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.
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.
Oregon Wine Month
You can celebrate Willamette Valley wine all year round, but especially during Oregon Wine Month, when the entire state joins in commemoration of the beloved industry for the month of May, offering special activities and promotions for the enjoyment of Oregon wine. There are all kinds of specials going on in honor of Oregon Wine Month. Find…
Wooden Shoe Tulip Festival
Colorful fields reminiscent of Holland burst with acres of tulips in full bloom at the Wooden Shoe Tulip Festival in Woodburn.
First Thursday in the Pearl District
Starting in 1986, First Thursday in the Pearl is a district-wide celebration on the first Thursday of each month. Originally a gathering of art collectors and dealers, the celebration has grown to a monthly event of over ten thousand people, including art enthusiasts, wine aficionados, and scenesters looking to see and be seen. Art galleries in…
Karaoke From Hell
The Northwest's original live karaoke band, Karaoke From Hell, has been rocking Portland for over 25 years and counting. The catalog boasts nearly 700 songs for you to sing, covering every genre from show tunes to skate punk. Catch it every Monday at Dante's and every Thursday at The Spare Room.
Crafty Wonderland Spring Art + Craft Market
Meet the makers. Over 250 artists will be selling their goods at the Crafty Wonderland Spring Art + Craft Market. Crafty Wonderland is excited to be back in person for the Spring Art + Craft Market Pre-Show Ticketed Shopping Event on Friday General Admission – Timed Entry Tickets on Saturday
Haunted Shanghai Tunnel Tour
Old Town Pizza & Brewing is built directly above Portland's infamous Shanghai tunnels. The same tunnels that were used to house kidnapped sailors during the early 1900s. Book a tour and explore the rich history of Portland, and the legacy of Old Town.
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…
Portland Saturday Market
Open every Saturday from March–December, Portland Saturday Market is the largest arts-and-crafts fair in the U.S.
Portland Thorns FC
Watch the Thorns play at Providence Park. Established in 2012, the team began to play in 2013 and placed third in its inaugural season and, in the playoffs, won the first NWSL championship. The club won the NWSL Shield in 2016 and a second NWSL Championship in 2017. 2020, they won the Community Shield with the best…
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.
St. Johns Bizarre and Parade
The St. Johns Bizarre is a uniquely crafted celebration that kicks off Portland's summer street fair season. Held annually on the second Saturday in May, the Bizarre brings music, crafts, and food to the crowds who traditionally attended the St. Johns Parade. After the parade, a portion of the business district in St. Johns is…
Mother's Day Cruise
Sweep mom off her feet this Mother’s Day with a special brunch cruise. The whole family will enjoy a two-hour cruise on the Willamette River, a delicious Northwest brunch buffet, mimosas or sparkling cider, live piano music and beautiful river views. Make memories that Mom will treasure forever.
Portland Timbers
Head to Providence Park to watch the Portland Timbers take on their rivals. Cheer with the Timbers' Army at Providence Park and become part of a Portland tradition.
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.
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, photography, glass, jewelry, book arts and mosaics. The Mt. Tabor Art Walk…
Rockwood Market Hall Music Series
Each month, on a late Sunday afternoon, the Rockwood Market Hall hosts a local artist to perform for community members who enjoy their food while listening to live music in a relaxed, laid-back atmosphere. With various cuisine options, the Rockwood Market Hall is a great place to enjoy dinner with family and friends. See you…
West End Wednesdays
West End Wednesday exists to ignite new energy and define a common vision for downtown SW Portland. Building relationships with neighbors and business partners is not just organizing a once-a-month event… it is actively creating, together, a neighborhood everyone can love to live, work and play in. West End Wednesdays is the West End's signature celebration…
Portland Night Market
The Portland Night Market showcases many unique businesses that call Portland home. Blending food, culture, music, drinks and retail for an adventurous evening in the Central Eastside. Meet some of Portland's best makers and creators. With almost 200 hundred makers, the Night Market offers food carts, drinks, clothing, lifestyle goods, home goods, body care and art. The Portland…
Portland Rose Festival
Portland Rose Festival features multiple parades, waterfront carnival rides, concerts, races, fireworks and plenty of roses.
Rose Festival CityFair
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.
