Packed harbors, crowded ferries, maskless Main streets and indoor dining — after 15 months of pandemic lockdown, Martha’s Vineyard is readying for its first full Memorial Day reopening in two years, with state restrictions set to lift just as an unprecedented stream of visitors and seasonal residents are set to arrive.

Downtown Edgartown was bustling all week. — Ray Ewing

The double-barreled, shotgun start to the season has the aura of pre-pandemic times — a semblance of normalcy quickly settling in with a perfect storm of springtime activity. Dozens of restaurants are reopening or reinstating their regular hours. Military choppers are flying over Katama. Bars are bustling on Circuit avenue, and the Back Door Donuts line is snaking to Kennebec avenue.

On Memorial Day weekend 2020, Back Door Donuts didn’t even have its front door open.

But this is 2021. Nothing about it is normal.

Advance booking numbers from the Steamship Authority and interviews with harbor masters, rental agencies and Island businesses suggest the Island is shaping up to not just have a busy Memorial Day weekend, but a record-breaking one, with reservations in everything from harbors to houses blowing pre-pandemic rates out of the normally choppy Vineyard breakwater — a harbinger for the high summer season to come.

According to SSA prebookings for vehicles, the Vineyard route is up 50 per cent from 2020s slow Memorial Day weekend and 15 per cent from pre-pandemic 2019, with about 1,400 more vehicle trips already booked for Thursday through Tuesday. SSA spokesman Sean Driscoll said the numbers serve as a forecast for the rest of the season.

“This pattern that we’re seeing of this weekend of being about 20 per cent above 2019 is carrying through the summer,” Mr. Driscoll said. He added that reservations were still available — but on off-peak days like Wednesday afternoons. “If you want to go see the Red Sox, you can go to a game. But you’re not going to get Red Sox-Yankees tickets,” he quipped.

Harbors are seeing a similar unprecedented flood of business. Edgartown harbor master Charlie Blair said online reservations for the Fourth of July weekend sold out in under two minutes. The harbor opened the week before Memorial Day for the first time in its history. The weekend before that there were 50 boats in the water. Mr. Blair said he had never seen so many, so early.

“Just like Custer at Little Bighorn,” Mr. Blair said. “You can’t buy an outboard motor in North America. Every boat is sold. Everybody is going to come . . . It’s not going to be a quiet summer.”

Outdoor dining is a popular option. — Jeanna Shepard

Vacationers are not just planning to come by sea. Elizabeth Weedon, a spokesman for, which manages approximately 500 active rental listings on the Vineyard, said bookings were up 50 per cent overall from 2019 and 85 per cent between Memorial Day and June 25. The listing agency has created an entirely new directory to handle the frantic demand.

“Words like unprecedented come to mind — just the likes of which we have never seen in our 23 year history,” Ms. Weedon said. “[Renters] are so excited . . . I remember speaking to people who were practically in tears last year.”

Hotels are seeing longer average stays and historic booking rates as well. Jon McConnell, owner of the Vineyard Square hotel in Edgartown, said 2021 was set to surpass 2019 as the strongest booking season in his 12-year history. Harbor View Hotel general manager Scott Little said that the hotel was up 24 per cent from its prior seasonal booking record.

And with state capacity restrictions set to expire May 29, dozens of main street Vineyard retailers and eateries said they finally saw a light at the end of a long, dark, 15-month tunnel, hardly containing their excitement to reopen — and reopen fully.

“It feels like a different world this Memorial Day,” Molly Coogan, manager of the Bunch of Grapes Bookstore in Vineyard Haven said. “Last [Memorial Day] we had just reopened and things felt pretty scary and uncertain . . . and we didn’t know what our summer would look like. But this summer we feel pretty optimistic and hopeful. We really think people are going to be walking up and down Main street this year.”

But that, of course, begs its own questions.

Last year, as the pandemic quickly took hold, the Gazette published a comprehensive online directory of Island business hours titled “What’s Open, What’s Closed,” with most establishments falling in the latter category during Memorial Day weekend. Those that were open had their hours severely curtailed, only offering takeout or limited indoor dining.

This summer is different.

Main street Vineyard Haven is a different scene this year. — Mark Alan Lovewell

At least 15 restaurants in down-Island towns are open for Memorial Day that weren’t open in 2020, ranging from the MV Chowder Co. in Oak Bluffs, to Atria in Edgartown to Beach Road in Vineyard Haven. But with huge numbers of customers expected, and capacity limits lifted, all are still struggling with the Island’s sisyphean staffing shortage, wondering how they will serve the customers they’ve been counting on for months.

Laurie Welch, an owner and founding partner of Basics and Eastaway Clothing, said the company has been working with recruitment agencies to bring in foreign staff, without much success. Others can’t find staff at all.

“I wish there was more available housing. That’s the trickiest aspect of staffing,” said Scott Hershowitz, manager at Mocha Motts in Oak Bluffs.

Despite the severe employee shortage, nearly all retailers and restaurants welcomed the arrival of Memorial Day — especially those that didn’t get to shepherd in the season last year. For Louis Arias, manager at the Seafood Shanty in Edgartown, decreased concerns over Covid-19 have not only increased business, but also have made it easier to find willing employees. “There are more people wanting to do the job,” he said. “People were afraid to work last year.”

Last year at this time Eric Coles, co-owner of Lennox and Harvey in Vineyard Haven, had his store closed. This year, he’s focusing on pandemic-inspired inventory, like large canvas beach totes, cotton hoodies, serving trays and enamel wear for outdoor entertaining. He only noticed two empty storefronts on a once-ghostly Main street.

“We’re really excited to be open,” Mr. Coles said. “I quite love when the towns are all buzzing . . . It feels like the town is just coming back at the same time as the Island and the world.”

With Governor Baker lifting the required mask mandate this Saturday, May 29, store owners and managers will have the discretion to enforce indoor masking. But “enforce” felt like a strong word for most main street retailers.

“We are still going to be wearing masks . . . because there are still people out there who are nervous,” Chris Salvo, owner of Sanctuary in Oak Bluffs said. “But it will be difficult to accommodate everyone. We are just going to ask, but we are not going to enforce it.”

Wayne Iacono at the helm of Freedom. — Jeanna Shepard

Pete Campbell, manager at Ryan Family Amusements in Oak Bluffs, anticipates a “return to normal” as soon as the state allows it. “I expect that the plexiglass will come down on Saturday,” he said. “We are a place where people smile, and you can’t see that through a mask,” he added. “I’m excited to see those smiles return.”

And India Rose, owner of Sideline in Vineyard Haven, wants to celebrate. She opened her sporting goods line in November, after the pandemic summer, and plans to have a DJ in the store on Sunday while people shop.

“I do think that the combination of the mandate being lifted on the holiday weekend just makes it that much more for people to look forward to,” she said.

Even the traditional rites of Memorial Day are set to return. At a Tisbury selectman’s meeting Tuesday, town officials said the annual Memorial Day parade will march on, stepping off from the American Legion Hall at 10:30 a.m. Monday and continuing through the Oak Grove Cemetery.

Ironically, there appears to be only one thing that could cast a damper on a perfect Memorial Day weekend. Rain is in the forecast. And that might not be a bad thing.

“I’m a little happy about that,” Mr. Blair said. “Wind, rain, hail — maybe some snow. That would be helpful.”

Maia Coleman contributed reporting.