Westport Weston Family Y officials recently embarked on a field trip. They traveled 2 miles north from their downtown headquarters to the Y's 32-acre Mahackeno campus in northwest Westport.

Once there, they donned hard hats and took a short walk. They passed towering mounds of fill, while bulldozers and diggers roamed around and sorted through the earthen deposits. After a few hundred yards, they stopped at an embankment to survey the excavation. Looking toward the other side of the hollow, they pointed at a concrete wall rising from the terrain. Nearer to them, they spotted a maze of reinforcing steel. From these structural seedlings, a 54,000-square-foot complex will sprout during the next 18 months -- the Y's new home, a project years in the making.

"When we get people out on a tour, they have no idea of the scope and breadth of what this facility really is," said Paul Bernetsky, the Y's chief development officer, as he gazed at the structure taking shape. "There's a wow factor when they walk up to this."

A year ago, Mahackeno looked largely like it did in 1938 when the Y's summer day camp opened. The property's transformation during the last year is evidence of an important milestone: The Y raised enough money to begin construction in February of the $38.5 million complex. Most of that cost will be funded by the sale of the Y's downtown building, debt financing and an investment fund. But the Y's target of $15 million in contributions is a crucial piece in that capital puzzle.

The Y's fundraising drive accounts for only one of several major capital campaigns underway or planned in Westport.

Within a half-mile radius of the Y's downtown home, the Levitt Pavilion for the Performing Arts, the Westport Public Library, the Westport Cinema Initiative, the Westport Arts Center and Saugatuck Congregational Church are all planning major capital projects. The overlapping initiatives point to the rising prominence of the town center and what could emerge as one of the most intense periods of fundraising in the town's history.

Whether all of these organizations reach their fundraising goals and move ahead with their plans is not certain. But if realized, their projects could have a transformative effect, not just for their own constituencies, but the entire town.

Years in the making

Most of those capital campaigns are driven by long-standing organizational and community needs and goals.

For more than a decade, Y officials have wanted to relocate their headquarters from 59 Post Road East to provide improved and expanded services to the Y's approximately 5,000 members. Y leaders often refer to the downtown building's lack of "usable" space, a limitation imposed by the idiosyncratic layout of the vintage structure.

Before the Y launched its Building What Matters capital campaign for its new home, the project faced a protracted and acrimonious review by town boards such as the Planning and Zoning Commission. After securing town officials' approval, Y officials then grappled with a series of lawsuits against the Mahackeno plan. Finally, after the last of those challenges was dismissed in January 2011, the Y launched the capital drive -- nine years after its Board of Directors approved Mahackeno as the site for its new headquarters.

Y officials acknowledge the controversy surrounding the project has hindered fundraising. But they have maintained that the project warrants community investment.

"This is just a dream come true for a lot of people," said Rob Reeves, the Y's chief executive officer. "We'll have a facility that can serve all ages."

Like the Y, the Westport Public Library constitutes one of the town's largest service-providers. More than 1,300 people visit every day, or about 5 percent of Westport's total population.

To more effectively serve patrons, library officials are developing a "transformation" plan, which would expand its building at 20 Jesup Road from 48,000 square feet to 65,000 square feet, while minimally increasing the structure's footprint. They are targeting a 2015 groundbreaking for the project, which would take about two years to complete, according to Maxine Bleiweis, the library's director.

The initiative has an estimated $25 million price tag, $5 million of which could be funded by the town, according to the town's latest five-year capital forecast.

"Within the transformation, every single area of the library will be enhanced and improved from a functional and flexibility perspective," Bleiweis said. "In the morning, a space could be used for one purpose and then another in the afternoon. It'll be so much more conducive to learning and thinking and bringing out all the great ideas that people have in Westport, for all ages at all stages of their lives."