Portland Flea + Food
The Portland Flea + Food is a gathering place for the creators, curators and collectors held the last weekend of the month from April to October in Portland, Oregon. Every market features 80+ local artists, makers, and curators of the best vintage, handmade and locally sourced goods in town. Saturdays at Ecotrust: 721 NW 9TH AVE Sundays at Nova…
Half Day Gorge Waterfalls Tour from Portland
Species seen nowhere else in the world, dramatic basalt lava flows nearly a mile deep, and some of the world’s most beautiful waterfalls are a few of the sights that await you on this tour. Experience the grandeur of the Columbia River Gorge, one of the United States’ most photographed National Scenic Areas. We will…
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…
Throughlines: Connections in the Collection
Throughlines embraces wonder and curiosity, bringing together artworks from across the Museum’s collections to explore the range of artistic innovation. From diverse geographies, cultures, and time periods, artists have consistently created images, objects, and experiences that ask us to consider ourselves and the world from different perspectives. Visitors will encounter playful groupings that reveal how artists…
Full Day Gorge Waterfalls and Mt. Hood Tour from Portland
Follow the path of an ancient riverbed, carved by the last ice age, past the Bridge of the Gods, and explore the Windsurfing Capital of the World. In the afternoon, traverse Oregon’s fertile fruit valley on the way to the alpine top of a volcano, which boasts a title as the world’s 2nd most summited…
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…
Gorge Waterfalls and 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 combines climates, soils, elevation, and geology…
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…
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 Brewery, Astoria Brewing Company, Reach Break Brewing, Buoy Beer Company, Rogue…
Tyrannosaurs – Meet the Family
Tyrannosaurs – Meet the Family brings the latest tyrannosaur discoveries to life, overturning preconceptions about these ferocious predators. The exhibition explores the most feared and revered of all dinosaurs in new and different ways. The exhibition’s real and replica specimens are spectacular in scale and form and reveal some of the most significant discoveries…
Future Now: Virtual Sneakers to Cutting-Edge Kicks
Future Now: Virtual Sneakers to Cutting-Edge Kicks is a groundbreaking new exhibition that features nearly 60 futuristic footwear designs pushing the boundaries of what art can be. Featuring an incredible mix of fashion, design, gaming, new media, architecture, and material arts as well as sustainable and collaborative practices, the exhibition features work by designers as diverse…
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…
Oregon Jews, A to Z
The Oregon Jewish Museum and Center for Holocaust Education provides a home for a bountiful collection of archival materials and artifacts. Our collection includes thousands of photographs, documents, films, oral histories, three-dimensional objects, and artworks — the physical objects that represent the Jews of Oregon. Oregon Jews, A to Z highlights the most significant, poignant,…
The Burned Piano Project
Over several weeks in spring 2022, as lilacs bloomed in Portland, a mosque, a Black-owned restaurant and two synagogues were vandalized. Around that time, a family's home, which also was a Jewish organization's mailing address, was destroyed by arson in the middle of the night. The family will not be named for their protection. A…
Head Games Trivia
General knowledge trivia combines movie clips, sound effects, pictures and popular music to give players a one-of-a-kind two-hour experience. The pace is relaxed, so there is plenty of time to buy food and drink. Win gift cards and more. Free to play, show up early to get a spot.
Head Games Trivia Night
Live multi-media trivia every Wednesday at 6:30 p.m. Free to play. Win prizes. Teams of up to 6. Please arrive early for best seats. General knowledge trivia combines movie clips, sound effects, pictures and popular music to give players a one of a kind 2-hour experience. The pace is relaxed so there is plenty of…
Jamie Lissow
Actor and comedian Jamie Lissow is currently a regular weekly guest on the #1 rated late-night talk show, Gutfeld! on Fox. Jamie is best known for his starring role in two seasons of the Netflix Original Series “Real Rob”, alongside SNL alums Rob Schneider, Adam Sandler, Norm MacDonald and David Spade; a show Jamie co-wrote…
Drag Bingo
Get your ass to The Houston Blacklight for DRAG BINGO hosted by the one + only Peachy Springs every first Wednesday of the month. Play your favorite geriatric game-gone-glamorous with the queen of bingo for a chance to win prizes. Get there early cause they've got drink specials, and your girl’s got a following.
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 language can both divide…
Coco
Coco — the project of Maia Friedman, Oliver Hill, and Dan Molad — began as an experiment of sorts; three friends writing songs for nothing other than the ritual of doing so. “There’s a mutual admiration and trust among us,” the band shares. “It allows a ‘first thought best thought’ mentality.” Their vast and varied…
Rip City Comedy Festival
A 3-day celebration in support of the vibrant and diverse Portland comedy scene. Featuring national headliners, including Steve Agee, Natalie Palamides, AJ Wilkerson and more. Please visit the website for links to tickets, schedules, and updated performance listings.
Full Day Oregon Coast Tour from Portland
With over 300 miles (482 km) of public coastline, Oregon’s beaches are sure to amaze with their dramatic offshore rock formations and reborn beach towns. This tour will travel along one of the most picturesque driving routes in the country, U.S. HWY 101. Spend the day exploring breathtaking beaches, trekking along sandy shores, and viewing…
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…
Water Media Juried Show
The Gallery at OSA is pleased to announce the Spring Water Media Juried Show. This exhibition invites submissions in all types of water-soluble media, such as watercolor, gouache, acrylic, chalk pastel, etc. Whether your watercolors drip and flow or you dry brush acrylic paint, this is work created in water-based media. Open to any and…
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….
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