Updated April 2
Millions of dollars are on the line as the first few Vineyard towns to hold their annual town meetings prepare and need to convince voters to approve property tax hikes to meet rising costs.
Edgartown, Oak Bluffs, and West Tisbury are set to hold their annual town meetings on April 14, and each of them have overrides on their warrants to partially fund their operational budgets.
While overrides are not new on the Island, they’re usually utilized to fund specific projects or purchases, rather than for operational budgets. Towns are limited to collecting no more than 2.5 percent of property values in taxes by a state law called Proposition 2½. The state law also restricts property tax increases. But these restrictions can be bypassed if an override is approved by voters at town meetings and at elections, which are scheduled for West Tisbury, Oak Bluffs, and Edgartown on April 16.
Proposition 2½, enacted in 1980 in response to an outcry against rising property taxes, currently creates hurdles for towns finances. James Hagerty, Edgartown town administrator, told The Times that the state law doesn’t take into consideration cost-driving factors and inflation.
“It’s very difficult these days to stay within the constraints of Prop 2.5,” Hagerty said. While the town’s request of a $900,090 override for its more than $53 million budget isn’t the highest Edgartown has seen, Hagerty highlighted that this is the first time in a decade the town has asked for one to fund its budget.
And Edgartown isn’t even the largest override proposed so far. Oak Bluffs is requesting a $1.9 million override — the highest in more than 25 years — for its $46.2 million budget, and West Tisbury a $3.49 million override — the largest in the town’s history — to fund its $31.6 million budget. Local officials say there isn’t one single reason for the overrides, but a confluence of reasons including rising costs, school operations, insurance rates, cost-of-living adjustments for employees, and the surge of prices since the COVID-19 pandemic. All are factors that drove up budgets. Additionally, state funding hasn’t kept up with increased costs, and federal pandemic grants have dried up.
Aquinnah, Tisbury, and Chilmark will hold their town meetings at later dates — May 14, April 28, and April 27 respectively — and are still crunching numbers for their budgets and have yet to release final warrants as of Wednesday morning. But officials in all of these towns said they plan to present overrides to voters at their respective town meetings.
Overrides aren’t just happening on the Vineyard. The Boston Globe reported that record property tax hikes are being presented to voters statewide to meet rising costs. Some communities are considering where cuts may need to be made, like Marblehead’s possibility of closing its public library if it can’t fill its $7 million deficit.
There are concerns over what could happen if voters shoot down an override. And communities where residents tire of tax hikes have already felt this sting. Winchester failed to pass its record-breaking $11.5 million override at the polls on March 21, a result expected to possibly lead to layoffs and cuts to services.
Jennifer Rand, West Tisbury town administrator, highlighted during a March 25 West Tisbury Select Board meeting that there are parts of the budget that were “untouchable” and were required to be funded, such as a half-million dollars for state-mandated PFAS remediation because of contamination that stemmed from a town fire station and the closed landfill.
Rand underscored that it’ll be important to convince voters this isn’t just a “frivolous ask.”
“Departments, plural, will be gutted if the town has to find $3.5 million,” Rand said at town hall. Even if it’s uncertain where the cuts would be made, critical services could be impacted: “That’s not a threat. It’s a fact.”
Hagerty told The Times that his town’s budget had enough “redundancy,” but failing to pass the override would mean a significant budgetary reduction, and some expenses, like an additional firefighter or additions to Edgartown School, wouldn’t be feasible.
Oak Bluffs’ recently released town meeting book laid out what could happen if the override failed at either the town meeting or the election. Town officials highlighted that expense reductions would happen across all of its departments, and could result in the loss of some services. Any new positions, including a proposed school resource officer, would be eliminated, and a hiring freeze would occur.
But there are still avenues if an override fails. A select board could vote to hold a special town meeting to provide, as Hagerty described it, a “more surgical” budget. The town would still need to consider how to fill the financial gaps, and where to shave its expenses.
Some local officials are optimistic. Jessica Miller, West Tisbury Select Board member, said at her board meeting that she believes voters would understand the funding necessary for services they often utilize, such as the town library.
“I think the voters see us doing our best,” Miller said.
Towns are preparing estimations on how much a resident in town will pay, but not everyone will pay the same tax rate increase if overrides are approved. Edgartown has a single tax rate, but Oak Bluffs and West Tisbury have residential tax exemptions of 15 percent and 30 percent respectively. This means people who own second homes or other types of residential properties they don’t occupy, including apartments and vacant lands, in Oak Bluffs and West Tisbury will pay more.
“It’s really hard to calculate that until it passes,” Jennifer Smyth, Edgartown town accountant, said of the overrides.
Editor’s note: A previous version of this story misidentified Jennifer Smyth as the Oak Bluffs town accountant.

Overrides is a liberal euphemism for higher taxes. Don’t be fooled again. Town officials should live within their budgets. These same officials should reduce their salaries, cut all expenses by 20-30 percent rather than beg property owners to absorb more taxes.
“Eventually you run out of other peoples money”
Should we the people decide?
Cut Police salaries by 20-30%?
Are our town officials salaries above the average of other small towns in the State?
Above yours?
The Island has some of the lowest tax rates in the state.
This has been said for 40 years, but I don’t see any improvement. The concept of 6 towns is not working financially. Six of everything is such a waste. The Island only needs 1 police station, 1 elementary school, and 1 town government. I also think the Island needs to face reality and require those living here at least be legal residents. Undocumented residents cost tax payers millions each year, especially to our school budget, yet they often don’t contribute to the tax base. If you don’t take this into consideration you will be forced to leave, as your cost of living will become prohibitive.
We the people will decide how may police stations, and elementary schools we want.
Would you want it anyother way?
Should someone at the “Federal Level” decide?
How many Island residents are illegal?
How much have they cost the towns?
How many illegals work for native Islanders?