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SEE: First Thursday in the Pearl District
Even though it’s been happening literally every first Thursday of the month since 1986… We’re here to remind you that this Thursday is, in fact, First Thursday in the Pearl District. Each month, the pop-up street gallery—featuring a showcase of original, handmade artwork by local Portland artists, and the thousands of patrons who show up to peruse—completely takes over a few blocks in Northwest Portland. May’s featured artist is Mary Garcia (@marythewilder on IG), whose vibrant, oft-mushroom-inspired art is the perfect ode to spring in the Rose City. As the night goes on, First Thursday becomes kind of an unofficial “going out” destination for Portland’s 20-somethings, so choose your perusal time wisely—depending on whether you wanna beat that crowd, or join ‘em. Various locations in the Pearl District, urbanartnetwork.org, 5–9 pm Thursday, May 2. Free.
GO: The Language of Sneaker Design at Tomorrow Theater
As part of the Portland Art Museum’s First Free Thursdays, “Design Language of Sneakers” offers a deep conversational dive into the creative processes of prominent sneaker designers. The event, which also celebrates PAM’s Future Now: Virtual Sneakers to Cutting-Edge Kicks exhibition, gives attendees a window into the fusion of art, culture and technology that goes into designing sneakers that serve as artistic canvases for millions. A panel discussion—featuring Ty DeHaven (HILOS) and Laurance Bass (Pensole Lewis College of Design), and moderated by Sneaker Week PDX co-founder Herbert Beauclere—centers on the shoe’s impact on fashion and functionality, serving as the crossroads of design and innovation that make sneakers a cultural staple. Tomorrow Theater, 3530 SE Division St., 503-221-1156, tomorrowtheater.org. 7–9 pm Thursday, May 2. Free.
LAUGH: Rip City Comedy Festival
The Rip City Comedy Festival debuted last year in Portland’s walkable Southeast District with a packed weekend of headliner comics from across the country and throughout the Pacific Northwest. The festival returns this year with a lineup of popular local favorites and out-of-towners, with themed shows, feature showcases, and free panels of industry-leading professionals. Festivalgoers have the option of a three-day wristband or finding individual shows to their liking throughout this event, seeing the state of Portland comedy today. Multiple locations, ripcitycomedyfest.com. Various times on Thursday–Saturday, May 2–4. Prices vary. 21+.
HEAR: Sounds of Brazil PDX
The roots of jazz in Brazil include the sounds of Choro, an instrumental genre that more than a century ago birthed Brazil’s first “urban pop” music. Sounds of Brazil PDX, an upcoming concert at Portland State University, offers a journey through a tapestry of Brazilian music, showcasing the works of 20th century composers Pixinguinha and Jacob do Bandolim, along with many more. Audiences will experience the complex melodies and rhythms of classic and modern Choro, as well as the beats of Samba, brought to life across three distinct acts, with special guests Alexandra Santos (vocals) and Anderson Reis (percussion). Lincoln Recital Hall, Room 75, 1620 SW Park Ave., 503-725-3305, bit.ly/3w6ywlk. 8–10 pm Friday, May 3. $15–$20.
ATTEND: Crafty Wonderland
Portland’s biannual art and craft fair, Crafty Wonderland, serves as a showcase of creativity and local talent. Inspired to create an indoor marketplace for our unpredictable Portland rainy days, co-founders Torie Nguyen and Cathy Zwicker have seen the event blossom into one of Portland’s biggest arts and crafts markets, featuring over 225 local vendors offering one-of-a-kind handmade wares. The Friday night pre-show party will start things with a limited-ticket event, giving attendees first pick of exquisite items, along with a complimentary drink to sip as they browse. All weekend, attendees will be on the alert to win one of the fair’s goodie bags handed out randomly throughout the day filled with locally made swag. Oregon Convention Center, 777 NE Martin Luther King, Jr. Blvd., 503-224-9097,craftywonderland.com. 5–9 pm May 3, 11 am–5 pm May 4. $4–$25
GO: Lil’ America Cinco de Mayo Fiesta
What’s better than celebrating Cinco de Mayo? Beginning the festivities a day early. On Saturday, May 4, Lil’ America—Portland’s BIPOC and queer-focused food cart pod—hosts its second annual Cinco de Mayo Fiesta and, trust us, you don’t want to miss it. There will be a live DJ (@kidflowerz on IG), dance lessons, a whole lotta food specials at the carts (the street tacos from Los Plebes are fire) and, perhaps most crucially, a Don Julio 1942 tequila tap cocktail takeover at Fracture Brewing. Viva la tequila! 1015 SE Stark St, lilamericapdx.com, Noon-6 pm Saturday, May 4. Free.
ENJOY: Portland Cinco de Mayo Fiesta
Portland’s Cinco de Mayo Fiesta celebration features an array of traditional foods, music, crafts, and more. Included will be the sounds of internationally acclaimed Mariachi Ciudad de Guadalajara, direct from the city of Guadalajara, and Oregon’s Ballet Folklórico México en La Piel, a group that uses Mexican folkloric dance as a way to remember the traditions of their ancestors. Other highlights include a Family Fun Carnival, Rip City Boxing, the Cuervo Premier Tequila Tasting Experience, and a lotería/bingo game booth with prizes. Tom McCall Waterfront Park, 98 SW Naito Parkway, cincodemayoportland.com. 11 am–11 pm Friday–Sunday, May 3–5. $10–$25.
WATCH: Portland Derby
Hold your horses, the 17th Portland Derby is back for another year of fierce competition between the ponies and the fashion-forward. Dig out the flamboyant hats, matching outfits, and dapper suits for the most thunderous two minutes. The annual “Run for the Rose City” is the social event of the spring to see and be seen at, so let the best hat win. The Redd on Salmon Street, 831 SE Salmon St., portlandderby.com. 11 am–6 pm Saturday, May 4. $25–$35.
GO: Indigenous Culture Day
Indigenous Culture Day honors the traditions and knowledge of Indigenous Peoples while allowing communities to engage with cultural heritage. Hands-on activities like cordage making and basketry, coupled with the immersive experiences of storytelling and learning about first foods provide a cultural experience for the community. Participants will take a short forest walk from the Tryon Creek Nature Center and surrounding trails to witness the traditional lifeways of the Northwest and celebrate the reclamation of traditional lands for Indigenous Peoples. Tryon Creek State Natural Area, Southwest Terwilliger Boulevard, tryonfriends.org/calendar/culture-day-2024. 9 am–3 pm Saturday, May 4. Free.
DRINK: PDX Urban Wine Experience
The PDX Urban Winery Association celebrates Oregon Wine Month with its 10th annual PDX Urban Wine Experience. This event features 18 local Portland winemakers with an array of 34 wines from 25 different varieties. Attendees can sample these selections along with a delightful charcuterie cone from Charcuterie Me. If you’re looking to snag a few different bottles of wine, there will be discounts on purchases of six and 12 bottles, allowing a mix of favorites from various wineries. A portion of proceeds from every ticket and bottle of wine sold will support Street Roots, dedicated to social justice and providing income opportunities for people experiencing homelessness. Easton Broad, 237 NE Broadway, pdxurbanwine.com/pdx-urban-wine-experience/pdx-urban-wine-experience-2024. 2–5 pm Sunday, May 5. $45.