The seasonal ebb and flow of Island life moves like the tides, a motion that is necessary to keep the local community afloat. But these days, the summer economy and the need for affordable housing feel more like an unpredictable crosscurrent that threatens the sustainability of the Island.
Twenty thousand year-round Islanders live and work here in the winter, waiting for the waves of 100,000 people to wash up on local shores every summer.
There’s a complex and symbiotic relationship between year-round residents on Martha’s Vineyard and the summer boom. Seasonal workers and Islanders alike rely on the tourism-fueled summer economy, and yet the hordes that come increasingly threaten their very ability to stay here.
Now and historically, safe and affordable housing has been the biggest challenge in keeping the mutually beneficial relationship alive. While summer visitors and the workers needed to accommodate them aren’t a new phenomenon, this summer, that current feels like it is ripping. And business owners and the people they employ are becoming increasingly concerned.
This is the first in an ongoing series by The Times to navigate the places where a sustainable Island life meets a thriving economy, which, without fail, leads back to the issue of affordability and housing. The Times set out to catalog the reality of a summer economy on a finite piece of land, including lodging for the people who live here and the people who visit.
Over the past 11 months, The Times has looked at historic records and books, and interviewed housing and town officials, small business owners, and workers. Tours of some accommodations for seasonal employees have painted a picture of a place strained for space, and tenants with nowhere else to turn.
The data alone paint a bleak picture of housing on Martha’s Vineyard. For Islanders who are able to find a place to stay, nearly half spend more than 50 percent of their income each month on their rent or mortgage, which is double that of those renting and owning in Greater Boston. Calculations by the Martha’s Vineyard Commission (MVC) from 2025 showed that a person earning $168,615 a year, far higher than the average Vineyarder, could not afford to buy a home. And at an estimated $3,000 rent for one room and one bath and a minimum wage of $15 per hour, the numbers don’t come close to doable for most local workers, even to rent.
Meanwhile, 60 percent of the housing stock on the Island is considered vacant, or lived in for fewer than two months out of the year. Those seasonal homeowners rarely rent out to year-rounders. Islanders and local businesses increasingly feel the squeeze of low availability, even when the houses are physically there.
The exacerbated dynamics Islanders see playing out now are all part of an ancient rhythm.
Arthur Railton, the longtime editor of the quarterly Dukes County Intelligencer, wrote in his 2006 book “The History of Martha’s Vineyard: How We Got to Where We Are” that summer visitors had been coming to this landscape since the beginning of recorded time.
He explained, “They roamed over its hills and valleys more than 10,000 years ago. But they hadn’t come to vacation at the beach; there was no beach.”
Martha’s Vineyard wasn’t yet an island, all those millennia ago, Railton writes, and the “summer people” were hunters who purposefully migrated to the land to hunt animals for sustenance. Now, these seasonal visitors look a bit different, and they are after a different game: Airbnb deals, affordable rental homes, and ferry reservations.
Jumping to modern history, by 1860, locals saw the positing of the Island as a massive vacation destination. The mid-1800s boom was partly due to camp meetings in Oak Bluffs that gained national attention, and partly an effort from Islanders to make downtown more attractive through building resorts and hotels. When they built it, visitors came. But they needed seasonal workers badly.
“There’s a strong parallel between 19th century seasonal labor and 21st century seasonal labor,” Martha’s Vineyard Museum’s research librarian, Bow Van Riper, said.
He said details are rather scarce, but immigrants, people of color, and Wampanoag tribe members made up a large portion of hospitality workers over a hundred years ago, and were often put up in “the kinds of tenement-style housing you hear about” today.
Much has changed in the past 150 years. But some things have remained true. Housing accommodations have been amended, albeit sometimes questionably, for seasonal workers since the beginning of the Island’s foray into a summer destination in the late 19th century; the outsourcing from off-Island for local work is still a common practice.
This was somewhat easier when, in the 1970s and ’80s, the Island was a hot spot for a college student to come and work for that classic summertime job as a line cook, house painter, or lifeguard. Young people often stayed in family homes or rented a house with a group. Rent was then more affordable and could be split.
Susanna Sturgis, writer and longtime Islander, moved to the Vineyard around that time, and witnessed many of the changes that led to intense hikes in both population and cost. She saw the ways people rose to meet a Vineyard that was rapidly gaining popularity. But one visit to the Island in 1993 changed everything: a summer vacation by former President Bill Clinton with his family and the full White House entourage.
“I see the Clinton visit as being a turning point, because it really directed more attention on the Vineyard from people who hadn’t had a previous interest in the Vineyard,” Sturgis said.
