Indie Out: Boondocks Film Society Produces Cool Movie Events

When Cindy Heslin and Jeff Palfini first met at a film festival in 2010, they knew they shared a passion for indie releases. It wasn't until Heslin overheard Palfini make an obscure reference to an offbeat 90s comedy at a pizza joint weeks later that she knew they were kindred spirits. Their story could have ended there: Two flim buffs fall for one another over pizza and beers. Instead, after their lives took a few twists and turns, the two launched Boondocks Film Society last year, producing monthly film events throughout the Berkshires, Litchfield County, and the Hudson Valley.

A Boondocks event isn't your typical movie night out. The films are screened in funky venues--an airport hangar, a ski lodge, a shuttered theater, to name a few. Themed cocktails, food, art and music all play a role in transforming what is usually a private experience (you and your bucket of popcorn and jumbo soda) into a social one (you gleefully clinking your glass, filled with glow-in-the-dark ice cubes, with the stranger seated next to you).

The concept percolated for a few years before it took off. Shortly after they met, Heslin decided to take a four-month, cross-country trip in her van--a solo "walkabout," she says. She wound up in San Francisco, and Palfini, who had lived there previously, joined her. While they were in San Francisco, they immersed themselves in the area's robust film scene. One of their favorite haunts was the city's Castro Theatre, a historical movie palace that hosts repertory movies, film festivals, and special events. In San Francisco, Palfini also helped to produce a film event in a decommissioned U.S Mint building.

But in 2016, the two decided it was time to take a break from city living and move closer to their families on the East Coast. So, they decamped to sleep Cornwall, Connecticut and often trucked to theaters as far away as Brooklyn to find movies that were unconventional. "We were starving for the arthouse programming we had in San Francisco, but there's not a lot of unique places in the area that show cult, classic or foreign films," says Palfini, 44, a freelance copywriter.

Then, last spring, they learned they could rent the defunct Colonial Theater, a monumentally ornate Colonial Revival building in North Canaan, Connecticut. "We both love vintage single-screen theaters," says Heslin, 33, who works as an artist's assistant. The Colonial, with its plush red-cushion seats and retro styling, proved the right fit for their first screening, Arizona Dream, a 1993 cult classic starring Johnny Depp, Lili Taylor, Faye Dunaway, and Jerry Lewis.

"It's a Serbian Film that didn't get a lot of attention in the United States, but it has a lot of known actors, so that was enough to get people interested in coming out to see it," she says. Since then, the couple has held nine other film events, including Porco Rosso in a hangar at the Walter J. Koladza Airport in Great Barrington, where they served aviator cocktails; and Better Off Dead in a lodge at Catamount Ski Resort, featuring food plated on recycled cardboard "TV dinner" trays, arguably tastier fare than the frozen variety featured in the cult ski film. On April 20, Miller's Crossing was planned at Berkshire Mountain Distilleries in Sheffield, and on May 25, they will be at Four Brothers Drive-In in neighboring Amenia, New York, for a Tim Burton double feature: Pee Wee's Big Adventure and Mars Attacks.

With more people watching films at home and online, Boondocks needs to give them a reason to get off their couches. They put a lot of thought into each screening to make it feel like a special, one-off experience, partnering with local restaurants, breweries, and distilleries to create themed menus. The film posters are designed by local artists; some movies feature live music by local bands.

Even though the screenings attract between 80 and 150 people, depending on location, the cost to stage each event can run between $1,200 and $2,300. The couple is working on becoming a 501(c)3 nonprofit, which will allow them to apply for grants and enlist volunteers. They are also trying to draw a younger audience--judging from the abundance of man buns and combat boots in the crowd at any given event, they're succeeding. One reason is that tickets are only $12 when purchased ahead through their website and $14 at the door. Dinner is usually $12.

Youth doesn't really define the Boondocks audience, though. Eclectic, maybe. And a Boondocks event feels more like a club, where you're likely to run into a lot of the same people and meet new ones, which appeals to Amillie Coster, 34, of Lenox. "The event format and cool venues bring out dozens of people, some who you might know, some new people who may become great friends," she says.

Film screenings are posted online in advance, but the menu and drinks are usually kept under wraps until movie night. Says Palfini: "We want to keep people guessing."