Westport Arts Center officials say space constraints are also increasingly affecting their organization's services, which reach about 7,000 people each year. They are exploring relocating their headquarters from its 3,600-square-foot building at 51 Riverside Ave. to a new home on Jesup Green next to the library. The new venue could encompass about 7,000 square feet, according to Peter Van Heerden, the arts center's executive director.

"We're reaching a zenith because we don't have a big enough space to do things," Van Heerden said. "You get to a critical mass, and then you have to start to think about what's next."

Across the Saugatuck River from the Westport Arts Center, a new era at the Levitt Pavilion is set to premiere later this month: construction of a $6.7 million complex to host the pavilion's annual summer series of outdoor concerts. A staple of the town's performing-arts scene since 1974, the Levitt's popularity and long-term exposure to the elements necessitated a contemporary replacement for its old bandshell, said Freda Welsh, the pavilion's executive director.

"It really came to a head in 2007 because at that point we had put on so many band-aids on the existing pavilion that it could no longer do the job," she said. "So we decided the best thing we could do was to pursue this great new opportunity."

The nonprofit Westport Cinema Initiative, meanwhile, is responding to a long-time -- and surprising -- void in a town renowned for its arts community. Since 1999, when the downtown Fine Arts theaters closed, Westport has lacked a movie house. That absence is frequently referenced by town officials, downtown merchants and other community leaders when they discuss efforts to boost evening activity in the town center.

WCI leaders envision a three-screen "arthouse" cinema in a lot adjacent to the Main Street restaurant Tavern on Main. The theater would have a nonprofit membership model as well, as an educational focus.

"The goal is to bring to Westport films for all ages," said Sandy Lefkowitz, WCI's director. "We see ourselves as an example of what Westport at its best can produce. It's about the communal experience."

In contrast to the other projects, sudden and unwanted circumstances catalyzed Saugatuck Congregational Church's fundraising drive. A massive fire Nov. 20, 2011, destroyed most of the rear portion of the church complex at 245 Post Road East, which housed offices, nursery-school classrooms and meeting rooms.

In December 2012, the Planning and Zoning Commission approved a site plan proposed by church officials to address the damage. The restoration will include refurbishment of the rooms destroyed by the fire and a reconfigured third floor featuring a youth room, choir room and small chapel. In addition, a new terrace will be built between the church's garden and Hoskins Hall, a social room beneath the church's sanctuary.

The renovations will not change the church's landmark sanctuary and steeple.

"I'm very optimistic," said John Walsh, chairman of the church's building committee. "There's a real excitement in the congregation right now because they finally see this coming together."

Church officials are targeting a mid-summer start to the restoration and a return to their building in the fall of 2014.

Raising the money

Fundraising for a major capital project entails a long, complex and often-frustrating process. The Building What Matters campaign illustrates the challenges. When Y officials launched the initiative in early 2011, they originally hoped to build a 102,000-square-foot center in a single undertaking. A year later, they languished more than $16 million short of their fundraising goal. As a result, the Y's Boards of Directors and Trustees voted in February 2012 to build 54,000 square feet in a first phase, with an option to later expand to 102,000 square feet.

During the following three months, Y officials ramped up their public outreach, warning that if fundraising did not pick up they would have to consider abandoning the Mahackeno project. In May 2012, buoyed by several major contributions during the preceding two months, they decided to proceed with construction.

The Y's capital-campaign haul now totals about $12 million. It needs to raise another $2.9 million, a goal it plans to reach by the Mahackeno center's opening in the fall of 2014, according to Bernetsky.

"There's a renewed spirit among our board and volunteers to get this done," he said. "They've worked very hard, but now they see the light at the end of the tunnel. A building is coming out of the ground, and I think that will encourage people to participate in this campaign."

Levitt Pavilion officials have also grappled with unexpected fundraising difficulties. Last year, they targeted a September 2012 groundbreaking, anticipating they would reach by then their approximately $4.75 million private-funding goal needed to start construction. But another seven months would elapse before they hit that target.

