots like the International Rose Garden (seasonally), the World Forestry…
Full Day Columbia River Gorge Tour
Jump into a day-long adventure and discover what makes the Columbia River Gorge National Scenic Area a true gem. Be awed by the majesty of the USA's second tallest waterfall, witness the incredible salmon journey at the Bonneville Dam Complex, catch some windsurfing thrills in the windsurfing capital of the USA, and explore the official…
Mt. Hood Loop Tour including Multnomah Falls
Buckle up for an epic journey as you are whisked away from Portland to the spellbinding Mt. Hood. With passionate and well-informed guides leading the way, you’ll have plenty of chances to snap up some breathtaking shots of the majestic landscape and soak up the mesmerizing history of this iconic mountain. Enjoy a full day…
Multnomah Falls & Gorge Waterfalls & Wine Tasting Combo
Beginning in the Cascades and moving upriver through the eastern stretch of the Columbia River Gorge is the relatively young but rapidly growing wine-making region known as the Columbia River American Viticulture Area (AVA). Often referred to as “A World of Wine in 40 Miles,” the Columbia River AVA consists of a combination of climates,…
Oregon Coastal Tour
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…
Portland City Tour & Gorge Waterfalls Combo
Ready for an adventure? Join the ultimate tour of Portland and the Columbia River Gorge. You'll see the must-see sights in Portland and then be whisked away to the stunning Columbia Gorge National Scenic Area. Discover the magic of the waterfalls, soak in breathtaking views, and dive into the history of the area’s top attractions….
Private Oregon Coast Brewery Tour
Hop aboard a ride from your swanky Portland hotel and savor the stunning views of Columbia River's bustling ship traffic. The first stop? Two of Astoria's coolest breweries, where you can sip on the finest brews and grab a bite to eat. Fort George BreweryAstoria Brewing CompanyReach Break BrewingBuoy Beer CompanyRogue AlesGeek out with the…
Private Elevated Wine Tour Experience
Oregon is home to some of the most beautiful vineyards in the world, not only known for its distinctive pinot noir but many other varietals such as pinot gris, chardonnay, riesling and more. Your experience will take place in the heart of the Willamette Valley, home to renowned, award-winning wineries. Oregon's Willamette Valley has elevated…
BeerQuest Haunted Pub Tour
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…
Coriolanus
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….
Nassim
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…
Multnomah Falls, Train Ride, & Wine Tour
Get ready to be swept off your feet by your guides as they take you on a journey of a lifetime through the stunning Columbia River Gorge and the Hood River Valley. Brace yourself for a riveting tale of this breathtaking terrain and its awe-inspiring past. And just when you thought it couldn’t get any…
Oregon Wine Tasting Tour
Sip your way through Oregon’s finest wines on an extraordinary tasting tour, only a day trip away from Portland. Discover the stunning Willamette Valley, and be guided through the best wine experiences it has to offer. Soak up the breathtaking views, visit three amazing vineyards, and unveil the secrets behind the perfect Oregon Pinot Noir….
Borderline
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….
Legally Blonde The Musical
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…
Bangerz Comedy
Portland comics Bjorn RG and Eliza Butler host this weekly show at Neighbors Taproom with curated lineups of local and nationally touring comedians. 21+
Goodness the Comedy Show
Goodness is a show that brings the best stand-up comedy in Portland to the incredible Laurelhurst Club! Tickets are only $10, with even more affordable drinks! (21+)
Weird Portland Pub Tour
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…
Steve Mason
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…
Shakespeare's First Folio: 1623–2023
It’s difficult to imagine now, but when William Shakespeare died in 1616, over half of his plays had never been published. As a playwright, actor, and shareholder in his theater company, Shakespeare was, above all, a man of the stage, and there is no evidence to suggest that he sought to preserve his playwriting legacy…
Gabriel Kahane + Pekka Kuusisto: Council
After nearly a decade of musical friendship, it seems only fitting that the cult American singer-songwriter Gabriel Kahane and iconic Finnish musician Pekka Kuusisto have formalized their collaboration under the moniker Council. They present an evening of intimate and sonically varied songs and chamber music written during several writing retreats in Northern Karelia and Portland,…
New Beginnings
In the season of new beginnings, the Portland Youth Philharmonic Orchestra, Conservatory Orchestra, Wind Ensemble, and String Ensemble present a concert filled to the brim with brilliant new music by Polina Nazaykinskaya, Giancarlo Castro D’Addona, and Nancy Ives. The 2023 PYP Concerto Competition Winner, still to be announced, will perform their winning piece with the…
Drew Holcomb & The Neighbors
Drew Holcomb has always charged listeners’ hearts and minds while inspiring them to find joy and community in their 15 years of nonstop touring. And never more so than on his latest album, Dragons. His most collaborative record to date features artists and songwriters, including Lori McKenna, Natalie Hemby, Sean McConnell, The Lone Bellow, and…
Cheerful Tortoise Comedy Open Mic
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.
Michelle Wolf
Wolf has quickly become one of the most influential voices in the comedy landscape, with the Village Voice calling her “the voice comedy needs right now” and The Daily Beast declaring, “Michelle Wolf is the future of stand-up comedy.” Her most recent Netflix special, MICHELLE WOLF: JOKE SHOW, received high praise and her first hour-long…
Puccini: In Concert
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…
Antonio Rey
Many flamenco aficionados consider Antonio Rey to be the heir apparent to Paco de Lucia’s throne. His career began at the age of ten. He was soon performing on international stages and winning prestigious awards for his incredible virtuosity, such as the Premio Nacional de Guitarra (also won by Paco de Lucia and Vicente Amigo),…
Talk of the Town: Improv Show
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…
Drag Brunch at The Pharmacy
Join hostess Devlin Lynn Phoenixx and her cast of talented queens for a Sunday brunch experience you won’t soon forget. Your ticket includes admission to the show, your meal, AND your first mimosa. Vegetarian, vegan, and gluten-free options are available. So grab your friends and get down to The Pharmacy for a spectacularly fun time.
Cadenza Series: Spring Concert
The Portland Youth Conservatory Orchestra, Wind Ensemble, and Percussion Ensemble invite you to their Spring Concert. PYP Conductor Giancarlo Castro D’Addona leads the Portland Youth Wind Ensemble, Lawrence Johnson conducts the Portland Youth Conservatory Orchestra, and Gordon Rencher coaches the Portland Youth Percussion Ensemble.
Fatai
Come and see Fatai and her stupidly-vibing band for an evening of phenomenal music. Featuring songs from her new EP and her infamously flipped covers, this tour will be one not to miss.
A Century of Unforgettable Music
PYP concludes its centennial season with a performance of Franz Schubert’s Unfinished Symphony – the first piece ever performed by this orchestra, formerly known as the Portland Junior Symphony. Don’t miss your last chance to be thrilled by Season 100’s Portland Youth Philharmonic on the Arlene Schnitzer Concert Hall stage. PYP welcomes special guests to…
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