A decade ago, Chestertown seemed destined to lose its connection to its namesake river. But with a second chance from the Great Recession, one of the Chesapeake region’s most picturesque waterfront towns is now on course to becoming one of its most water-accessible.

Chestertown has bought the town’s sole surviving marina, which was slated for condos and private-only access to the Chester River. The municipality plans to raise the wharf by 2 feet, dredge the harbor, rebuild the piers and refurbish the boat slips. The facility will then connect to the rest of the town through a half-mile promenade that Washington College now owns, which will also lead to a new campus being built for the school’s environmental programs.

When completed, the town’s nearly $5 million investment will be the only public access point to the Chester for 10 miles in either direction, helping to fulfill a Chesapeake Bay Watershed Agreement objective to increase public access to an increasingly privatized waterfront. It will not only draw pleasure boaters who might otherwise head to marina-rich towns like Oxford and St. Michaels, but also kayakers, paddle boarders and other recreational users who now struggle to find a way ashore.

“This is the last access point, not just for people who live here, but for people who want to come here by boat,” said Chestertown Mayor Chris Cerino. “It has the potential to be a tremendous asset to town.”

Buying a marina is a risky bet for any town, but maybe more so in Chestertown, where at least half the property is off the tax rolls because it’s owned by the nonprofit college and the hospital, a branch of the University of Maryland Medical System. But experts say towns must take such risks to maintain their identities, spur economic development and build connections between residents and the natural environment.

“There’s literally almost no city that isn’t trying to do this. The challenge for small towns is how do you pay for it?” said Ed McMahon, senior resident fellow at the Urban Land Institute, a development think tank in Washington.

McMahon has visited Chestertown many times for lectures and has been on friendly terms with various city officials. Like many visitors, he thinks Chestertown has many advantages: pretty, well-preserved homes; good restaurants; quaint shops. But many Chesapeake towns boast the same advantages, among them Annapolis, Cambridge, Easton and Berlin.

“One of the things we learned — if you can’t differentiate your community from any other, you simply will have no competitive advantage,” McMahon added.

Regionally, other towns are attempting to secure public access for the same reasons as Chestertown. Havre De Grace has already done so, with a town promenade that connects its duck decoy heritage with local restaurants and stunning views. Easton is planning for public access to the water along its Fourth Street corridor. Cambridge has a plan to develop its own marine terminal.

All of those are what Katie Parks of the Eastern Shore Land Conservancy’s Center for Towns calls “vibrancy markers” — touchstones that let a community stand out. Public access, she said, is one of the most important.

“When the waterfront is in private ownership, it’s definitely a loss to the community,” Parks said.

Nationwide, McMahon said, Chesapeake towns can look to places like Charleston, SC, where the most valuable land is in the parks that abut the waterfront. Cities like Hartford, CT, are trying to get closer to their waterfront after building freeways along it decades ago.

Chestertown’s marina purchase, however popular now with planners, was anything but a sure thing a decade ago. Then, the town was mulling three annexation proposals that would have allowed the construction of more than 2,000 homes, doubling the population. Most Shore towns were in the same boat, looking to residential growth to bolster flagging tax bases as real estate agents touted “the commutable Shore” to prospective buyers who worked in Annapolis, DC and Baltimore.

By 2007, 310-year-old Chestertown, which the English had designated the state’s second leading port, after Annapolis, had lost one of its two marinas to condos. An influential developer, Roy Kirby Jr., had bought the other. Kirby wanted to build piers 350 feet into the river.

He had also bought Stepne Manor, a 70-acre farm not far from the marina, where he planned to build houses. “There were a lot of big changes being discussed that would have altered the character of the town,” said Serino, who was a member of the planning commission then. Kirby’s marina plans, Serino remembers, were “so out of scale with the town.”

The annexations failed, stymied by slumping housing sales and a resistant planning commission. Washington College bought the town’s Armory, a large property that the military was unloading, and acquired the land around it, which became the basis for the river walk and satellite campus. The college also acquired a strip of waterfront that connected the once-private marina to Stepne Manor and a public park, all within a short walk of the historic district.

Kirby put the marina on the market in 2012. The college, which had partnered with the developer in buying Stepne Manor, bought out his interest in it.

Four years ago, then-Mayor Margo Bailey led the town to buy the marina. When Serino succeeded her in 2014, he said there was still no formal plan for what to do with the facility.

As vice president for the Sultana Education Foundation, Cerino knew a marina could be costly to maintain. This one came with about $3 million in deferred maintenance, including dredging — and that was on top of the $2 million just to buy it. Planners said the wharf needed to be raised about 2 feet to reduce flooding at the marina, an adjacent restaurant and local docks that host ships for educational purposes.

So far, Chestertown has secured more than $1 million in grants to improve the marina, and has a dredging permit from the Department of Natural Resources to begin preparing the river for boats. The town negotiated with the owners of a neighboring restaurant, the Fish Whistle, to raise their parking lot property and prevent the flooding, which has been a semi-regular occurrence since Tropical Storm Isabel destroyed the property in 2003.

Local officials are looking for help from the U.S. Department of Agriculture to finish the marina project. With the town’s small tax base, it’s a challenge coming up with funds to match federal grants, so Cerino said the town may have to try some private fund-raising.

Last year, Chestertown earned its designation from the state as an arts and entertainment district. The college launched a program, called SANDBOX, to foster a connection between art and science and the natural environment. The effort got three years of funding from the Andrew W. Mellon Foundation, and noted Baltimore architect Alex Castro signed on to direct the program.

Castro came of age as an architect in a city filled with public art and a quirky sensibility. He designed part of the American Visionary Arts Museum, as well as the conversion of a historic cable car barn into a movie house as the Charles Theatre. He also created a new icon for the city’s skyline, the Natty Boh neon sign atop an 11-story tower in a revitalized Brewer’s Hill neighborhood.

“Art can be an economic driver within a town,” said Castro, now a resident of the Shore town. “For Chestertown, it’s really critical to have that waterfront access. Art is a big draw, and that is becoming more evident. This is part of the master plan for public art here.”

If Chestertown can secure the money to finish the project, it will have it all: a waterfront protected from nuisance flooding that also offers public access to the water that’s been integral to the history of the community.

Well, almost all. The town could still use a mid-size hotel in its historic district, he suggested, to house all of the new paddlers and art lovers who are just discovering it.

“We keep hoping,” Castro said.

(Chestertown Mayor Chris Cerino's name was misspelled earlier. The Bay Journal regrets the error.)