What to Do in Portland (Aug. 30-Sept. 5, 2023)

GO: Vacancy Side Street Block Party

Don’t miss the chance to be a part of Vacancy PDX’s first-ever ticketed block party (atop a freshly paved lot) featuring an inspired blend of fashion, music and art. A vendor village will take over a segment of Northeast 22nd Avenue right next to the multipurpose artist collective space, where you can shop for clothing, jewelry and crafts; skateboard through the pop-up park; or take aim at the Liquid Death Dunk Tank. The side street is minor-friendly until 7 pm—that’s when the event’s three bars open for business and a lineup of musical acts take the main stage, including Bobby Raps and Sean Anonymous. Vacancy PDX, 2137 E Burnside St., Unit C, vacancypdx.com. 3-11 pm Thursday, Aug. 31. $15-$50.

WATCH: Black Friday

Described as a “celebration of Black creativity and innovation,” Black Friday is a new event that spotlights entrepreneurs of color in the Portland community through film and conversation. You can expect to see two shorts that tell the stories of Paul Knauls, the unofficial mayor of Northeast Portland and former co-owner of the heralded Geneva’s Shear Perfection beauty salon and barbershop; Portland Trail Blazers DJ O.G. One; and downtown BIPOC enterprise hub Creative Homies. In addition to the screening, Micro Enterprise Services of Oregon executive director Cobi Lewis will lead a panel discussion featuring business leaders like Stephen Green, the founder of Pitch Black PDX, which hosts a series of events that support Black business owners; Paige Hendrix Buckner, CEO of All Raise, a nonprofit that empowers women and nonbinary individuals in the tech sector; and Marquita Jaramillo, the principal of the Black Founders Matter Fund, which is used to invest in Black-led companies that are in the early stages of development. Hollywood Theatre, 4122 NE Sandy Blvd., 503-493-1128, hollywoodtheatre.org. 6:30 pm Friday, Sept. 1. $20 general admission; $15 seniors, students and children.

WATCH: The First Annual Most Pageant: Main Event!

The ultimate queer extravaganza awaits at the Most Pageant, where one of seven fabulous finalists will be crowned The Most! Yes, all of the categories you’d expect to see at a Miss U.S.A. competition will be there, including talent, interview and eveningwear, but this contest takes its inspiration from the raucous tradition of drag queen pageants and underground balls, promising an experience that’s much more entertaining than spending hours watching women from each state parade around in gowns and talk about world peace. This event proudly has no boundaries, and when anything goes everything glows! Clinton Street Theater, 2522 SE Clinton St., 971-808-3331, cstpdx.com. 8 pm Friday, Sept. 1. $15. 21+.

WATCH: BitNile.com Grand Prix of Portland

Some people like to use Labor Day weekend to find quiet solitude in nature. Others prefer to spend the unofficial end of summer listening to the roar of turbocharged motors making laps around Portland International Raceway. This IndyCar Series race returns for its 29th year—this time with a slightly creepy blended-reality e-commerce company as the title sponsor—with 10 races from five different series, including NASCAR’s minor league circuit, the Automobile Racing Club of America’s stock car program and a youth division. The event everyone is there to see, of course, is Sunday’s IndyCar run, which could be the decisive factor in the championship chase. During the past four Portland Grands Prix, the driver who came away with the most points ended up claiming the Astor Cup. Portland International Raceway, 1940 N Victory Blvd., raceportland.com. Gates open 8:30 am Friday-Saturday and 9:30 am Sunday, Sept. 1-3. $25-$165.

GO: The Mid-Autumn Moonlight Market

Most Oregonians want to pump the brakes on summer rather than coast into the chilly rains of fall, however, this event isn’t ushering in the season of Pumpkin Spice Lattes (however, those did drop on an alarmingly early date—Aug. 24). The Mid-Autumn Festival is a cherished holiday in China that honors the Harvest Moon, the full moon closest to the autumn equinox. The Lan Su Chinese Garden has its own version of that celebration, which will kick off with a free lion dance at the entry plaza. Beyond that, visitors can listen to music played on a yangqin (a Chinese dulcimer), watch calligraphy demonstrations, and meet the revered Moon Rabbit (which in this case is played by animals from the nonprofit Rabbit Advocates). There will also be illuminated lion dances in the garden every single evening of the festival. Lan Su Chinese Garden, 239 NW Everett St., 503-224-8455, lansugarden.org. 2-9 pm Friday-Sunday, Sept. 1-3. $10-$25.

LISTEN: 10th Annual Montavilla Jazz Festival

If you love jazz, you won’t want to miss this sprawling festival that showcases original compositions by some of our city’s best performers. Concerts take place at multiple venues across the city, so be sure to check the schedule ahead of time in order to catch your favorite artists. The festival culminates with a special performance by internationally acclaimed drummer Alan Jones playing alongside Grammy Award winners Tivon Pennicott and Kevin Hays. Friday: Mt. Tabor Park Caldera Amphitheater, Southeast 60th Avenue and Salmon Street. Saturday and Sunday: Alberta Rose Theatre, 3000 NE Alberta St.; Portland Metro Arts, 9003 SE Stark St. Friday-Sunday: The 1905, 830 N Shaver St.; Vino Veritas Wine Bar and Bottle Shop, 7835 SE Stark St.; montavillajazz.org. Various times Sept. 1-3. Prices vary.

GO: Art in the Pearl Fine Arts & Crafts Festival

If we must bid farewell to summer, might as well do it as vibrantly as possible. For the 27th year, Art in the Pearl will take over the North Park Blocks this Labor Day weekend. And it just might take you all three days to wander through the labyrinth of booths and displays—more than 100 artists are expected to participate. Bonus: The festival is free to attend. North Park Blocks, 235 NW Park Ave., 503-512-9071, artinthepearl.com. 10 am-6 pm Saturday-Sunday, 10 am-4 pm Monday, Sept. 2-4. Free.

WATCH: Tina – The Tina Turner Musical

In the mood for a musical that will leave you feeling empowered, inspired and energized? Look no further than Tina – The Tina Turner Musical, which is making its local premiere. Broadway in Portland’s second show in the 2023-24 season tells the story of one of the most iconic and influential musical artists of our time. Turner overcame adversity to become the Queen of Rock ‘n’ Roll, selling more than 200 million records and winning 12 Grammys during her career. Consider this series of performances (which are already selling quickly) a fitting tribute to the late artist, who died earlier this year at the age of 83. Keller Auditorium, 222 SW Clay St., 503-417-0573, portland.broadway.com. 7:30 pm Tuesday-Friday, 2 and 7:30 pm Saturday, 1 and 6:30 pm Sunday, Sept. 5-10. $30-$144.75.