The Sherman Theater, located at 524 Main Street in Stroudsburg, shows no signs of slowing down in its 95th year.

The Monroe County entertainment space, which opened on Jan. 7, 1929, held the gaming event Sherman-Con 2024 this past weekend. Jam band Pigeons Playing Ping Pong will perform Friday, with rock bands Static-X and Sevendust set to play the theater on Feb. 12.

Other February events include Winter Jam - featuring live music, plus art and craft vendors - and a Valentine’s cabaret and burlesque show. March highlights include comedian Drew Lynch and country singer-songwriter Brandy Clark with Hayes Carll.

Through May, the theater has shows slated for the Sherman Stage at The Renegade Winery, also located on Main Street. In recent times, the Sherman has also partnered with the Pocono Mountains Carnival Grounds in Mount Pocono and Blue Ridge Flea Market in Saylorsburg.

Later this year, “we will be a key part of bringing new, exciting events to Monroe County with our Camp Punksylvania coming to the West End Fairgrounds,” said Richard W. Berkowitz, Sherman Theater president and CEO.

The fourth punk-rock festival, set for July 5-7 in Gilbert, will feature a dozen-plus acts, including California band Diesel Boy, hitting the East Coast for the first time in 20 years.

The origins

The Sherman, which also has hosted events such as dance showcases, theatrical productions, and mixed-martial-arts and wrestling matches, initially opened as a vaudeville house. Comedy team Stan Laurel and Oliver Hardy performed on opening night.

“I imagine numerous traveling performers showed up here, along with movies,” Berkowitz said. “It was said that Roy Rogers and trigger were here, as well.”

While a 1940s-era fire damaged the theater, the Sherman - featured in Roy E. Pipher’s 2010 book “A History of the Movie Theatres in Monroe County, PA” - was not down for long.

“It was rebuilt fairly quickly, as the damage was limited to the main theater roof,” Berkowitz said. “The sprinklers in the fly tower never even went off. I replaced them when we rebuilt in 2005 and they were still stamped 1928.”

The theater, Berkowitz said, “was in operation continuously. In the 1980s, the group that owned it, the Grand in East Stroudsburg and the drive-in sold each off and the previous owner then started up with movies and special events.”

In the 1970s, “the theater was twinned so it had two sides,” Berkowitz added. “In the ’90s, they used one side for movies and concerts, and one side held a church service. It continued to operate spottily through the ’90s into the 2000s. We took it over in 2005.”

Community theater, Berkowitz said, “has always been a big part of my life,” spurring his interest in revitalizing the Sherman. Berkowitz reached out to various organizations, “but no one wanted to invest what was necessary to make it happen.

“My wife and I, along with our two small children,” he continued, “poured our heart and souls into rebuilding the theater and getting it back on its feet.”

Facing challenges head-on

Community groups using the space could not keep the theater running, thus “we merged our nonprofit with the Fine Arts Discovery series in 2008 and in 2012,” Berkowitz said. “The nonprofit took over the ownership. Somehow I stayed on.”

Berkowitz believes “we have met and exceeded our goals” for the Sherman, though success has not come easy. “I could write a book” on the challenges, he said, though “we have adapted and overcome many a time to keep the doors open and the organization growing.”

Funding, Berkowitz said, remains a challenge for the theater, as does “the chase for the entertainment dollar, casinos, big national promoters and well-healed developers.”

Despite the odds, the Sherman - with standing and seated capacities of 1,800 and 1,250, respectively - has flourished. Pollstar, a concert-industry trade publication, has ranked the Sherman among the world’s top club-sized venues on numerous occasions.

Expanding

Aside from its main venue, the theater also has the Sherman Showcase next door at 522 Main Street. The outlet, which opened as The Living Room in 2013, gives smaller acts a chance to hone their chops before playing on the theater’s big stage, Berkowitz said.

The Showcase, which had become more of an art gallery/exhibit space prior to its 2016 rebranding, focuses on music, comedy and special events.

In terms of recent additions, the Sherman opened an Arts Annex at 530 Main Street in 2023. The building houses Pocono Arts Council offices, an art gallery and expanded offices for Sherman Theater staff. The annex also secures parking for touring acts’ buses and trucks.

Though the Sherman has enjoyed many highlights - such as outdoor Labor Day weekend staple Stroudfest- Berkowitz cited one key event at the main venue: a 2010 show by Furthur. The latter band featured former Grateful Dead members Bob Weir and Phil Lesh.

Looking ahead, “the goal is to maintain a top-notch facility that serves as an economic driver to support businesses and residents of the county,” Berkowitz said. “I hope we continue to find ways to overcome obstacles so the next generation can enjoy the benefits.”