"We started the [capital] campaign in 2009, and I think we may have anticipated it may have been over in 2011, but this was our first capital campaign, and we were probably overly optimistic," Welsh said. "I think the reality is that most capital campaigns take quite a bit longer than that."

She declined to specify the reasons for the delay, but maintained that her organization is well-positioned for the long-term. Assuming the groundbreaking goes ahead this month, the new Levitt Pavilion would open for the 2014 season.

Despite the imminent groundbreaking, fundraising will continue. Pavilion officials are now looking to recoup "soft" project costs such as consultants' fees and soil studies, boost the pavilion's endowment and build up capital to cover increased operational costs for the new complex.

Westport Cinema Initiative launched its capital campaign at its founding in 2011. It is working toward a $4 million goal -- $3 million for the theater and $1 million to cover two years of operating expenses. WCI officials have not disclosed how much the campaign has raised so far.

In the meantime, the group has established a prominent fundraising presence and covered operating costs through contributions from "angel" supporters, charter memberships, sponsorships and a popular series of screenings at venues such as Town Hall, Toquet Hall and the Westport Country Playhouse.

Saugatuck Congregational Church started its capital campaign in March and has so far raised approximately $1.1 million of its $2.6 million target.

"This is a campaign addressed to our church congregants and friends," said John Canning, the campaign's chairman. "I firmly believe that we first need to show what the church members are ready to do on this."

Fundraising for a new Westport Arts Center is in a nascent stage. The nonprofit has garnered commitments totaling several million dollars, but has not yet started a public campaign, according to Van Heerden. He estimates the new venue, if approved, could cost between $5 and $7 million.

In the meantime, mindful of the need for broad public backing, an arts center building committee has reached out to town officials and downtown business owners to seek their input.

The library's capital campaign is in a quiet phase. It has not released fundraising tallies yet.

Despite their concurrent campaigns, leaders of the local nonprofits insist they are not competing for donors.

"Our missions are different," Lefkowitz said. "I don't want somebody to take money away from one to give it to us. We're privileged to have such fine institutions, and they should be the best they can be."

Other Westport nonprofit executives also express confidence that the town can simultaneously support several major capital campaigns.

"It's a hugely generous community," said Jeff Wieser, president and chief executive officer of Homes with Hope, which provides emergency shelter and supportive housing. "I'm amazed at all the different organizations they support and the care the community provides to all the citizens of Westport."

Looking ahead

The emergence of these projects may foretell a period of major, lasting change in Westport, particularly in the town center. The Y's move will pave the way for the redevelopment of 59 Post Road East into a mixed-use complex -- a multi-use project that promises to change the face of downtown.

The scale and pace of change elsewhere in the town center will depend heavily on fundraising progress and, for some projects, other factors such as approvals from town boards.

Construction of the Levitt Pavilion complex and restoration of Saugatuck Congregational Church will likely occur first. Within the next five years, the library's transformation, the relocation of the arts center and building a WCI movie house could follow.

The prospective confluence of projects highlights the need for town involvement in their planning, argues Lou Gagliano, chairman of the town's Downtown 2020 Committee.

"When you think of all of those moving parts and when you think of all the unmet community needs, the only way you're going to bring all these together is to do a master plan," he said.

For some organizations, parallel fundraising and building schedules present opportunities for new partnerships. Westport Public Library and Westport Arts Center officials have said that the arts center's proposed relocation to Jesup Green, along with the library's transformation, could create a cultural center reminiscent of a liberal arts college.

"Our transformed facility will enhance any institution close by because of the kind of traffic that we get," Bleiweis said. "It's an intellectually curious population. Being a driver to other places is important. You have to have those anchors in the community."

Van Heerden shared a similar vision of the future relationship between the library and arts center. If the updated library features an auditorium, he said such a venue would be ideal, for instance, for chamber-music concerts hosted by the arts center.

"A building is second nature," he added. "For me, a cultural campus is about educating and providing the public with a resource they may not otherwise have. It's part of our mission. It's to make sure we foster the building of the community."