Island Theatre and Override Top Oak Bluffs Town Meeting

A general override, an historic property acquisition and several new bylaws are on the warrant for Oak Bluffs town meeting on Tuesday, April 14.

With more than 80 articles across back-to-back special and annual town meetings, Oak Bluffs residents will vote on the year’s $46 million budget, as well as new regulations for short-term rentals, large events and dilapidated properties. Residents will also cast ballot votes on the override and three debt exclusions.

Despite the warrant’s heft, assistant town administrator Wendy Brough is hopeful that town meeting can be wrapped up in a single night, but she didn’t rule out the possibility of a two-night affair.

“There’s a lot of bylaw changes in there, so I think that’s going to create a lot of discussion,” she said.

Topping the list of items for consideration next week is a $1.9 million general override, which asks to raise property taxes to support the town’s basic operational costs.

Under state law, municipalities are only allowed to raise property taxes by 2.5 per cent each year, unless they get special permission from the voters at town meeting and then again at an election. It’s a process many towns across the Vineyard and the commonwealth are undertaking as costs soar due to inflation.

Town administrator Deborah Potter said that rising costs across all areas have far outpaced the 2.5 per cent cap.

“The costs associated with [operating budgets] across Massachusetts have been increasing 8 to 10 per cent,” she said.

If passed, the override is projected to increase property taxes by $300 per year on a $1 million property.

The town is also asking for up to $5 million in a debt exclusion to either purchase or take by eminent domain the Island Theatre, the historic building at the head of Circuit avenue that has sat vacant since 2012. The building is showing signs of disrepair, and a board of survey previously declared it a safety hazard — issues select board members have said require action.

“We always hoped that the owners would do something with it, in particular at least take it down or dress it up in the interim [while] waiting for wastewater,” select board chair Dion Alley previously wrote to the Gazette. “Since that has not happened, one of the jobs of the select board is to represent the voters.”

Ms. Potter said there has been no further discussion of the item by the board since the owners, Ben Hall Jr. and Brian Hall, approached the board last month to request the board remove the item from the warrant. She added that if the article passes, the board will be able to decide how to proceed with acquiring the property, including deciding an intended use. The town’s projected tax increase if the debt exclusion passes is $59 per year for a $1 million property.

“[The article passing] doesn’t mean the town races out and gets $5 million and sticks it in their bank account,” Ms. Potter said. “What that does is gives us a mechanism by which borrowing can occur in order to facilitate these discussions.”

The town is also looking to proceed with an easement on the East Chop boat launch officially granting the town use of the property.

According to Ms. Potter, the article seeks to settle an ownership dispute over the East Chop boat launch, for which there are competing deeds giving ownership to the town and a private family. The town has long been maintaining the property and wants to ensure it’s available for public use, she said.

“We have been in negotiation with [the owners] to try to come to some sort of continuing arrangement with the existing use, because the town has been maintaining that area for upwards of 50 years,” she said.

“All of the indications have been that everybody is amenable to the easement as a permanent solution,” she added.

Voters will have the chance to decide if they want the tree warden, whose position is currently elected, to instead be appointed by the town.

“For the tree warden, that position has basically been held by our highway superintendent for years anyway… so it makes more sense to just wrap it into the job description of the highway superintendent,” Ms. Potter said.

Voters will also decide whether or not to make the town clerk position appointed instead of elected, as it is currently.

“I know that’s a much more emotional decision,” she said.

Ms. Potter said a state financial management review board recommended the change. For her, a benefit of the change is that it will allow the town to retain the services of a town clerk even if that person moves out of Oak Bluffs, currently an impossibility since it’s an elected position. She added that the town clerk’s technical responsibilities are growing and it’s important that the town be able to handpick a qualified applicant.

“With an appointed role, you can set basic minimum standards to ensure that you’re getting the most competent and qualified individual in that role,” she said.

But for select board member Mark Leonard, the proposed changes to the tree warden and town clerk roles threaten to undermine the democratic process.

“It really takes away the direct representation that voters have, because they vote for those people,” he said. 

Voters will decide whether to establish a new wastewater fund, which Ms. Potter said will act as a “savings account” to help ease the burden of unforeseen wastewater management costs. 

While not directly related to the town’s ongoing multi-step plan to significantly increase municipal wastewater capacity, Ms. Potter said the fund could safeguard the wastewater commission’s ability to react to needs related to the project.

“They could start putting away amounts of money out of their retained earnings for future use against other projects that might create an imbalance in the budget,” she said. “[We’re] not just trying to solve a today issue, but to solve future issues that we know are coming, but we don’t exactly know when.”

