Editor's note: This is the third story in a three-part series that examines the evolution of business in downtown Fairfield and Westport. The first installment focused on commercial changes in recent years. The second installment investigated the economic and political factors in each town that contributed to those changes. This final feature looks at private sector and Town Hall proposals that could transform both communities' downtowns in the future.

Around 1648, five Fairfield settlers moved to an area near what is now Sherwood Island State Park, where they built homes. More transplants from Fairfield joined them, and the settlement of Machamux was established. Almost two hundred years later, that settlement had grown into a town incorporated as Westport.

Some 360 years after that first foray by Fairfielders, their current-day successors still influence their neighbors to the west. As Westport Town Hall officials move forward with a detailed plan to remake their town center, they cite Fairfield as an exemplar for suburban center development.

"In the last couple of years, it seems like I don't have a conversation about our town where people aren't saying, `What's happening to Westport? Why is Fairfield ... so much more attractive?' " says Westport Selectman Shelly Kassen.

The new plan from Westport's Downtown Plan Subcommittee comes after two years of research and consultation with local officials, business owners, residents -- as well as a host of advisers from throughout the Northeast.

A number of ideas -- including expanding pedestrian access along the Saugatuck River, encouraging more downtown business on the west side of the river, reconfiguring parking, and offering more entertainment options in the evening hours -- originate from the town's 2007 Plan of Conservation and Development.

The subcommittee's plan also supports the return of a movie theater to downtown Westport, possibly on Main Street, and generally envisions the transformation of downtown from a retail-focused hub into a mixed-use center.

"We're talking about a whole different way for how Westporters interact with their downtown," says Jonathan Steinberg, the subcommittee's chairman.

Kassen, also a member of the subcommittee, says the components of the plan would probably be considered by town bodies such as the Planning and Zoning Commission, the Representative Town Meeting and the Board of Finance. Public support, she emphasizes, is crucial for implementing any changes.

Many Westport residents appear to support at least the concept of rethinking the look and function of downtown.

Sitting outside Louise's Top This Frozen Yogurt store on Post Road East with her son Nicolai, Birgitte Nissen says she likes how downtown Westport is reminiscent of towns in her native Denmark.

"But I would like to see Main Street pedestrianized," she adds. "And I don't think there's enough use of the water."

"We have such opportunities here given the nature of the downtown," says Don Bergmann, who has lived in Westport for more than 30 years. "If we could have some leadership, some money, some drive, I think some things could be changed."

Any plans for revival, however, face considerable challenges, Town Hall and local business leaders acknowledge. With possible municipal budget cuts looming, Kassen says securing sufficient public money, as well as private funding, for the projects is "a worry."

Parking represents another possible obstacle. The problem has plagued downtown Westport for years, says Drew Friedman, landlord of the Main Street barbecue restaurant, Bobby Q's. He points particularly to the difficulty of balancing various groups' needs.

"That's what we're constantly struggling to find a way around," he says. "How can we find a way to require the employees [who work in the downtown] to park in a remote location, and allow the customer to have unlimited parking downtown?"

The current status of Westport parking stands out as a recurring complaint by many patrons of local businesses.

On a recent Saturday night, Jim and Martha Caron and their two daughters stroll down Main Street after dinner at Bobby Q's. The Carons, who live in New Canaan, say they like the town's ambiance, but would like to see changes in its layout.

"One of the frustrations in coming here to shop is that you often end up driving all over town looking for parking," says Martha Caron.

As possible solutions, the subcommittee's plan suggests building a multi-tiered parking deck at the Baldwin parking lot on Elm Street and introducing metered parking in certain areas.

The issue also figures prominently in the future of Fairfield Center, with many business owners saying they see a need for more parking. To facilitate this, First Selectman Kenneth Flatto supports revising the parking layout along the Post Road. He advocates, in particular, for diagonal parking on one side of Post Road, with an accompanying reduction in street lane width. That idea, however, would require approval at the state level, and Flatto acknowledges that it could "take decades" to be realized.

Flatto says he would also like to explore the idea of using Carter Henry Drive as a market place restricted to pedestrians on weekends. That, however, could not be enacted for at least another year. The town will not assume ownership of Carter Henry's parking spaces adjacent to the Fairfield Railroad Station's eastbound depot until the new Metro Center rail station is completed in late 2011.

Long-term projects could also further expand Fairfield Center, Flatto adds. The most significant development could be at 2190 Post Road at the western edge of downtown. A former industrial tract of more than six acres could eventually be available for commercial redevelopment. But the site's current owner, Exide Group, which once made automobile batteries at a factory there, must first use the site as a staging area for cleaning up lead contamination that seeped from the factory into the nearby Mill River.

Several major Fairfield developers, however, have started to turn their attention to other parts of town. Al Kleban -- whose Kleban Properties firm owns the Fairfield Center Building that replaced the Fairfield Store and the Brick Walk development -- does not foresee his company taking on any new projects in Fairfield Center. Instead, he says the company is focusing on development of properties along Black Rock Turnpike.

Fairfield Center's economic growth has also created new needs, says Patricia Ritchie, the president of the local Chamber of Commerce. She says a new hotel would help the town cope with a continual influx of visitors. The small Inn at Fairfield Beach, for instance, is fully booked for parents' weekends at Fairfield University and Sacred Heart University through 2013. Ritchie also suggests a seafood restaurant be opened near Long Island Sound to complement Fairfield Center's restaurant scene. But such a project is not likely because of limited and expensive seaside real estate, as well as possible opposition from residents.

"It's a great idea, but it would be such a fight," she says.

Regardless of Town Hall plans, noticeable change will likely come to downtown Westport. If and when the Westport Weston Family Y moves to its new Mahackeno location, Bedford Square -- a consortium that includes David Waldman's David Adam Realty -- is scheduled to begin redeveloping the Y's current location at 59 Post Road East in late 2014 or 2015. Waldman says current plans call for the 90,000-square-foot space to become a mixed-used venue with retail, restaurants, and residential units.

Waldman says it would be ideal to start other major development projects downtown during that time frame. "If we're going to have a massive construction project, let's do it once and do it right," he says.

Other downtown business owners also support new development in Westport center.

"We will take any infrastructure changes that come our way to improve business and the overall vitality," says Bob LeRose, the owner of Bobby Q's.

"It's very quiet now at night on Main Street," says Mel Mioli, co-owner of Westport Pizzeria. "I would like to see more restaurants. People need to have a reason to come here after the stores close."

Back in Fairfield Center, Jason Foster-Bey and his wife, Jenny Goodman, enjoy a temperate Saturday afternoon on a bench near the Fairfield Center Building with their 3-month-old son, William, who rests in his mother's arms.

They moved to the town a couple of years ago and rate Fairfield Center's retail and dining amenities highly. But they say things could be even better.

"I would definitely like to see more food stores around here," says Goodman, a freelance graphic designer. "It would be nice to not have to drive out of town to get groceries."

"Yeah, I agree, that would be a good idea," says Foster-Bey, who works for an investment bank in New York.

He smiles at William and then gazes down Post Road, as shoppers pour out of stores in the Fairfield Center Building, which sat vacant a decade ago after the Fairfield Stoer closed.

"And I want to see the town keep bringing in a good mix of chains and independent stores," he adds. "It can't be just about the quantity of stores. Above all, it's got to be about quality."