Worcester activist David T. Webb was convicted Monday of trespassing in a case that posed an unusual question: Could flying a drone onto property from which he had been barred amount to trespassing even if Webb himself never set foot there?
A Worcester District Court judge concluded that it could.
Judge Michael Welsh found Webb guilty following a bench trial Monday, Aug. 3, according to the Telegram & Gazette. Webb was acquitted of two additional charges of disorderly conduct and disturbing the peace.
Welsh sentenced Webb to 30 days, time served, according to the Telegram. Webb’s attorney, Samantha Beauchamp, told the newspaper that he plans to appeal the conviction.
The case stems from a Sept. 5, 2025, incident outside Worcester City Hall. Court records obtained by the Worcester Guardian show Webb was charged with the three offenses following an investigation into a drone flown over a crowd gathered at the Main Street entrance plaza.
According to a statement of facts filed in Worcester District Court, a City Hall security officer reported seeing a small drone, described as approximately four inches square, hovering between four and 15 feet above the crowd at about 11:25 a.m.
The security officer identified Webb as the person operating the drone, according to the court filing.
At the time, Webb was subject to a no-trespass order barring him from Worcester City Hall and several surrounding areas. The order, originally issued in May 2025, cited alleged harassment of city employees who reported feeling unsafe or fearful and had recently been extended for another year, through May 2027.
The police statement filed in court says the order prohibited Webb from accessing City Hall offices and adjacent areas, including the parking garage, porticos, entryways, stairways, plazas and surrounding sidewalks.
Police alleged that the drone was being flown at a low altitude over members of the public and City Hall employees. The security officer told investigators he was concerned the drone could crash into the crowd and cause an injury.
The court records also alleged Webb removed his hands from the controller and diverted his attention from the drone while it was in flight. Those allegations formed part of the basis for the three criminal charges filed against him.
Monday’s trial centered in part on whether Webb could be convicted of trespassing when he did not physically enter the area covered by the order.
According to the Telegram, Beauchamp argued that Webb remained outside City Hall property and that operating the drone did not violate the no-trespass order. She also argued that drone operations are governed by the Federal Aviation Administration and that the state could not enforce federal aviation regulations.
Assistant District Attorney Jennifer Grieco argued that the FAA regulations were not the issue before the court and that Webb’s operation of the drone within the prohibited area constituted trespassing because the aircraft effectively became an extension of his physical presence, according to the Telegram.
Welsh agreed with the prosecution on the trespassing charge, finding that Webb controlled the drone’s movements and that it acted as an extension of him, the newspaper reported.
Despite receiving a sentence of 30 days, time served in the City Hall case, Webb remains in custody in connection with a separate pending case, according to the Telegram & Gazette.
That case stems from a June 15 incident at Polar Park, where authorities allege Webb flew a drone at low altitude over a closed police mass-casualty training exercise. Webb was charged with disorderly conduct and disturbing the peace.
Following that incident, a judge revoked Webb’s bail on other pending cases, allowing him to be held without bail for up to 90 days. The charges arising from the Polar Park incident remain pending.
The prosecution called three witnesses during Monday’s trial: Worcester City Solicitor Alexandra H. Kalkounis, Worcester police Officer Adam Sthay and City Hall security guard Aaron Gagne, according to the Telegram. Webb waived his right to a six-member jury, leaving Welsh to decide the case.
The Worcester Guardian has requested updated court records reflecting Monday’s trial, verdict and sentence, as well as city records related to the no-trespass order and comment from Attorney Beauchamp. This story will be updated as those records become available.
Have a story tip, community concern, or insight to share? Email Editor Charlene Arsenault at carsenault@theworcesterguardian.org.
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