Memorial Day weekend has arrived on Martha’s Vineyard, bringing with it a mix of uncertainty and optimism as Islanders navigate the shifting political and economic climates. 

At the onset of the unofficial start to summer, more than a dozen business owners, hoteliers, and chamber of commerce officials said they have made adjustments for the season and continue to grapple with the rising cost of a vacation.

But they still expect brisk business this year buoyed by major events, including the 50th anniversary of the release of Jaws.

“I always feel optimistic going into the summer, despite the national climate of volatility and uncertainty,” said Luke DeBettencourt from his perch at the Corner Store in Oak Bluffs’ Healy Square. 

Jane Harmon, of Carousel Ice Cream Factory, is ready for the season.

Jeanna Shepard

Jane Harmon, of Carousel Ice Cream Factory, is ready for the season.

Jeanna Shepard

While the business community readies itself for the summer crowds, Islanders and visitors alike will also use the weekend to remember those who gave the greatest sacrifice. On Friday, the Island elementary schools participate in the annual March to the Sea tradition, with Oak Bluffs returning for the first time in several years.

The annual Memorial Day parade will march through Vineyard Haven on Monday, beginning at 10:30 a.m. at the American Legion Hall. Several groups including veterans, military personnel, scouts and the Women’s Auxiliary will join the parade.

Robert Tankard, the veterans outreach coordinator at Martha’s Vineyard Community Services, helped organize the parade and the March to the Sea event at the Oak Bluffs Elementary School.

“All those young men and women who served...a lot of them didn’t come home,” Mr. Tankard said. “What we’re doing on Memorial Day is remembering them. Remembering them for their service and respecting what they did. Those who have passed on and those who are still with us, we are thanking them.”

The forecast calls for stormy weather, with the possibility of events being rescheduled. Despite the wind and rain, Steamship Authority bookings for the holiday weekend are on par with last year. About 75 per cent of the vehicle reservations headed to the Island are booked, and about 61 per cent of the return spots are filled, according to Steamship spokesperson Sean Driscoll. 

Last year, 76 per cent of the Woods Hole to Martha’s Vineyard reservations were booked and 69 per cent of the returns were taken. 

Mr. Driscoll said the weather, potentially longer stays and the holiday weekend taking place earlier in the month could be reasons behind the slight decrease in reservations.

Opening day of vehicle reservations for the summer, which took place back in February, also showed some signs of a slight dip. The Steamship Authority had nearly 21,500 transactions on opening day, compared to about 23,700 the year prior.

Erin Tiernan has changed her stock to cater to different clientele.

Jeanna Shepard

Erin Tiernan has changed her stock to cater to different clientele.

Jeanna Shepard

“There are certainly some economic uncertainties that play into that,” Mr. Driscoll said. 

Still, he expects travel to remain strong as summer gets underway. 

“We had a strong opening to the season, I have no reason to expect it will be anything different this year,” he said.

The Island’s storefronts are looking polished and ready for the season, said Erica Ashton and Alessandra Hagerty, executive and deputy directors of the Martha’s Vineyard Chamber of Commerce. They described early bookings at hotels and strong seasonal hiring, signaling the summer is shaping up well.

But the two echoed the wary sentiments felt throughout the Island. They said there is uncertainty regarding the impact of increased tariffs put forth by President Donald Trump’s administration, which are anticipated to increase the cost of imported goods.

Ms. Ashton said many businesses are taking a wait-and-see approach.

“I think that people are tentative, knowing that we have a new administration in government and there have been some tariffs that could potentially affect tourism,” Ms. Ashton said.

Angela Sison, owner of Conrado in Vineyard Haven, said she has seen some of her products’ prices rise already due to tariffs. 

“We had a sock order two weeks ago and we didn’t realize that we had to pay more than what the socks were worth on tariffs alone so that was disheartening,” she said.

Annette Luna, co-owner of Dune and Boneyard Surf Shop in Edgartown, said she is getting emails daily from suppliers urging them to buy stock before the tariffs raise prices.

The Island’s hotels largely are not feeling direct impacts of increased tariffs. However, some are seeing regular visitors who hail from abroad hesitant to travel to the Island.

