Tired of "fun is back" messaging? Too bad! It is! While Portland skies stubbornly cling to the final bits of spring, Portland's social calendar is gearing up for the most liberated summer of the 2020s so far. We're talking music festivals, arctic Chekhov, runway shows, and (a lot) more. Keep scrolling for our cream-of-the-crop picks, and check back throughout the season as the list grows.

Opacity of Performance

Portland choreographer Takahiro Yamamoto brings a live dance installation to PAM’s gallery of European art. Curtains will section off individual performances, toying with perspective and visibility to make audiences do what audiences love: consider the potentially violent effects of their gaze. June 16–26, Portland Art Museum

Pat Regan

The New York–based comedian, Hacks writer, and podcast cohost is, put simply, one of the funniest people currently alive. His ultra-reflexive, deceptively thoughtful lexicon infects the brains of all who encounter it, and his mid-June Mississippi Studios date is not to be missed. June 19, Mississippi Studios

Pickathon

After a two-year pause, the eco-friendly Happy Valley music fest returns. For four days at Pendarvis Farm, catch a (pretty thrilling, if we do say so ourselves) mishmash of locals and national names: Hurray for the Riff Raff, Valerie June, L’Rain, Faye Webster, and Armand Hammer among them. Aug 4–7, Pendarvis Farm 

The Cherry Orchard

The Portland Experimental Theatre Ensemble’s long-delayed production will take Chekhov’s tale of aristocratic unease to the tundra. Drawing on elements of the Russian master’s unfinished final play, plus contemporary climate anxieties, the always-reliable company will “step out from the shadow” of past Cherry Orchards to “make something of [their] own,” per director Alice Reagan. June 24–July 9, Reed College Performing Arts Building

Risk/Reward Festival

Let us take a moment to celebrate the real win of this new, liberated phase of the pandemic: the return of weird-ass performance festivals. Risk/Reward is always a trip, and for its fourteenth year, it will present five new works from seven artists at Portland Center Stage’s downstairs studio. June 24–26, Ellyn Bye Studio at Portland Center Stage 

Chamber Music Northwest Summer Festival

Under the theme “Inspirations and Influences,” Chamber Music NW presents a sprawling monthlong ode to the ways composers shape and impact one another. With in-person and virutal concerts, galas, late-night musical mixers, and more, prepare to immerse yourself in classical compositions from across the globe. June 25–July 31, citywide

Waterfront Blues Festival

Dads, rejoice: for its 35th anniversary, the Blues Fest is returning to its rightful home. After one year off and another at Zidell Yards, the festival’s 2022 iteration will light up good ol’ Tom McCall once again for the first weekend in July. (Non-dads should be excited about this as well.) The stacked lineup includes Grace Potter, Lady A, 20 Feet from Stardom star Judith Hill, and dozens more. July 1–4, Gov. Tom McCall Waterfront Park

Portland Fashion Week

Sustainability is the name of the game at this 21-year-old bonanza: it’s a plastic-free zone where experts and amateurs alike gather to gawk at gorgeous gowns. This year’s theme is “Keep Portland Pretty,” with 8 p.m. shows nightly in a variety of categories at downtown’s new(ish) Moxy Hotel. Aug 16–21, Moxy Hotel