The town is asking for a $1 million debt exclusion to fund maintenance on the Dukes County avenue pump station. Voters previously approved $1.5 million to go toward the project, but tariffs from the Trump administration led to unforeseen costs, Ms. Potter said. The tax impact will be an increase of roughly $10 per year for a $1 million property.

“The pump station is critical to the infrastructure, especially along the camp meeting grounds, and because it pumps the wastewater from those areas to the wastewater treatment plant,” Ms. Potter said.

As it currently sits, the pump gets easily overwhelmed by flooding. Officials hope elevating the pump will help mitigate the impact of flooding and sea level rise on its regular functions.

Another debt exclusion asks for $825,000 to fund the design for the Lagoon Pond Watershed sewer extension, which ultimately aims to mitigate the pond’s nitrogen load. This effort is part of the town’s comprehensive wastewater management plan and would increase the property tax on a $1 million home by roughly $20 annually for the length of the project.

Ms. Potter emphasized that amount would fund the initial steps of the project but not the project itself.

“That’s [for] design and engineering,” she said. “It’s not the actual cost of the project.”

New regulations for short-term rentals are also on the docket.

A proposed new bylaw sponsored by the planning board’s zoning reform subcommittee would require registration of short-term rental properties with the town and would require that owners reside in their properties for at least 30 days a year. Additionally, it would prevent a single owner from operating more than one short-term rental, angling to block large companies from buying up the town’s housing stock.

At a planning board meeting in December, vice chair Chris Chambers said the bylaw has potential to protect residents’ right to rent their property while also safeguarding year-round housing and mitigating legal action related to short-term rentals. He mentioned recent lawsuits on Nantucket dinging the town and property owners for allowing short-term rentals when not explicitly permitted in town bylaws.

“We’re already delinquent on this,” Mr. Chambers said at the December meeting. “All it takes is for one person to have an issue and all our short-term rentals vaporize.”

Mr. Alley worries that existing short-term rental properties in Oak Bluffs could be harmed if the bylaw passes.

“I am concerned it would impact our current renters that were developed and funded under a different set of guidelines,” he wrote to the Gazette. “If this was in place today, they may not have developed at all.”

Another potential new bylaw would restrict large events at residential properties by asking that property owners planning events of over 50 people come before the select board to request a permit. The bylaw has exemptions, including family events such as birthday parties and graduation parties.

The bylaw as written says that the select board may deny a permit if an event is “deemed likely to be detrimental to the peaceful enjoyment of properties in the neighborhood.” It also notes that events intending to sell alcohol or food, as well as events that require an admissions charge or membership, will not be permitted.

Mr. Leonard said that constant major events in residential neighborhoods puts stress on town infrastructure in a way that can become dangerous.

“We had an incident where an ambulance and a fire truck couldn’t get down the road because there was so much traffic,” he said. “It becomes a public safety issue.”

Mr. Leonard acknowledged that he’s aware of a specific property on East Chop that has sparked complaints from neighbors, but he was adamant that the bylaw is designed to protect the town as a whole.

“We’re not targeting anybody,” he said. “That one property, it will apply to them, but it’s not because of them. It’s to support Oak Bluffs and make it a safer and better place.”

At a meeting last month, select board member Sean DeBettencourt expressed concern about the scope of the bylaw, which gives the select board jurisdiction over events “including but not limited to reunions, speaker events, retreats, and similar occasions.” 

“I’m super nervous about the implications,” he said. ”It feels like we’re inviting a lawsuit.”

A new beautification bylaw aims to help the town crack down on blighted properties, of which there are several in Oak Bluffs. If the bylaw passes, vacant properties will need to be registered with the town, and owners will be hit with daily fines if their buildings fall into significant disrepair.

“It’s important, because we do have properties in Oak Bluffs that seem to be let go, whether they’re abandoned or have multiple vehicles or are overgrown,” Mr. Leonard said. “It’s a way to keep Oak Bluffs clean and looking presentable and a place that everybody can be proud of.”

Ms. Potter and Ms. Brough encouraged Oak Bluffs residents to attend town meeting, as well as a public forum at 10 a.m. on Saturday, April 11 at town hall to discuss the budget vote and override vote.

“We want to explain [the budget and override] to the taxpayers, assure them that we do have their best interests at heart, and encourage them to show up,” Ms. Brough said.

Mr. Alley, who has seen a decline in voter participation at town meeting over the years, also encouraged attendance. He also emphasized that, though the select board oversees the process, the outcome of each decision is up to the people.

“We allow our voters to decide how they want us to handle these issues,” he wrote.

Oak Bluffs town meeting takes place at 7 p.m. on Tuesday, April 14 at the Martha’s Vineyard Regional High School performing arts center. The Oak Bluffs town election takes place on Thursday, April 16 from 10 a.m. to 7 p.m. at the Oak Bluffs Public Library.

This article appears in April 10, 2026.