Planning commission recommends revoking Milano’s entertainment permit after neighbor complaints

The Winchester Planning Commission voted on Nov. 18, 2025, to recommend that city council revoke the entertainment conditional use permit (CU09-198) for Milano Sports Bar at 107 West Boscawen Street following a public hearing that drew neighbors, business representatives and police staff.

Staff presented the revocation process and materials, noting the CUP granted in 2009 and the statutory ability to amend or revoke a CUP when conditions are not met. Planning staff said that, based on repeated citizen concerns and enforcement history, revocation was among the appropriate options to send as a recommendation to the council.

Police staff reviewed extra-patrol practices and call logs used in the staff packet. According to staff testimony, November call logs showed no calls for service documented inside the establishment and October included one possible drunk-in-public call on Oct. 21 that may have been outside the business; commissioners questioned whether recorded incidents originated inside the bar or in adjacent parking lots.

During public comment Milano’s counsel, Jonathan Sylvester, urged the commission to consider Milano’s 21-year history and recent management changes and submitted a five-point proposal to address community concerns. "The acts of the pictures he's given this board…are not supported by our bar," Sylvester said, calling attribution of off-site incidents to Milano’s patrons "speculative." New manager Brenna Hocht told the commission she had addressed reported issues since taking over and pledged to work with the city and police to resolve concerns: "We are more than happy to do anything that is within our power to cease any of that type of activity that we are able to." Several employees and security staff also testified they have tightened entry policies and coordination with police.

Residents and nearby property owners described recurring late-night noise, loitering, trash and public urination in the parking lot adjacent to Milano’s and urged stronger remedies. "I haven't slept in two and a half years," one resident said, describing repeated disturbance from motorcycles, idling cars and shouting near her bedroom window.

Commissioners debated options including a time-limited probation or amendments limiting live-entertainment days, but several commissioners concluded that Milano had failed to comply with multiple CUP conditions. Commissioner (speaker 11) moved that the Planning Commission recommend revocation of CU09-198, citing repeated noncompliance and insufficient mitigation of negative neighborhood impacts; following discussion the commission approved the recommendation and forwarded it to city council, which will make the final legal decision. Under the code, Milano may reapply for a CUP after one year, and any appeal from council would proceed to circuit court.

The commission’s action is advisory; the city council will consider the recommendation in a future meeting. The planning staff packet and submitted public comments were entered into the record.