The first two years of Kickstand’s Comedy in the Park summer series were impressive, but 2023 blew them both away, with Portland Parks & Recreation staff counting approximately 4,700 people on a recent Friday in August.

That’s people-protesting-against-Donald-Trump numbers. But while anger frequently provides the motivation of our moment, Kickstand brought all those people out to make them laugh, and in doing so, to showcase and support local comedians and community. 

Now, as Portlanders gaze skyward and feel the first drops of autumn rains, the comedy nonprofit faces a moment of truth. Who will follow them indoors, into their in-flux brick and mortar clubhouse?

Since April, Kickstand has been renting and renovating a 4,750 sq foot building at the corner of Southeast Hawthorne and Southeast 10th—the former fútbol (soccer) pub Toffee Club. Working with Harka Low Carbon Architecture, the renovations will create an 80-seat mainstage theater for shows and separate rooms for development nights and classes.

“It’s going to be a place where the opener for whoever’s headlining at Helium could have their own smaller show,” Kickstand’s artistic director and founder Dylan Reiff said, proposing a hypothetical scenario. “It’s a place where local performers can grow their ideas, build out shows, and reach audiences. You know, hot date night, hang out, laugh, check out a work in progress, work out your own material, work out new ideas.”

Reiff’s mention of Helium isn’t meant as competition. Kickstand’s proposal for moving into the Hosford-Abernathy neighborhood—just two blocks from Helium and 10 blocks from Funhouse Lounge—hopes to create something the organization calls a “comedy corridor.” Based on the same location idea of fast food restaurants and gas stations clustering together to draw customers to an area, Reiff said he hopes the same approach can work here.

“The actual competition is Netflix. Streaming. Staying home is the only real competition to going out to see live arts. It’s not another comedy theater,” he said.

This isn’t Kickstand’s first attempt at creating a permanent venue. The upstart improvisers started out in 2014, in the basement of a now-closed bike shop bar called Velo Cult, where they held popular improv shows in a windowless room, for four months, until fire inspectors told them to knock off the unsafe practice. The Siren Theater took them in next, renting the troupe the second floor of their former Old Town location. By 2019, Kickstand was a nonprofit—teaching classes and bringing comedians from neighboring scenes to Portland. The vibe was “DIY club brings like-minded boundary-pushing groups to play shows and make new connections,” but it was comedy. When Kickstand decided to take over the Brody Theater they were working to preserve a place of local improv comedy history, create stability for the organization, and expand. Of course, then the pandemic happened.

“We started that renovation on March 7, 2020, and we ended it on March 11,” Reiff explained wistfully. Kickstand had been awarded a $150,000 grant by Prosper Portland to pay for those renovations, but eventually gave the entire amount back. As luck would have it, the organization has been able to secure a similar grant for the new building.

“Prosper Portland has really been just so helpful,” Reiff explained. The Prosper funds, along with grants from Travel Portland and the Portland Events & Film Office, are essentially earmarked for the current renovation—getting things ready to open the doors. None of it is part of the million dollars Kickstand hopes to raise over the next five years—to purchase its building.

“The goal for fall was to make it to fall,” Reiff said. The popularity of Comedy in the Park proved good for fundraising. “God bless Venmo for finally working with nonprofits. We knew that classes would be fine. And classes have continued to sell out.”

In a move that is extremely what Kickstand Comedy would do, the organization began teaching classes in the unrenovated space as soon as they started renting it. So although Reiff says the plan is to begin holding shows there in October, it’s hard to say how polished the place will be. Kickstand is taking over the lease for the entire lot, but local brewers Away Days have a lease for their taproom through the end of the year.

Eventually, Away Days plans to move their Portland taproom to a larger space in the Brooklyn neighborhood. And while we pressed the brewery’s co-owner Niki Diamond about a brilliant community-focused future of soccer, comedy, and Fresh-Hop English Pales, she said Away Days simply needs more room. And they want a beer garden. 

So Kickstand is still searching for someone to move into the Away Days space next year, but comedy fans might be able to grab a pint until the holidays—it’s not yet clear how it’ll work. Reiff calls the side of the building with Away Days’ taproom a “makerspace” because he’s trying to leave potential for what could go into it—it’s a small brewery now, but there’s room for other options.

The Kickstand side has a full kitchen, but his team has no interest in running it. “Our background is not food and drink, so we want to work with people who are passionate and excited. A goal would be to also cross pollinate audiences. I’m hopeful that the spaces can be a community where everyone’s cup gets filled.”

The last Comedy in the Park of the season was September 1, but Kickstand is still producing shows around town until its new space opens. kickstandcomedy.org