Sterling Opera House, Derby: Connecticut's Haunted Theater With a Jail Below

The Sterling Opera House faces the Derby Green from Elizabeth Street, a tall Italianate Victorian building with rows of arched windows. Upstairs is a horseshoe-shaped auditorium with a sweeping balcony. Downstairs, until 1965, were Derby’s city hall, its police station and its jail cells.

It closed more than 60 years ago and has hardly been opened since, and in the dark it acquired a ghost reputation to match its looks: a little boy whose ball rolls across the balcony, a man in a brown suit, a woman in white, children’s voices. Syfy’s Ghost Hunters investigated in 2011. Here is the building’s history, the stories, and what is planned for it.

History of the Sterling Opera House

Derby in the 1880s was a busy mill town at the meeting of the Housatonic and Naugatuck rivers, and it wanted a public building to match. The answer combined civic offices and entertainment. The opera house was named for Charles A. Sterling, founder of the Derby-based Sterling Piano Company, and designed in the Italianate Victorian style by New York architect H. Edwards Ficken. Boxes on either side of the stage were built to show off Sterling pianos.

It opened on April 2, 1889, with James A. Herne’s play Drifting Apart, which lost money. The theater did better after that, and for more than half a century it brought national acts to the Naugatuck Valley. Harry Houdini performed here, and so did Red Skelton, Lionel Barrymore and the boxer John L. Sullivan. Amelia Earhart spoke here on March 16, 1936, and D.W. Griffith’s The Birth of a Nation was shown on its screen. Bob Hope and Bing Crosby are said to have played it too.

The lower two floors and the basement housed Derby’s city hall and police station, with jail cells beneath the stage, so prisoners and performers worked under the same roof. The last show, a minstrel production put on by a local club in late 1945 for soldiers coming home from the war, ended the opera house’s life as a theater. City hall stayed until 1965, when it moved out and the building was closed. A few rusted cells and artifacts remain in the basement.

On November 8, 1968, the Sterling became the first building in Connecticut listed on the National Register of Historic Places. It has been closed ever since. The exterior has been kept up, but the interior is peeling and damaged, and bringing it up to code would cost millions. Restoration plans in 2011 put the cost at $3 to $4 million and won a $150,000 federal grant for cleanup. In 2023 the state budget set aside $100,000 to study repairs, and in November 2024 Derby’s Board of Aldermen voted unanimously to seek firms to document the building and plan its restoration to how it looked in 1889.

The ghosts of the Sterling Opera House

The boy with the ball

The best-known story is of a little boy in the balcony. Rich DiCarlo, then Derby’s cultural commissioner and head of the Valley Arts Council, described seeing a boy’s figure and a ball moving there. Paranormal investigators have said a playground ball rolled across the theater for no reason, and some versions name the boy Andy. Derby’s Mayor Anthony Staffieri told the New Haven Independent in 2011 that “the weirdest things happen to me there,” citing cold breezes and flashlight batteries that died without warning.

The man in the brown suit

A gentleman in a brown suit has been reported in the building, and storytellers say he is Charles Sterling, who is said to have died before the opera house was finished. Nobody is recorded as having died in the building itself.

The woman in white and the dressing rooms

DiCarlo also described a full-figure woman in a teal dress in a dressing room. Others report a woman in white, shadows in the balcony and children’s voices throughout the building. In the sub-basement, by the old cells, visitors have said they were touched, and that they heard a child’s voice say “Help me.”

Ghost Hunters

The Atlantic Paranormal Society investigated for Syfy’s Ghost Hunters in the winter of 2011, in an episode that premiered on April 20, 2011, partly in hope of attracting an investor. The team reported high EMF readings in a building with no power, whispers in the balcony and a childlike voice, but the ball they left on the second floor did not move, and they said a crackling in the sub-basement could be vermin or settling debris. Their verdict was that something might be going on and that it deserved a return visit after renovation.

Where to look

• The balcony: where the boy and his ball are reported, and where Ghost Hunters heard whispers.
• The dressing rooms: where the woman in the teal dress was seen.
• The sub-basement and jail cells: below the old police station, where visitors report being touched.
• The Derby Green: the only place you can stand today: the building’s best face is the Elizabeth Street front.

Visiting the Sterling Opera House

The opera house is closed to the public and has been sealed for years. You can see it from Elizabeth Street and the Derby Green, and it looks its best at dusk. Locals recall occasional open days in the past, such as a short theater tour on Derby Day in 2011, so watch for city announcements as restoration work moves forward.

Derby has embraced its ghostly side in other ways: the state tourism office lists a paranormal dinner and tour in Derby on its 2026 haunted map. For a full night investigating a haunted building, Haunted Rooms runs overnight ghost hunts at Captain Grant’s, 1754 in Preston, and Union Cemetery in Easton, home of the White Lady, is about 25 minutes away by daylight.

• Visiting Closed and sealed; see it from Elizabeth Street and the Derby Green
• Ghost hunting No public investigations; the building is closed pending restoration

Tips for your visit

• See it from the Derby Green at dusk.
• Do not try to enter: the building is sealed and unsafe inside.
• Watch for city announcements of open days as restoration moves forward.
• Pair it with a daylight visit to Union Cemetery in Easton.
• For an after-dark investigation, book a Haunted Rooms ghost hunt.

More haunted places nearby

• Union Cemetery, Easton: home of the White Lady, about 25 minutes west
• Gunntown Cemetery, Naugatuck: a colonial cemetery with ghost stories, about 20 minutes north
• Remington Arms, Bridgeport: the haunted munitions works, now demolished
• The 1754 House, Woodbury: a haunted colonial inn you can stay in
• Haunted places in Connecticut

Sources

Facts on this page are checked against the official website, historic records and news coverage. Ghost stories are reported as staff, visitors and investigators tell them, and we say where records contradict a story.

• Wikipedia: Sterling Opera House
• NBC Connecticut: Phantoms in the opera house (2011)
• NBC Connecticut: Hidden in plain sight, inside Derby's Sterling Opera House (2019)
• Damned Connecticut: Ghost Hunters at the Sterling Opera House
• CT House Democrats: Restoration plans in motion at historic opera house (Nov 2024)
• Connecticut Office of Tourism: Haunted Connecticut map (2026)