It’s not unusual to see a group of people traveling the streets of Oak Bluffs together, to see them stop in the middle of a Circuit avenue sidewalk and gaze up at a historic building, or stand next to the Tabernacle and take in the quiet calm of the Camp Ground.

But the group touring the resort community Monday morning were not tourists.

As business owners and town officials, these men and women walk these streets every day. But on Monday, accompanied by the state department of Housing and Community Development, they adopted the critical lens of an outsider and surveyed their town for areas of improvement.

Town administrator Bob Whritenour had recruited the state officials to ferry to the Island for the day. Their guides showed them around and, in turn, the grant agency shared ideas about how to improve the town.

“We are trying to rebound from a very long, difficult economic period . . . our community has taken a huge hit over the past few years,” Mr. Whritenour told the state representatives at the beginning of the tour, standing in front of the Civil War statue. “What we are trying to examine are ways that we can as a government agency stimulate that private investment that is needed.”

The sales pitch involved singling out many parts of town that have been recently renovated, as well as pointing to areas in need of investment. Throughout the two-hour walking tour that snaked through the downtown streets, government officials and business owners painted the needs of the town with broad strokes, naming the recession and hurricane damage as challenges to be overcome. They discussed Circuit avenue at length, traversing the entire length of the street.

“The one that’s a real tough nut, and you’ll see it as we walk through, is the whole issue of how do we assist the local business owners and the property owners . . . in getting investment going that is necessary to affect downtown,” Mr. Whritenour said. “There have been some private investment in some of our historic buildings, but what we are trying to do is create more of a momentum.”

Town leaders also pointed to specific areas in need of attention, including a number of vacant storefronts and streets lacking sidewalks.

They discussed the status of the two movie houses which remained shuttered all summer. Both the Strand and the Island theatres, owned by the Hall family, are historic buildings that have suffered deterioration in recent years.

“As you can see, to have a blighting influence right at the front door of Circuit avenue is significant for us,” Mr. Whritenour said. “But it’s just one of a series of issues we are hoping to [get] a strategy for.”

Oak Bluffs Business Association executive director Christine Todd said the impact of the vacant theatres goes beyond aesthetic concerns. She said the cinemas are essential to attracting families to the town during the evenings. “That entire population is not coming to Oak Bluffs because we don’t have a theatre here,” she said.

Mr. Whritenour proposed that the town apply for public funding to renovate the Island movie house, and encourage a nonprofit group to operate the theatre.

“There are models for it, but the building owner has to be willing,” said Emmy Hahn, a specialist in the area of downtown revitalization who has helped revitalize other communities throughout the state.

Later, during a lunch meeting at the Lookout Tavern on Sea View Extension (the tavern is owned by selectman Michael Santoro), participants continued to express frustration with the Hall family.

But Ms. Hahn advised them not to focus their energy on one property owner. Instead, she suggested the town approach those willing to invest in their buildings, and get some momentum going throughout the town. “Don’t get bogged down in pieces that you can’t do,” she said. “Let’s move forward, otherwise you get consumed.”

John Tiernan, co-owner of the Dockside Inn, said he believes the best-looking buildings on Circuit avenue are owner-occupied. Those who lease their storefronts to other businesspeople have less incentive to maintain their buildings, he said.

As the group stopped at Post Office Square, discussion turned to the issue of midsummer parking. “Parking is at a premium,” said Oak Bluffs Association treasurer Keith Enos.

But Primo Lombardi, owner of the Martha’s Vineyard Yoga Center and longtime Circuit avenue business owner, stressed a need to widen sidewalks on the avenue instead. Often, he said, visitors have to step into the street in order to avoid brushing up against each other on narrow sidewalks. “We have more people walking in town than driving,” he said. “We want to promote that.”

Throughout, seasoned community members imagined that they were daytrippers, seeing the town for the first time.

They wondered where tourists tended to walk in the downtown area, and how clearly marked their prospective destinations were. Lingering by the public restrooms off Kennebec, Mr. Whritenour briefed state officials on the ongoing debate between the town and a Circuit avenue property owner who wants to lease his space to food trucks and retail pushcarts.“It is a fascinating discussion,” Mr. Whritenour said. “It has made for some of the most heated debates.”

Following a brief visit to the docks around the Island Queen, talk turned again to day trippers, with discussion about possible improvements to signs, and circulation of informational brochures and maps.

In the end, the state officials were hesitant to give specific grant recommendations at this early stage in the process, but Ms. Hahn did offer some general guidance.

She said she’d heard a number of different priorities voiced throughout the day and recommended that the community convene a meeting to poll a broad cross-section of interested parties. “I think you need some consensus,” she said.

Overall, her analysis of the town was positive. She praised the strong showing of community members at the site visit. “The most positive thing you have here is the level of interest, the people talking,” Ms. Hahn said. Her colleague, Patricia Roushanaei, said she’d never seen such a reception at a site visit before.

“The level of enthusiasm from business owners is really incredible,” Mr. Whritenour said.

But Ms. Hahn said there is still work to be done. “You have a viable downtown, but there are pieces that are missing,” she said.

She suggested the town create a map of areas needing improvements. In order to receive funds earmarked for commercial rehabilitation, a community must document that a substantial area of the business district is affected by blight. Then the town can apply for grants to help pay for new signs and the renovation of building facades, or perform a study of possible areas for increased parking.

Ms. Hahn also suggested a survey of the building owners to find out why they are not investing in their properties. “Ask them, what kind of program would get you to invest?”