Improv comedy mines Cold Spring’s past
It’s one thing to get a laugh at a party, but imagine if the host announced that within a few minutes you’d spin it into a witty performance.
That was the challenge for The Town Criers, an improv group that performed at the Chapel Restoration in Cold Spring on March 15, using odd moments of local history as prompts.
The concept is the brainchild of Beacon resident Joanna Castle Miller, who runs Wait Don’t Leave Productions. Lisa Pertoso, a former Beacon resident who lives in Manhattan, co-produced the show and performed. The pair have written for Comedy Central, The Onion, Funny or Die and McSweeney’s. Four veteran comedians — TJ Del Reno, Anne Hogan, Aaron Kheifets and Valerie Lynn Brett — rounded out the cast.

The Town Criers emerged from an idea Castle Miller and Pertoso had to base improv on letters to the editor of small-town newspapers. They tested the concept at the Beacon Bonfire Festival in 2023 when Castle Miller read letters aloud and Pertoso and her compatriots improvised scenes. Castle Miller said an audience favorite tackled the “old Beacon versus new Beacon” debate.
Because Castle Miller likes projects about historical memory, she wanted to expand the idea to include old news stories. In a 2024 performance at the Chapel Restoration, The Town Criers focused on West Point Foundry history, which proved to be a hit.
Before a full house on March 15, the format expanded to include three sources: Castle Miller interviewed Philipstown native Nat Prentice, asking him about local life in his teenage years; she read 19th-century news clips; and the audience shared examples of quirky incidents.
The improvisers heard the material for the first time along with the audience.
Photos by Ross Corsair
“We want to give people a different window into how interesting and deeply human our history can be,” Castle Miller said, adding that “a little absurdity” in historical events helps create entertaining skits.
Prentice talked about the 1960s, including his memories of Palen’s Drug Store and sneaking an underaged beer at McConville’s (now Doug’s Pretty Good Pub). He shared less-pleasant accounts of his Little League team in Garrison losing virtually every game to the Cold Spring Yankees.
He said teenage boys got their haircuts at Sam Sunday’s Barber Shop while the barbers smoked foul-smelling cigars. The boys’ mothers would not let them go near Gus’ Barber Shop because it had adult magazines.
Castle Miller provided historical tidbits from Looking Back columns in The Highlands Current and the newspaper archives at fultonhistory.com. One story from around 1900 described how a resident swindled out of $10 decided not to prosecute but was quoted saying he “hoped to get even.”
She was especially taken by Irving P. McCoy, who made news as a boy by falling through the river ice near the Pacific Hotel (now the Hudson House). At least one other boy also fell in before friends formed a human chain to rescue them.
McCoy, quoted as yelling, “I want to be dry!” grew up to become editor of The Cold Spring Recorder. He claimed his office cat wrote letters for him.
When McCoy angered local Democrats by publishing a letter from Republican Gov. Teddy Roosevelt, McCoy formed his own political party. When no one else attended its first meeting, he appointed himself president and his cat as secretary.
The audience contributed oddities including unsolved mysteries, such as how B Street got its name, the theft of a disco ball from the bandstand and someone who found a stranger in their car after a pizza date. They also mentioned a desperate shopper who urinated in an antique shop vase and ceramic bells that conjured up elves, fairies and spirits in the Nelsonville Woods.

Asked which scenes went especially well, Pertoso said, “Our shows go by so fast, it’s hard to remember,” although she did single out the barbershop girly mags. “One of my favorite things about improv is when we subvert expectations,” she said. “The implication was that there were adult magazines there, but we flipped it around to be feminist literature, like Gloria Steinem.”
“They turned it into, ‘Your mom doesn’t want you to see feminist literature, it might radicalize you!’” Castle Miller said.
With only a few chairs as props, the cast relied on pantomime and quick wit to create scenes from Garrison-Cold Spring baseball games, visits to Palen’s and witches in the Nelsonville Woods. There was also young Irving McCoy stuck in the frigid Hudson and a scene starring his literate cat. The troupe even pinned the theft of the disco ball on a B Street resident.
Pertoso said one principle of improv is that there are no mistakes. “As long as we support our fellow players, it can’t go wrong,” she said. “We go in with zero expectations — the beauty of this art form is that shows are once-in-a-lifetime.”
Castle Miller noted the importance of research. “The better you know the town you’re performing in, the more audience reaction you’ll get,” she said.
Will The Town Criers return? “Absolutely!” Castle Miller said.