Kit Williamson’s Official “EastSiders” Guide To The Perfect Cross-Country Road Trip

The uproarious queer web series is back for Season 3.

In the new season of Eastsiders Cal and Thom naively attempt to fix their relationship while on a 16-state road trip from New York to L.A.

It’s one of the most logistically challenging setups you can imagine and writer-director Kit Williamson (who plays Cal) says between schedule conflicts, budget constraints, freak weather and near-impossible terrain, it was a gay miracle they completed the three-week trek.

A behind-the-scenes photo from Season 3 of Eastsiders of…yes, eating cheese in Wisconsin!

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But they did, and Season 3 is even funnier, sweeter, and messier than ever, as the gang addresses infidelity, promiscuity, substance abuse, and more. It also marks the return of Constance Wu (Fresh Off the Boat), Wilson Cruz (Star Trek: Discovery), Stephen Guarino (I’m Dying Up Here) and Drag Race star Willam Belli, as well as appearances by Tuc Watkins, Colby Keller, Traci Lords, Matthew Wilkas, Max Emerson, and Williamson’s husband, actor John Halbach.

With production in the rear-view mirror, we asked Williamson to share his tips on attempting The Great (Queer) American Road Trip.

  1. DO check the weather.

    “I’ve always wanted to go to Yellowstone, so I scripted that into the trip,” Williamson says. “Unfortunately, we got snowed out by a freak blizzard, so we only got up to the entrance of the park and didn’t get to shoot the blowjob scene at Old Faithful like I wanted.”

  2. DO practice driving a trailer before buying one.

    Season 2 ended with Cal and Thom in New York, and Williamson initially considered setting Season 3 set in the Big Apple. “But by the time we got the financing I was ready to move back to L.A. My husband and I missed it too much,” he reveals. “Then I decided that there needs to be a way to get the character back to L.A., so Cal and Thom buy a vintage trailer and go on a road trip.”

    “I wanted them to explore the uncharted waters of their 30s together,” he adds, “because the characters have been marked by an extended adolescence and immaturity. So, this is an opportunity for them grow up, come hell or high water.”

    But Williamson had never driven a trailer before. “There’s a difference between driving a trailer and driving a trailer around a mountain range in Colorado,” he shares.

  3. DONT’ hook up with drifters.


    Cal and Thom hook up with porn star Colby Keller in Season 3, but Williamson warns of getting too close to handsome drifters. “That’s sage advice dating back to Thelma and Louise, which is actually what we titled that episode. It’s a meta-commentary on knowing you shouldn’t do certain things, but doing them anyway against all advice.”

  4. DO use your journey as a social-media opportunity.

    Put 'em up! Have you checked out the new season of @eastsiderstv yet? #WhereGentlemenGo #gaylosangeles #gaywesthollywood

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    On the road Williamson and husband and co-star John Halbach started a travel blog, Where Gentleman Go, documenting their lives and travels as newlyweds. “It’s also a platform for other travelers and influencers to share their experiences.”

  5. DON’T forget to score free water from Wall Drugs.

    Carol M. Highsmith/Buyenlarge/Getty Images

    “I recommend checking out the Badlands in South Dakota. It’s a striking sight and ,on your way there, you definitely must stop by Wall Drugs. That place is an institution.”

  6. DO come up with an alias.


    The crew secured campground locations for a shoot in Idaho and all seemed well—until they told them the name of the project. “After that, the campsites bailed on us,” Williamson reveals. “We speculated it was homophobia because it’s easy to Google what EastSiders is about. So we called it Go West instead, and said it was just about two friends traveling west. Then we didn’t have any problems.”

  7. DON’T let them tell you this isn’t your country.

    “There was one scene at a gas station in Wyoming where we thought there would be an issue,” he shares, “but it turned out fine. But maybe that’s because of my cisgender, male, white-presenting privilege.”

    But Williamson says he was ready if things went south.

    “Just try to fucking hate-crime me, Wyoming—I’m a black belt in Taekwondo. It’s 2017, and I don’t care who’s president, it’s our country, too. We have a fucking right to every fucking inch of this country, and I would encourage every fucking gay couple to claim it all.”

  8. DO end your journey in Malibu.


    “There couldn’t be a better sense of relief than when we put our feet in the sand and watched the sunset,” says Williamson. “Our Herculean task was over, and we just soaked it all in.”

Season 3 of EastSiders is available on iTunes, Vimeo, Amazon Video, Google Play, and


Arthur Tam is a Hong Kong-based journalist and former editor at Time Out Hong Kong.