Corner Store owner Luke DeBettencourt is optimistic about the season.

Jeanna Shepard

Corner Store owner Luke DeBettencourt is optimistic about the season.

Jeanna Shepard

Susan Goldstein, owner of the Mansion House in Vineyard Haven which is celebrating its 40th anniversary this year, said she received feedback from repeat customers who won’t be returning.

“We’ve had really kind and sweet letters from repeat Canadian guests saying that although they love the Mansion House, they are reluctant to spend their vacation dollars in the U.S. due to our political climate,” she said.

When walking through downtown Edgartown, visitors may notice storefront vacancies. Main street has three empty stores and a few others are scattered throughout the town.

Erin Ready, executive director of the town’s board of trade, acknowledged that the vacancies on Main street are easily visible. She said some were left vacant when businesses moved to a better location within town, and others were already filled with new businesses over the winter.

She said the few that are still empty speak to high rents, a problem not unique to Edgartown. Ms. Ready said the board has been focusing recently on improving relationships with property owners and landlords.

“Rent prices have been consistently on the rise, and we’re facing a year when our business owners are taking a more thoughtful and cautious approach,” Ms. Ready said. 

Claudia Canerdy, who owns a jewelry shop on Main street nearby a vacant storefront, said while this can reflect poorly on the town, she doesn’t think it will affect tourist traffic.

“I’m not really worried about the results,” Ms. Canerdy said. “[Shoppers] are going to come to Edgartown anyway.”

Larger trends from recent years continue as the price point for visiting the Island increases.

Erin Tiernan, the co-owner of Eastaway and Basics Clothing Company and owner of the boutique Oso in Oak Bluffs, said that over the past several years, she has begun to add more expensive items to cater to tourists. 

Empty storefronts in Edgartown are awaiting new tenants.

Ray Ewing

Empty storefronts in Edgartown are awaiting new tenants.

Ray Ewing

“That’s a definite difference that we’ve seen,” she said. “The Vineyard has just gotten more expensive, so now the tourists that this place is attracting are looking for nicer items.”

Hugh Taylor, the owner of Outermost Inn in Aquinnah, feels similarly. The restaurant is anticipating the costs of base products to increase by 20 per cent, but he doesn’t plan to increase the cost to customers. He said his restaurant has been a destination location for patrons willing to pay more.

“We’re high price, so whoever comes in, they sort of bite the bullet,” Mr. Taylor said.

Overall, businesses said they still anticipate a successful summer.

At Lambert’s Cove Inn in West Tisbury, a popular wedding venue, owner Jon Saunders hasn’t seen dippings in reservations.

“We’re not seeing any effect at this point in terms of folks wanting to travel or wanting to still get married or book weddings for next year and the year after,” he said. 

Business owners are also preparing for tourists to return to their favorite summer habits. Molly Coogan, owner of Bunch of Grapes Bookstore in Vineyard Haven, has stocked up with reader favorites, including romance and fantasy genres. Jake Gifford, co-owner of Lazy Frog in Oak Bluffs, has loaded the shelves with fly ball and bucket golf for people looking for a game to play on the sand.

And the long-awaited Jaws 50th anniversary has already brought early bookings to hotels and early reservations at places hosting events. 

Mark Snider, owner of the Winnetu Oceanside Resort in Edgartown, said his hotel was fully booked before they announced their Jaws event in June.

Larkin Stallings, the president of the Oak Bluffs Association and owner of the Ritz Cafe, believes that the events surrounding the anniversary will help buffer any potential loss of tourism.

Despite obstacles, Elaine Barse sees the Island remaining a vacation destination.

Ray Ewing

Despite obstacles, Elaine Barse sees the Island remaining a vacation destination.

Ray Ewing

“I do believe in my heart of hearts that it is going to make up for whatever little we’re going to have lost from other tourism,” he said.

Elaine Barse, who has worked in retail for over three decades and owns The Green Room in Vineyard Haven, said that while different obstacles arise each season, the Island continues to be a vacation mainstay for many. 

“We’re insulated here, so that’s a good and a bad thing because people look to the Vineyard as their safe place, if you will,” she said. “They’re looking forward to some sort of feeling of normality.”