Shifting population trends and the ongoing pandemic continue to redefine main streets on Martha’s Vineyard, even as the relative quiet of the off-season settles over the Island.

And with a strong summer now squarely in the rear view mirror, businesses in the three down-Island towns are gearing up for the launch of the holiday shopping season.

Interviews with more than a dozen brick-and-mortar merchants in Edgartown, Oak Bluffs and Vineyard Haven — from seasoned retailers to freshmen startups — revealed an upbeat outlook for the lean winter months ahead, as the traditional boom-and-bust cycles of a resort economy begin to stretch and flatten. But it all comes against a backdrop of deep fatigue after a challenging year with short staffing, global supply chain disruptions and restrictions such as mask mandates to protect public health.

At the moment many are working solo.

“Shop owners are doing it on their own. Since Oct. 1 it’s been [just] me. That’s the refrain you hear from everyone,” said Roni Hennessey, the owner of Sole, an Edgartown shoe store.

Christina Robinson of Chowder Company. — Jeanna Shepard

Kate Walpole, who owns Katydid in Edgartown, agreed. “It’s quiet now, but it was a fantastic season,” she said. “It’s quiet . . . [but] I can deal with it. And then I don’t have to pay anyone, right? Just pay myself.”

In Oak Bluffs some Circuit avenue mainstays like Mocha Motts and the Corner Store are closed. But for the businesses that remain open, the return to a slower pace is welcome.

“It’s actually very cool,” said Larkin Stallings, who owns the Ritz Cafe. “The folks that we’ve known for years come to patronize. We like to see them.”

He said it also gives him and his employees a breather after what he called the best summer in his six years of owning the popular tavern.

Newton Waite, co-owner of Vineyard Caribbean Cuisine, echoed the theme.

“They can come here now without having to fight for a parking spot,” he said, speaking of his late fall and early winter customers.

Enjoying a bite at Waterside Market in Vineyard Haven. — Ray Ewing

Downtown business owners in Vineyard Haven said they too are short on help, although year-round businesses such as CB Stark jewelers and Bunch of Grapes Bookstore are less reliant on seasonal staff.

“We’re lucky. I’ve got great year-round staff,” said Sarah York, who is manager at C.B. Stark and president of the Vineyard Haven Business Association. “Smaller businesses this time of year can run on a couple of people, but it depends on what you do,” Ms. York said. “Restaurants still need the same staff.”

Shoulder seasons are getting longer, most business owners said.

“Our shoulder seasons in the last four or five years have been pushing out,” Ms. York said. As a high-end jeweler, she said C.B. Stark is seeing shoppers with money they might have spent elsewhere if not for the pandemic.

“People aren’t traveling. People aren’t spending money on food. So they have disposable income,” she said. “There’s a lot of self-purchasing.”

Customers are also bringing in an unprecedented amount of broken jewelry, leading to a bottleneck in the shop’s repair department. “We’ve never experienced anything like this,” Ms. York said. “We’re promising two and three months out.”

Leslie Sterns at Bryn Walker. — Ray Ewing

The shoulder season shift has been noticeable to Stefanie Wolf, owner of Stefanie Wolf Designs on Circuit avenue. “It’s just a different crowd,” she said.

Ms. Wolf, who relocated her business from Edgartown to Oak Bluffs this year, also noted a distinct difference in the off-season patterns between the neighboring towns.

“In Oak Bluffs [the dropoff comes] when the ferries stop running,” she said. “In Edgartown, it used to be more of a gradual slide.”

Meanwhile, as they prepared for Black Friday and the return of traditional holiday lineups including the Christmas in Edgartown weekend (Dec. 9-12), tree lighting in Oak Bluffs (Dec. 1), and Thursday night shopping in Vineyard Haven (Dec. 9 and Dec. 16), down-Island merchants say they are seeing renewed interest in shopping locally.

“I just keep hearing over and over again that people want to do that this year,” said Jake Gifford, longtime owner of the Lazy Frog in Oak Bluffs.

“I love to do my Christmas shopping here and I may be a little bit biased toward small businesses but I just think that it’s easy,” said Ms. Hennessey. “You can’t beat the customer service . . . for exchanges and whatever.”

Erin Gosson at Basics. — Jeanna Shepard

She said many places plan to keep extended hours in December.

“Retailers that I have spoken to . . . most people have said to me that they plan for December to be open every day or a part of every day, so it will be nice. Between Vineyard Haven, Oak Bluffs and Edgartown we might give people options,” Ms. Hennessy said. She added: “Everybody is thrilled that Christmas in Edgartown will be returning . . . I think it’s really going to be great to have a happy event . . . I think we all need some happiness in our lives.”

Julia Tarka, owner of Rosewater Market and Takeaway and vice president of the Edgartown Board of Trade, said supporting local business is the point of the festive weekend.

“Our purpose is to support a sustainable local economy here in Edgartown, and we work to do that year round,” Ms. Tarka said, speaking about the board of trade. “Events like Christmas in Edgartown are designed to help remind Islanders and visitors that they can support their local economy here around the holiday season . . . and that helps everyone be open in the summer.”

Christmas shopping is already under way at the Bunch of Grapes in Vineyard Haven, where festive window dressings and holiday books remind passers-by that it will soon be gift-giving season.

“I think people have gotten the message of shopping early and shopping locally,” said longtime store manager Molly Coogan. By coincidence, Ms. Coogan said the store had rearranged its fixtures just before the pandemic, providing more space between shelves for comfortable browsing. Comfortable reading is also in demand, she said, amid the uncertainties of the Covid era.

Longer shoulder seasons have business owners more upbeat this year. — Ray Ewing

“People are looking . . . for things that are a little lighter. They want something uplifting,” she said.

And after the holidays? Many business owners said they plan to keep the lights on.

Ms. Wolf said she will spend time on development, designing jewelry and restocking gems and beads.

“The winter is usually a season to regroup,” she said. “This winter I can actually plan to have the retail store.”

Sarah Aliberti, co-owner of Summer Shades in Edgartown, concurred.

“I’m excited to start really building our website and this is a good reminder for me to really focus on that because we always have such great inventory. So it’d be nice just to keep things going,” she said.

Mr. Stallings at the Ritz called it the best season.

“This is my favorite time of the year, really,” he said.

More pictures.