As the summer population rose, so too did housing costs. Islanders started the dance of the “Island shuffle,” moving from the comfort of their home to other apartments, backyard shacks, or tents in order to make space for tourists and Airbnb rentals, or found other creative ways to stay on the Island, like building yurts or structures on their friends’ land. Tent communities even began to spring up in the warmer months.
As costs became more untenable in the ’90s and 2000s, Sturgis said people started to commute from the mainland.
Between 1970 and 1980, the number of year-rounders increased by 45 percent, according to the U.S. Census and MVC, to 8,897 residents. There were 8,700 housing units on the Island, and homes ranged from around $250,000 to $500,000 to purchase in 1980.
In the 1990s, summer rentals took off. The year-round vacancy rate was about 58 percent, nearly at the current standing this year of 60 percent, news outlets reported.
By 2000, the year-round population surged to 14,901, and a building boom equated to a total 16,621 housing units, according to data from the MVC. Many of those properties were built and bought by wealthy seasonal visitors who had a newfound interest in what the Island had to offer.
But part of what brought them to the Island was the people who lived there: the exact community who now can’t afford to stay.
Thousands of dollars are needed to rent a one-bedroom, one-bath apartment on the Island, and the current minimum wage can’t compensate for that. Many jobs on the Island have compensated for the higher costs here by raising that minimum, but in the hospitality industry, $15 per hour is a standard starting pay. Servers and bartenders at restaurants make far more money through tips, but their hourly rate is usually much lower, $6.75 or less. Year-round, however, those tips to compensate for the low starting wage are less reliable.
“Housing is the biggest issue that we face,” owner of S&S Kitchenette Spring Sheldon told The Times. She said multiple prospective employees have inquired about a job at her restaurant, but they all need accommodation, and she, like so many employers on the Island, said she just isn’t able to provide it.
And, as she pointed out, the housing crisis is just as hard for business owners themselves who often scramble to balance it all. “If this summer is quieter … you’re still having to pay rent year-round. Eventually, it’s going to crumble. If we don’t have a stable local community of people who have expendable incomes of their own, then the businesses that are here and exist will struggle more,” Sheldon said.
Fortunately for business owners, Island officials expect this to be a busy summer season. Erica Ashton, executive director of the Martha’s Vineyard Chamber of Commerce, said bookings at Cape Air are surpassing last year.
“This weekend feels like a turning point. With the weather improving, it’s shaping up to be one of the first strong retail weekends, and that energy is critical for our local businesses.” Ashton said about the first weekend in May.
A busy summer season, as welcome as that is, doesn’t change the problems that the Island increasingly faces every year.
And most business owners who spoke with The Times feel the same way as Sheldon: Finding workers hinges on housing; rentals are too expensive; and meeting the demand for tourism is more difficult as a result. The seasonal crunch of the Island spans many generations, but with a busy season likely around the corner, and affordability at its most dire point yet, the tipping point may be closer than anyone would like to admit.
“There’s no question that the Island needs the staffing, and we have insanely limited housing,” said Larkin Stallings, owner of the Ritz Café and president of the Oak Bluffs Association.
Stallings said he’s watched his employees grapple with rental issues over the 12 years he has owned the Ritz. Prices simply keep rising, and rental housing is increasingly limited.
Although there are many businesses that hire locals who have accommodations already, rarely does this make up the entire workforce. But Seth Woods, the owner of the Homeport restaurant in Menemsha, said he still hires high school and college students, and many of his employees have worked there for years, and are lucky enough to stay in family homes for the summer. He feels the effects of seasonality, but said “word of mouth is our best advertising” when it comes to hiring.
“Owning a year-round business is a lot easier to make ends meet than a seasonal one, as you can imagine. However, when you have a great crew, like we do at the Homeport, it makes things much easier,” Woods said.
With a squeezed job market nationally, many younger Americans have opted for internships that further their career, while others have turned to social media and remote work as a potential source of income. The number of U.S.-born students who are seeking hospitality jobs has simply decreased across the country, according to reports.
To compensate, one solution Vineyard businesses have utilized in the past few decades is hiring international students through a special work visa program known as the J-1 process. According to the U.S. State Department, the J-1 program brought 650 young international students to work on the Island in 2025, which The Times will unpack in the next part of this series.
Ewell Hopkins, former chair of the Oak Bluffs planning board, said there are some key questions that the Island community needs to answer: “Should we make this community easier to live in for a broad spectrum of people, or should we expect that there’s going to be a large percentage of migratory workers who can’t afford to live here who will be imported on a regular basis to do the work that needs to be done? What kind of community do we want?”
This is part of a continuing series by Sarah Shaw Dawson, The Times’ Island Writer, whose reporting beat is housing, health, and education.