Tim Meadows Credit: Courtesy

Actor and comedian Tim Meadows, who headlines this year’s Vermont Comedy Festival at the Woodstock Town Hall Theatre, jokes that white people frequently mistake him for fellow actor Don Cheadle. It happens so often that Meadows’ FAQ page includes only one question: “Is Tim Meadows Don Cheadle?”

The Detroit native, known for his 10 seasons on NBC’s “Saturday Night Live” and such movies as Mean Girls, Wayne’s World 2 and Dream Scenario, also enjoys riffing on his beleaguered hometown. As he told a crowd recently at New York City’s Gotham Comedy Club, “If you ever get out of New York and go to Detroit for a visit and find yourself in a nice area, I got news for you: You’re in Chicago.”

Meadows is one of about 60 standup comedians who will take the stage this week at the third annual Vermont Comedy Festival, the state’s largest gathering of standup comedians. From Thursday through Sunday, December 5 to 8, comics from across the U.S. and Canada will perform at five Upper Valley venues. Many of the shows are free, including those at Still on the Mountain in Killington, Long Trail Brewing in Bridgewater Corners and the Ottauquechee Yacht Club in Woodstock.

Nadia Quinn Credit: Courtesy of Eleonora Briscoe

The lineup features Nadia Quinn, a New York City stage and screen actor, singer, and standup comic who appeared in Steven Spielberg’s 2021 West Side Story, the HBO series “Succession” and the ABC sitcom “Black-ish.” On Sunday at the Woolen Mill Comedy Club in Bridgewater, she’ll do a holiday version of the show she performed at the Edinburgh Festival Fringe show in August, which was critically acclaimed and covered in the New York Times. The show, which she performs with her husband, Aaron Quinn, highlights the couple’s many musical talents in songs such as the risqué “Everyone’s a Little Bisexual.”

Also on the bill is Nikki MacCallum, another New York City comic whose solo off-Broadway musical comedy show, Adulting for Idiots, won Best Musical at the 2023 United Solo festival.

Max Higgins Credit: File: Luke Awtry

Among a few local faves on the festival program is Max Higgins. The bespectacled comic, formerly of Burlington, got his start in comedy while attending the University of Vermont and won the 2023 Seven Daysie for best standup comic in Vermont. Though he recently moved to Brooklyn, he’ll be back for midnight shows on Friday and Saturday at the Woolen Mill Comedy Club.

“I was never much of a girl,” Higgins joked about coming out as trans at a show earlier this year at Burlington’s Vermont Comedy Club. “I was about as much a girl as three children stacked in a trench coat are an adult.”

The Vermont Comedy Festival is the brainchild of Collen Doyle and Matt Vita, thirtysomething actors and comedians who’ve run the Woolen Mill Comedy Club in Bridgewater for the past 10 years. The festival, which draws more than 1,000 attendees annually, is considered the unofficial start of Wassail Weekend, a 40-year winter tradition of food, music and holiday revelry in Woodstock.

Following a kickoff party at Ramunto’s Brick & Brew Pizza in Bridgewater, the festival will begin with the head-to-head 1 Minute Stand Up Battle at the Woolen Mill Comedy Club on Thursday. Fifty comedians each perform a one-minute standup act, and the audience decides which of them move on through four rounds. The winner is invited to headline a show at the Woolen Mill at a later date. Last year’s winner was Dennis Rooney, a staple of Long Island’s comedy scene.

“It’s a super high-energy show,” Vita said. “A lot of people say it’s one of their favorite shows of the festival each year.”

Vermont Comedy Festival, Thursday to Sunday, December 5 to 8, various locations. Free-$45.

The original print version of this article was headlined “Fest to Kill | Vermont Comedy Festival returns with its largest lineup of regional and national standup acts”

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Staff Writer Ken Picard is a senior staff writer at Seven Days. A Long Island, N.Y., native who moved to Vermont from Missoula, Mont., he was hired in 2002 as Seven Days’ first staff writer, to help create a news department. Ken has since won numerous...