Greenport officials are considering parking passes for village residents and downtown employees following backlash over an expanded paid parking program — even as the village has yet to hire any enforcement officers.
The controversial metered parking issue took center stage at a meeting Thursday, where trustees discussed potential changes, including resident permits, employee passes and adjusted hours.
Village officials say the program is designed to ease seasonal traffic congestion, increase parking turnover in high-demand areas and generate revenue for needed road and sidewalk improvements. However, some downtown residents argue that the system unfairly requires them to pay visitor rates — $3.50 per hour — to park near their own homes.
“We rolled it out, so now it’s time to tweak it,” Trustee Mary Bess Phillips said.
But some questions from those in attendance quickly turned to how the system will be enforced. The village has yet to hire the two part-time parking enforcement officers approved in this year’s budget, and officials said they are still interviewing candidates for the positions.
Village officials did not provide a timeline for the hires when contacted by The Suffolk Times on Friday.
Southold Town police officers are actively writing tickets for those violating the new regulations.
But after outcry about the expanded meters — launched in a pilot program in the fall of 2024 on Main Street and Front Street — Treasurer Adam Brautigam said officials have been actively exploring alternatives for village residents and business owners.

“At this point, no final decisions have been made, and we are continuing to look at options,” he said. “However, I will say that the meetings were productive, and it appears there may be solutions available that could help the village implement a resident parking system while minimizing the administrative burden on staff.”
Deputy Mayor Patrick Brennan said the biggest complaint he’s heard is the hourly rate.
Mr. Brautigam said the initial rate was going to be $3.50 plus a surcharge. The village decided to absorb the surcharge, meaning for every hour, the village receives roughly $2.98, with the rest going to ParkMobile, the app managing the payments.
Trustee Lily Dougherty-Johnson said there is also a fear within the business community that people will stop coming downtown and that people will be less likely to open a business.
“We’re trying to get a revenue stream here, get tourists and visitors through the village,” Trustee Julia Robins said. “If that hurts the businesses somewhat, it’s kind of a catch-22.”
Newly-appointed Village Administrator Jenna Butler-Esposito poured cold water on ease after a suggestion to make downtown workers eligible for passes. She said it would require employers to send the village lists of all of their employees to verify they actually work there.
Mr. Brennan said he surveyed parking around the village before Thursday’s meeting and found that roughly two-thirds of street parking remains free, while about one-third is metered. He said the same breakdown appeared to apply to village lots.

“I think you’ve been doing a good job trying to communicate the new parking scheme, and there’s been a lot of anxiety,” Mr. Brennan said to Ms. Phillips, who’s been active on social media and in letters to the editor in The Suffolk Times since the rollout.
However, he said, “the people I talk to seem to often be somewhat relieved when they understand the hours, the seasonality of it.”
The board agreed that residents with mobility issues could use handicapped parking permits to park for free. Village counsel Jared Kasschau said any resident parking pass would likely need to be available to all village residents, not just those who live downtown.

The program added two newly metered parking lots this season — one off Main Street and another off Adams Street — operating daily from Memorial Day through Columbus Day from 9 a.m. to 9 p.m.
Paid parking was already in place on Front Street between Third and Main streets, as well as along Main Street from Center Street to the Claudio’s parking lot.
Greenport resident Bridget Elkin said she is in favor of paid parking when needed and offered some ideas on ways to soften the blow on residents. One, she said, was to potentially have the first half-hour or hour be free for everyone to “solve the problem of picking up takeout, or grabbing coffee without having to pay for a cup of coffee again.”
She said moving the paid times to begin at 10 a.m. could be beneficial “because the early morning is a lot of resident activity; getting coffee, pastries.”
It remains unclear when a formal proposal could come before the board. Mayor Stuessi asked if it would be practical for the board to put a resolution on parking passes on next week’s regular session agenda.
Ms. Butler-Esposito said, “No, not yet.”
The post Greenport considers parking passes amid paid parking backlash, enforcement questions appeared first on The Suffolk Times.
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