Cocktail Mary Reopens Amid Debate Over Decades-Old Entertainment Buffer Rule

PORTLAND — The doors of Cocktail Mary swung open again in May, welcoming back patrons to the queer bar that relocated to the top floor of Oun Lido's on Market Street. Yet behind the celebration lies a broader struggle over Portland's downtown entertainment landscape, as city leaders grapple with a regulation that some argue has become obsolete and others view as essential protection for residents.

Owner Isaac MacDougal returned to Market Street after moving his establishment earlier this year, seeking a larger space designed specifically for a bar and nightclub. His journey began with a simple relocation—from a previous location to the historic Old Port district—but it quickly ran into a regulatory wall that may have cost him valuable time and opportunity.

The obstacle is a 100-foot entertainment buffer rule established during the 1990s and codified within the downtown entertainment overlay zone created in 2007. The regulation requires businesses to maintain a minimum distance from each other to prevent the overconcentration of nightlife establishments in the Old Port. For MacDougal, the rule proved particularly problematic. After signing his lease at 30 Market Street, he discovered he was too close to two existing licensed venues—Lincoln's at 31 Market Street and another establishment at 36 Market Street—to operate under current restrictions.

"The 100-foot buffer is working against us," MacDougal told reporters. "This ordinance keeps usable space dark for zero benefit."

The argument for reform comes primarily from local business owners who contend that the rule has stifled economic development and made it increasingly difficult to attract customers through special events. During a recent Housing and Economic Development Committee meeting, MacDougal testified that while the city continues to address vacant commercial spaces, the buffer remains a barrier to growth.

"We're trying to fill empty storefronts and revitalize parts of the downtown that feel lacking," said MacDougal. "But this rule keeps usable space dark for zero benefit."

Not everyone shares this perspective. Arcadia owner Dave Aceto, who is simultaneously developing a new bar called Bad Neighbors on Congress Street, argued that the buffer has become outdated and counterproductive. Speaking at the committee meeting, Aceto noted that twenty years is a long time to maintain policies designed for a different era.

"This ordinance keeps usable space dark for zero benefit," he echoed MacDougal's sentiment, adding that the rule appears to work against the city's efforts to fill vacant commercial real estate.

The proposal to eliminate the buffer has gained momentum. Councilor Wes Pelletier introduced the measure during a November meeting alongside a separate proposal to establish a 750-foot buffer between large entertainment venues—a move tied to controversy surrounding the proposed Portland Music Hall project. While the committee initially declined to advance the larger buffer proposal, it signaled growing support for reducing barriers to nightlife.

Pelletier framed the issue as one of creative freedom and artistic opportunity. "I want to create as many opportunities for the arts as possible, and create less red tape for businesses so they can bring artists in," he explained. "Removing the 100-foot rule could spread out the impact of entertainment activities by freeing up more area where nightlife can occur."

However, not all stakeholders agree that immediate action is warranted. Councilor Sarah Michniewicz acknowledged the potential benefits of loosening the rule but urged caution. "We need to do our homework about it," she stated. "The police department doesn't have as many officers in the Old Port as it did twenty years ago, and handling complaints could be more difficult if we reduce enforcement capacity."

The tension extends beyond policy debates into specific community initiatives. Dinah Minot, executive director of Creative Portland, described how her organization's "Third Wednesdays" events—featuring live music in the 511 Congress Street plaza—were denied approval by the city after securing cooperation from neighboring businesses. The permit was ultimately revoked by municipal authorities citing the entertainment buffer restriction.

For MacDougal, the timing matters significantly. Cocktail Mary had planned extensive programming throughout the summer, including DJ sets and drag queen performances. With the rule potentially still in effect, he expressed concern that the window for implementing these events may have closed by winter.

"The rule might change in time for the fall season," MacDougal said. "By winter, it could be too late."

The path forward involves further deliberation. The Housing and Economic Development Committee plans to host a workshop and public hearing, after which the planning board will submit a recommendation to the full council by early fall. Whether the buffer will be eliminated entirely or modified remains uncertain, but the debate highlights a fundamental question facing Portland's downtown: how to balance the desire for vibrant nightlife with the legitimate concerns of residents living among bars and clubs.

As Cocktail Mary prepares for its next chapter, the city watches closely to see if old regulations can be rewritten—or if the spirit of the law will continue to shape the character of the Old Port for years to come.