A Moving Picture Show: Boondocks Film Society’s Traveling Community
With food, drinks, music, and celeb sightings, Boondocks has become a monthly must.
The Boondocks Film Society, a roving pop-up cinema and event series, has been bringing the four counties of the RI region together for films, food, music, and spectacle more or less monthly since 2017. From curated menus and live performances to surprise celebrity appearances, their happenings transform nostalgic art-house film screenings into full-bodied cultural gatherings that draw loyal crowds across Connecticut, the Berkshires, and the Hudson Valley.
The first time Boondocks Film Society founders Cindy Heslin and Jeff Palfini rented North Canaan’s Colonial Theater, they weren’t plotting a business plan so much as chasing a feeling. They had driven past the dormant marquee for years before finally stepping inside the beautiful old theater. “We just rented it, and it was pretty cheap,” Heslin recalls. “We wanted to show a movie that we love, and try to get some friends and family out.”
Cindy Heslin and Jeff Palfini. Photo courtesy of Boondocks Film Society.
Their debut pick, Emir Kusturica’s Arizona Dream, set the tone for what Boondocks would become: parties celebrating movies that carry nostalgia, strangeness, and, above all, the joy of watching a film with an audience. For Boondocks, the place, the music, the food, the feeling, and the people are as essential as the film itself.
“Creating a pop-up series rather than having a home creates challenges,” says Palfini. “But it’s great to get to build a special event for new people, with different businesses. They don’t have to come to us. It’s fun that we’re in their backyard.”
A packed house...er, park for August's screening of ‘Amelie.’ Photo courtesy of Boondocks Film Society.
A Boondocks night begins with a happy hour before the film, full of thematic play. The menu of food and cocktails is curated to match the screening, and local musicians riff on the film’s soundtrack.
Early in its existence Boondocks screened Hayao Miyazaki’s Porco Rosso in an airplane hanger with poke bowls and sesame noodles from Shiro, aviation cocktails mixed with Berkshire Mountain Distillers gin, and Big Elm “Fatboy” IPA—an aeronautical menu for the pilot-pig fable. In Amenia, they partnered with the Four Brothers Drive-In for large-scale events such as Close Encounters of the Third Kind. More recently, they showed MacGruber with the film’s director, Jorma Taccone on hand for a pre-show talk. Fireworks ended the over-the-top extravaganza that featured video messages from the film’s stars and a surprise cameo from Lin-Manuel Miranda in the audience.
MacGruber director Jorma Taccone and Lin-Manuel Miranda at the Four Brothers Drive-in in Amenia. Photo courtesy of Boondocks Film Society.
Another evening at South Farms in Morris, Connecticut, featured a screening of You Can Count on Me, complete with an on-stage Q&A with actress Laura Linney, live music by Billy Keane, a menu by Chef Carl Ciarcia, and themed cocktails.
While summer outdoor events can feel expansive and even raucous, the winter circuit leans more intimate and eclectic. At The Moviehouse in Millerton, Tangerine was paired with a pre-film DJ set by Ethical Drift. In Hudson, a spooky-season screening of The Lost Boys at Story Screen included a performance by a band calling itself the Bloodsucking Brady Bunch.
After every show, guests leave with a bespoke movie poster designed by a local artist—often Heslin herself. The tradition, inspired by the founders’ fondness for the Fillmore Theater in San Francisco, is a key component of the Boondocks experience. “It makes it real,” says Palfini.
The first of many posters designed by Cindy Heslin. Photo courtesy of Boondocks Film Society.
Film choices, they emphasize, come from the instincts of their small organizing team, which also includes local cinephiles David Ruchman, Alix Diaconis, and Rufus de Rham. “We try to choose just favorites. Ones that we really love and that we want to see with an audience,” Heslin explains. “I love to hear people laughing and talking afterward.”
Coming out of the pandemic, Palfini says it felt essential to offer “a communal film experience again.”
With their monthly success, some might expect Boondocks to settle into a permanent theater of their own. They even once passed on the chance to buy the Colonial. But Palfini reflects, “we’re happier in a place where there aren’t as many financial pressures. In this format we can play around and not have to worry about what’s going to sell tickets.”
Local musician Eleanor Friedberger performs before a recent screening. Photo by Alix Diaconis.
Over the past eight years, the model has proven remarkably elastic—filling drive-ins, barns, ski lodges, hangars, and historic theaters—without losing its through-line. At its core, Boondocks remains modest and portable: a good print in an interesting space, a reason to arrive early, and a memento to take home.
As Heslin puts it, “It’s really about community.”
The next Boondocks event in September is still to-be-determined (keep watch on their social media pages for eminent details) but with Halloween around the corner Palfini did announce that they will be putting on Donnie Darko at Story Screen in Hudson in late October.
