The Sun Dog clothing store on Main street in Edgartown has a simple door sign: “Open seven days. Year-round.”

But while more Island businesses are choosing to remain open year-round despite the winter’s long chill, it is not always simple.

Their reasons for staying open differ, but all include a degree of community service, the benefits of expanded name recognition and the desire to attract and to keep an experienced and stable workforce that maximizes their summer business.

No one expects to make money on the Island in the winter. Breaking even would be terrific, most say.

C. B. Stark is one of the doyennes of wintering over. The jewelry store on Main street in Vineyard Haven has been open for 41 consecutive winters.

Cheryl Stark and her life and business partner Margie Meltzer have carefully attracted a dedicated staff that even allows the partners several winter months off while still serving the community.

“In addition to Jennifer Foxlee, our jeweler Jeff Regan and Sarah York, the store manager, commute daily from the mainland. Karen Whitely commutes every other week in winter, then manages our Edgartown store in the summer,” Ms. Stark said.

Around the block, Tilton’s Market, a specialty food business, opened last fall as a year-round business.

“The holidays were fantastic for us. We’re going to close for some refurbishing in January but [then] we’re planning to stick it out and see what the winter brings,” said Tania Tilton Clancy, co-owner with sister Kathleen Tilton Scobie.

The Tilton holiday business story is shared by other businesses who report that the season is lengthening. More businesses are open through the holidays and have an eight or nine-month season.

“It’s not like it used to be when I was a kid. Everything closed at Labor Day,” said Meredith Gallo, co-owner of Mocha Mott’s, which fires up hot soup every day in winter. Having a kitchen also provides heat for the restaurant, saving on energy bills, Ms. Gallo said.

In addition to providing reliable career employment, the Mocha Mott’s winter recipe blends pragmatism with community interest.

“People need their coffee,” Ms. Gallo said. “We are part of their daily routine. If we aren’t here they’ll go elsewhere. It’s an important time for us too. We’re here and we get to try different things, look at new ideas for the summer season.”

Veteran winter retailers and fledglings alike take deliberate steps to nurture their winter business.

For C.B. Stark, that means developing an Internet business and offering cleaning and resetting services. For Che’s Lounge coffeehouse down the street, co-owner J.P.Woodford looks for collaboration with other businesses. Che’s Lounge often offers music in its distinctly Cambridge coffeehouse ambience and has tied in with Vineyard Haven’s movie and theatre venues for pre and post-performance events.

“We’ve done some of that. We need to do more,” Mr. Woodford said.

He adds: “Vineyard Haven has lost its soul. We’re trying to revive it. “Wintertide (a former coffeehouse at Five Corners) used to do that.”

Che’s is a partnership between Mr. Woodford and Daniele Dominick, owner of the Scottish Bakehouse in Tisbury, which provides Che’s baked goods and helps both businesses manage inventory in winter. Che’s Lounge’s debut coffee mugs will be available later this month.

Whether visionaries or idealists, year-round businesses report some early indications of retiring baby boomers making their presence felt.

“I’m seeing some of that. Resetting jewelry for one generation to pass on to the next,” Ms. Stark said.

The business community in Oak Bluffs has worked at expanding its base of year-round business. Trader Jack’s, a Circuit avenue store, is a new entrant. Sharky’s, now a late-night (12:30 a.m.) year-round Island restaurant option, disclosed plans this week via text message to open a second location in Edgartown on May 1 on Upper Main street in the commercial development next to Donaroma’s nursery. The Edgartown location will be open at least through the fall, according to the announcement.

A generation of downtown business change has significantly affected Vineyard Haven and Edgartown over the past two decades.

Edgartown’s magnet businesses moved to the outskirts and to the retail triangle on the Edgartown-Vineyard Haven Road years ago. Now few downtown businesses are open in winter.

Renovation of the Harbor View Hotel and Resort may bring more convention business in the off-season, however. Also, two Edgartown restaurants, Detente and the Main Street Diner, recently took year-round licenses, according to Karen Fuller, administrative assistant to the selectmen.

In Vineyard Haven, a 2007 winter business entry, The Daily Grind, on Beach Road in Vineyard Haven, is in process of being sold by owner Paul Hakala to Sam Dunn, who reportedly plans a restaurant expansion.

Also in Vineyard Haven, the Capawock theatre’s reopening in 2007 brings some winter people downtown at night. Among new businesses, the Devil’s Dictionary has a smoking and pool room open several nights a week. Zephrus restaurant and Bunch of Grapes Bookstore provide other early evening diversions, along with Che’s Lounge.

Year-round businesses work hard to attract Islanders, who many winter retailers say encourage them but don’t always spend money to support them.

Mr. Woodford is more philosophical. “Islanders love to hibernate in winter. It’ll take some time,” he said.