Most of downtown Vineyard Haven was destroyed by a fire in 1883. William street, however, remained untouched, and it now hosts the longest stretch of old buildings in the town. The tall captain’s houses, built in stately Greek Revival fashion, seem to rest quietly in the leafy shade of the street. The oldest house dates back to 1830.

Inside the stately homes, the street also cultivates a vibrant community.

Howard and Elaine Miller own a house on William street built in 1854 by Leander Daggett, grandson of William Daggett, the street’s namesake. Mr. Miller said the street has a tight-knit community that hosts the best Halloween celebration on the Island. Each year, everyone stocks up on premium candy starting weeks before. On Halloween night the street closes down from 5:30 to 8 p.m., and kids travel from all over the Island to trick or treat.

Many of the old homes once housed whaling captains and their families. — Mark Alan Lovewell

“Last year we had about 1,000 very well behaved kids and parents show up on our doorstep,” Mr. Miller said. “An old fashioned celebration in an old fashioned neighborhood.”

Under the protection of the William street historic district, the residents of the street are subject to regulations about renovations that would alter the outside of their homes. When adding on to the house, Mr. Miller said he and his wife had to adhere to certain parameters, such as keeping old windows.

“We had to make sure we kept the integrity of the old house,” he explained. “We tore down an existing chimney, and restored it brick by brick.”

The street is currently undergoing a renaissance with numerous homes being renovated in recent years.

“Some people perceive the historical district as locations that should be locked in time, but the authors of our bylaw saw the need to allow homes to be expanded and renovated,” said Harold Chapdelaine, chairman of the William street historical district. Smaller seamens’ houses become more desirable when the owners are not locked into a small footprint, he explained.

Close to Main street and the ferry, but a world away. — Mark Alan Lovewell

The house owned by Paul Lazes was built in 1836 as an inn. At the time its owners lived on Main street and housed travelers in the large building. While the lower rooms were for esteemed guests, the small rooms on the top floor were rented to sailors. Later, these small rooms served as a dormitory for school girls from Chilmark.

The inn later sold to a doctor who turned it into a home. His former office is now a downstairs bathroom, and he named the path that leads from the house down to Main street Drummer’s Lane after his beloved horse.

Mr. Lazes began renovating the house in 2013, customizing the interior layout and accents.

“I am accustomed to working with traditional buildings and contemporary lifestyles,” he said.

The street is known Island-wide as a beacon for trick-or-treaters. — Mark Alan Lovewell

Mr. Lazes’s wife, Jaime Hamlin, noted that from the upstairs porch they can hear the steamship whistle blow. “It just reminds you that you are on the Island,” she said.

Last winter, hunkering down on the street during the deep snowfalls became a community event. “In the snowstorm my husband Paul maniacally cooked all day, and everyone trudged through the snow to come have dinner,” Ms. Hamlin said.

Wiet and John Bacheller have lived on William street since 1976 in one of the newer homes built in 1908. When they moved in with their three-year-old twins, they were the youngest couple on the block.

“Neighbors would joke we lowered the average age to 60,” said Mrs. Bacheller. Now, she said, there are no young children who live on the street year round. Before they lived on William street, the Bachellers would go out for the night on Halloween.

“Now we don’t dare to not be home,” Mrs. Bacheller said. “It’s Halloween, we can’t go!”

Their house became something of a dorm room when their children’s up-Island friends needed to catch an early ferry for field trips. The Bacheller children have children of their own now.

“Our grandchildren think they own Owen Park,” Mrs. Bacheller said with a laugh.

Through the years, Mrs. Bacheller has seen the neighborhood change. Lately, there has been a lot of renovation and construction on the street, though less homes are used year round, she said.

“A lot of people are not really living there, it’s their second house, something like that,” she said.

Alisan Lohan-Conway lives on William street and sells on William street. As a real estate broker she is well versed in the homes on the market.

“The mix of people is eclectic, from intellectuals to business people to artistic people,” she said.

Ms. Lohan-Conway said the street has charm and character which gives it a real sense of belonging. And when she steps out her door, the street orients her.

“I know where I am,” she said. “I am on Martha’s Vineyard.”