WOODSTOCK — Comedians and filmmakers Collen Doyle and Matt Vita have always had big ambitions for the Woolen Mill Comedy Club, the stand-up venue they run on the second floor of the historic Bridgewater Mill. Despite the rural setting, the collaborators have managed to draw talent from stand-up hotbeds such as New York and Boston for their weekly showcases.
Their ambition extends to the Vermont Film Festival, a multi-day affair the pair cooked up in 2023 with the goal of exposing the state’s filmmakers to the broader entertainment industry and vice versa. With more than 40 films on the schedule, this year’s festival, which kicks off Thursday at Woodstock’s Town Hall Theatre, features the most “star-studded lineup” yet, Doyle said in a recent interview.
The crown jewel in that glittery roster is “Holy Cash,” a mobster comedy about two con artists who run into trouble when they draw the attention of the Mafia while producing a sleazy Christian show to bring in cash. The film was written and directed by comedian Paul Rodriguez, who stars alongside Emilio Rivera, Art Bonilla and part-time Vermont resident Luis Guzman, who plays God.

Rodriguez, who co-owns Laugh Factory, the famed Los Angeles comedy club, will perform stand-up at Artistree’s Grange Theatre in Pomfret on Friday night as part of the festival.
“Paul usually performs in 5- or 10,000 seat theaters, so it’s very unique to be able to see him in a small, intimate venue,” Doyle said.
Stand-up is a running theme in this year’s programming. Comic Joe List’s 2024 documentary “Tom Dustin: Portrait of a Comedian” about the Florida club owner’s career and trials with depression will screen on Friday night. List, who’s appeared on “Conan” and “The Late Show with David Letterman,” headlined the inaugural Vermont Comedy Festival, which Doyle and Vita host annually in December, back in 2022.
Meanwhile, on Saturday night, comic Noel Leon will screen her film “A Comedy of Errors,” a semi-autobiographical tale about a stand-up comedian struggling with substance abuse who relapses after her partner breaks up with her and she’s evicted from her apartment.
Leon will perform a set at the festival’s Sunday night wrap party at the Killington cocktail bar Still on the Mountain.

Interspersing comedy throughout the festival acts as a counterbalance to the more serious projects, such as “Displaced,” a short film based on writer and star Tiffany Hodges’ experience volunteering with New Sanctuary Coalition, an organization that supports immigrants at risk of detention and deportation, in New York City.
The complexities of the immigration process are a focus this year, Doyle said. Alongside “Displaced,” “Un Día Normal,” a short film about a young mother faced with deportation, will screen on Sunday afternoon.
Of the half dozen or so projects in the festival that were filmed in Vermont, one of note is “Error 404: Books Not Found,” a short documentary exploring the campus-wide backlash to the Vermont State University administration’s attempt to digitize the school’s library. The news made national headlines in 2023, and students in the university’s documentary filmmaking class got to work on the film the day after the plan was announced, with the finished project premiering on campus about a year and a half later.
Montpelier filmmaker Chad Ervin’s documentary “Gone Guys” looks at another pressing topic in the United States: the brewing mental health crisis among boys and men. Filmed in towns across the state, including Bradford, Vt., the documentary looks at the biggest challenges afflicting men and boys, from the classroom to the workplace, and what Vermont communities are doing to help.
Ervin’s short documentary “Connected: Vermont’s Grassroots Effort for Rural Broadband,” about a statewide push to bring high-speed internet to remote communities, screened at last year’s festival.
As much as the festival is an opportunity for audiences to experience a wide swath of new films, it’s also a chance for filmmakers to connect with each other.
“When you look at the great film festivals around the country, they’re great festivals because they’re great networking opportunities,” Doyle said.
With that in mind, a number of mixers are peppered throughout the festival, including an “LA style” block party, complete with margaritas and food trucks, before Rodriguez’s set in Pomfret, Doyle said.
Another mixer is scheduled for 12 p.m. to 3 p.m. on Saturday at Mountain Meadows Lodge in Killington, while Aperol spritzes and other summer refreshments will be served at 3:30 p.m. outside Woodstock Town Hall.
This year, the festival is also partnering with Ben & Jerry’s, which will be serving free ice cream during the four days of programming. Doyle noted that the brand is “very much committed right now to racial justice.” It’s also “probably the most recognizable Vermont brand in the world, so we’re really excited to be working them,” he said.
Other collaborations with Vermont companies this year include the skincare brand Ursa Major and Whisper Hill, a soap and bath products business based out of Hartford.
“I think part of the evolution of (the festival) is becoming more branded with Vermont brands and continuing to showcase great Vermont business products…,” Doyle said.
Those partnerships help give the festival the “Hollywood flair” the collaborators hope will draw more filmmakers from the wider industry, Doyle said.
“We’re still committed to indie film, (but) it’s kind of cool to start kind of breaking into more blockbuster films,” he said.
The Vermont Film Festival is slated for Thursday, July 31 through Sunday, Aug. 3. For more information and to purchase passes ($45 for a day pass; $99 for unlimited access) visit vermontfilmfestival.com. For tickets to Paul Rodriguez’s stand-up performance at the Grange Theatre on Friday, Aug. 1 ($50), visit artistreevt.org or call 802-536-1709.
Rummaging in the museum
This Saturday, Upper Valley-based art punk band, Rummager, will perform at Main Street Museum in White River Junction. Inspired by ‘90s alternative rock and experimental jazz, the five-piece band, which includes a cellist and a violist, came together last fall.
Norwich-based composer and violist Mac Waters will open for Rummager at 8 p.m. Tickets to the show are $10. For more information, visit mainstreetmuseum.org.
Percussive panhandlers
In Pomfret, Panhandlers, a 10-12 piece steel pan drum band, will perform at 6:30 p.m. next Wednesday as part of Artistree’s free Music on the Hill Summer Concert Series. The weekly program runs through Sept. 24. For more information, visit artistreevt.org.
Classical concerts
The 32nd Central Vermont Chamber Music Festival begins next Monday with concerts scheduled through Aug. 16 at Upper Valley venues including Chandler Center for the Arts in Randolph and Woodstock’s Town Hall Theatre. For more information, visit cvcmf.org.
