Pedalpalooza is a monthlong party on wheels.

Pedalpalooza

Thru June 30 
There is perhaps no better time to ride a bike in Portland than June. Among the reasons why: Pedalpalooza, a monthlong velostravaganza featuring hundreds of rambles for riders of all propensities, from family-friendly jaunts to the flesh frenzy that is the World Naked Bike Ride (June 29). Whether you’re looking to get wild or wonky, click here for five best bets. 

Chef in the Market 

Thru Oct 12, PSU Farmers Market 
Cooking for you each Saturday morning at the Portland State University Farmer’s Market: culinary masters like Leena Ezekiel of Thali Supper Club, Eric Joppie of Olympia Provisions, and Cathy Whims of Nostrana. The pièce de resistance? After each class, a free tasting! The Lents International Farmers Market will also host demos this summer; dates TBD. 

Portland Pride Festival 

June 15–16 
The annual LGBTQ+ Waterfront fest, which dates back to the mid-’70s, is basically a weekend-long, fiercely inclusive street party, crowned by one of the city’s largest (and most fabulously rambunctious) parades. 

Original Practice Shakespeare Festival 

June 21–Aug 25 
OPS claims to produce Shakespeare the way it was done in the Bard’s day: with minimal rehearsal, an onstage prompter, and plentiful audience interaction (choose your seat accordingly). The company has 19 (!) plays in its repertoire this summer, with showings scheduled at parks across the city. 

Concerts in the Park 

June 21–Sept 1 
Pick any evening this summer; there’s likely to be a free concert at a park near you—thanks to this major volunteer-led effort spearheaded by Portland Parks & Recreation along with the Portland Parks Foundation. Here are just a handful of this summer’s free park concerts: 

  • July 6: Georgina Band, Floyd Light Park 
  • July 10: Mel Brown B-3 Organ Group, Dawson Park 
  • July 27: Turquoise Pride, Cully Park 
  • Aug 6: Farnell Newton & The Othership Connection, McCoy Park 
  • Aug 8: Chervona, Wellington Park 
  • Aug 10: Portland Festival Symphony, Laurelhurst Park 
  • Aug 31: Sakumuna, Overlook Park 

Movies in the Park 

June 21–Sept 1 
For some, free park concerts are just pre-gaming for the main event: outdoor movies screened at sundown, all summer long. Here are just a few: 

  • June 21: Black Panther, King School Park 
  • July 25: Incredibles 2, McCoy Park 
  • July 26: Spider-Man: Into the Spider-Verse, Unthank Park 
  • July 28: E.T., Wellington Park 
  • Aug 8: Coco, Woodlawn Park 
  • Aug 15: Slumdog Millionaire, Laurelhurst Park 
  • Aug 23: Mary Poppins ReturnsLuuwit View Park 

Prince Sing-Along 

7 p.m. Sat, June 22, Pioneer Courthouse Square 
The Low Bar Chorale (previously the OK Chorale) is a no-skills-required, drop-in adult choir that meets bimonthly at Revolution Hall to sing an ever-changing lineup of hits. Now, the group hosts its first official all-ages event: a free Prince sing-along at Pioneer Courthouse Square to mark the 35th anniversary of Purple Rain, with the masses led song by China Forbes (of Pink Martini), Edna Vazquez, and others. Expect that album nearly in its entirety (“Darling Nikki,” for obvious reasons, will be skipped), plus other Prince hits. 

Sunday Parkways

11 a.m.–4 p.m. occasional Sundays thru Sept 23 
On select Sundays throughout the summer, the city creates car-free zones for folks to safely run, bike, roll, and stroll. A mega-family-friendly way to explore your own neighborhood, or a new one. 

  • June 30: North Portland 
  • July 21: Outer Northeast Portland 
  • Aug 25: Green Loop (Downtown/Central Eastside) 
  • Sept 22: Northeast Portland 

Portland Street Fairs 

Various dates and locations 
Practically every week this summer, a Portland thoroughfare will close to traffic in favor of foot traffic, food, free entertainment, and fun. Here are some highlights: 

Ten Tiny Dances 

10 a.m.–1 p.m. Sat, July 13, downtown Beaverton 
Constraints are said to be good for creativity, a maxim embraced by this beloved performance series since 2002. As the name suggests, expect 10 different dance pieces popping up on five four-by-four-foot stages across downtown Beaverton. You’ve got three hours to catch them all. 

Cathedral Park Jazz Festival

July 19–21, Cathedral Park
For three days every July, just below the St. Johns Bridge, you’ll find the longest-running jazz and blues festival west of the Mississippi. The fest, now in its 39th year, invites audiences to spread their picnic blankets and enjoy tunes from 15 bands, many of them local.

Portland Zine Symposium 

July 20–21, Pacific Northwest College of Art 
Now in its 19th year, this free celebration of indie publishing returns with a weekend of panels, tabling, and skill-share workshops. 

PDX Pop Now

July 20–21
The long-running, all-ages, always-free fest is one of Portland’s absolute best. Details for this year's fest are scant, but stay tuned.

Flicks on the Bricks

Fridays, July 26–Aug 23, Pioneer Courthouse Square
Portland’s living room gets extra cozy every summer, with classic and family-friendly flicks played on a gargantuan inflatable screen. Bring a pillow and snacks for maximum fun. 

Portlandia Mermaid Parade

Noon Sat, July 27, Japanese American Historical Plaza
The incomparable Una the Mermaid hosts the fourth annual installment of this annual parade, a gender-fluid, family-friendly, body-positive gathering of merpeople of all stripes.

Galaxy Dance Festival

Aug 1–4, Director Park
Free dance classes and performances at Director Park, with opportunities to see (and learn) ballet, hip-hop, belly dance, modern, and more. 

Washington Park Summer Festival

6 p.m. Thu–Sun, Aug 1–4, International Rose Test Garden Amphitheater 
This free four-night fest, organized by Portland Parks & Rec, showcases an eclectic array of art, music, and performance, including jazz, Native American dance, Italian opera and Portland Cello Project performing Radiohead, Coltrane, and Bach.

Lents Chicken Beauty Contest 

11 a.m.–4 p.m. Sun, Aug 11, 9330 SE Harold St 
Mirror, mirror, on the wall, who’s the most beautiful clucker of them all? That’s up to visitors to the Lents Street Fair, which holds its fifth annual poultry pageant this month. Past years have featured a broad array of fowl, from dramatically crested Polish chickens to glam silkies to Naked Necks (which cofounder Jonah Willbach says rarely come close to winning). 

Portland Adult Soapbox Derby

10 a.m.–4 p.m. Sat, Aug 17, Mount Tabor
Every year, the laws of gravity, aerodynamics, and creative whackery warp as homemade conveyances hurtle down the twisty slopes of Mount Tabor in an expletive-filled race to the bottom. High-velocity hijinks guaranteed.

Jade International Night Market 

5–10 p.m. Saturdays, Aug 24 & 31, PCC SE Campus 
The annual event in Southeast Portland’s Jade District seeks to educate people about issues affecting the neighborhood, celebrate the diversity of its communities, and support small local businesses. Expect multicultural foods, shops, and performances. 

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