Vineyard Haven is a place where people use benches as year-round communication centers. The curved wooden bench in front of Leslie’s Drug Store is one such center, and useful for gathering local intelligence.

“Art Buchwald once wrote in his national column that Leslie’s Drug Store was the place to learn what’s going on,” said Leslie Leland, proprietor and only the third owner of the drug store in well over 100 years.

“I can stand in front of Leslie’s for three hours and meet everyone. Sooner or later you’ll see everybody in town. It’s always been that way,” said Thomas Cox, a third-generation Island resident and proprietor of a hair salon in Boston.

Vineyard Haven is the Island’s year-round port and is widely regarded as the center of the Island business community.

But it is not just businesses — people live there too, in apartments over the stores, many of them overlooking the harbor.

Many are professionals and they love their world.

“Living downtown is very important to me,” said Becca Morrow, a self-employed bookkeeper and classically trained musician. A 12-year veteran of the Vineyard shuffle, she said: “This is the longest I’ve lived in one place on the Island.”

Ms. Morrow has lived for four years on the harbor side of Main street, across the street from the Bunch of Grapes bookstore. She has no plans to move.

“The views are wonderful. My back porch looks out over the harbor and my little balcony in front is right over Main street. It’s great for people-watching. And there is something going on every weekend of the year, snow or shine.

“You know, people tend to look straight ahead or at store windows as they walk. They never look up, so you can really watch without being rude,” she said with a smile.

Reasonable rent is an oxymoron for Island working people. But people who live on Main street in Vineyard Haven say while that the rents may be higher than in Oak Bluffs, they are lower than in Edgartown. And they say the scenic and community benefits of Vineyard Haven living are much greater.

“I moved here more than 30 years ago when my son was nine,” recalled Dick Iacovelli, a local graphic artist. “Within two weeks, he was introducing me to people. He got his first job at nine, sorting Beanie Babies for Beadniks [on Church street off Main street]. I never had to worry about him.”

The faded brick Ben Franklin building on Main street houses several businesses, including a second-floor art gallery, Etherington Fine Art, which provides visitors an opportunity to see the high ceilings, French doors and roomy spaces of late 19th century design.

A key year in the life of Main street Vineyard Haven was 1883, when a fire swept through much of the downtown. Most current buildings date from after that year.

Andrea Hirt, proprietor of Madame Falgoux aromatherapy shop on Main street, and her husband, shared the space briefly in 2006 with Mark Seward, an owner of the Devil’s Dictionary. “It was wonderful, particularly since we relocated here from New Orleans after Hurricane Katrina,” she said, adding:

“I’m a city girl and on the Island, this [Main street] is where the action is.”

Her luck turned even better two years ago when she and her husband won a Tisbury affordable housing lottery. They were able to purchase a home on State Road where they now reside. “If we hadn’t won, I’d still choose to live on Main street,“ she said.

Vineyard Haven bubbles with historians and contrarians and creative and pragmatic people who have a strong sense of their nearly 350-year history, which has included the threat of secession from Massachusetts in the 1970s and defiance of marauding British soldiers 200 years before that on the Island.

Passions can run high in Vineyard Haven. Following a hard-fought electoral battle, a proposal to allow the sale of alcohol in restaurants the historically dry town recently failed by two votes.

As other Island towns have become more seasonal, proprietors of many Vineyard Haven businesses feel a responsibility to their traditional community role: to be open in winter for the Island’s 15,000 year-round residents.

Winter profits are generally nonexistent.

“Being a year-round business is difficult,” said Tim Dobel, owner of Mocha Mott’s in Vineyard Haven and Oak Bluffs. ”People need a place to go and we provide that. We don’t make money in winter but we’ve worked at it and probably now we do enough so we lose less than we would if we were closed.”

There are really two Main streets in Vineyard Haven. At the end of the business district, Main street resolutely marches uphill to West Chop, a residential neighborhood that has embraced the likes of President Woodrow Wilson, and the King of Siam, who was a summer resident in 1926 and 1927.

On the way to West Chop is an area known colloquially as writers’ row, so named for 60 Minutes anchor Mike Wallace and the late William Styron and Art Buchwald, who lived there.

Main street Vineyard Haven has its own brand of sprawl, located a couple of miles up State Road, where a cluster of businesses function as the equivalent of the strip mall found outside most small towns.

Of course, State Road doesn’t look like a strip mall and only local businesses operate there. The Black Dog Cafe on State Road and Woodland Variety & Grill are favorite local haunts.

But back to Main street, with its longtime anchor stores — Brickman’s clothing store, C.B. Stark Jewelers, Bramhall and Dunn and the Bunch of Grapes.

It’s a real-life Main street with an old-fashioned movie theatre — the Capawock — smack in the middle.

The release of the most recent Harry Potter book just happened to coincide with the installation of a large street clock in front of Bunch of Grapes bookstore. The clock looks like it might be at home in the study hall at Hogwarts, Harry’s alma mater.

The tradeoffs between change and tradition are constantly measured. Mr. Cox is not resistant to change, but has a yen for tradition.

“Believe it or not, I still have a resentment that Main street is one-way now,” he said. “As a kid, 30 or more years ago, I loved watching traffic come and go on Main street.”

“It’s vibrant now. The Capawock is back. Main street owners have stepped up,” said Tisbury selectman Jeff Kristal, who is also a past president of the Tisbury Business Association.

“Change is inevitable and ongoing,” he said. “How we guide change is in our control. It can work. Consider this, visitors entering the harbor this year on the new ferry with wi-fi can look up from their laptops as they pass double-masted 18th-century schooners.”