Manhattan is a tight little island. Around thirteen miles long, it has a width that varies from two miles to a few hundred feet. After centuries of having its shores sculpted by erosion, excavation and landfill, it is a land mass that has acquired on maps the profile of a right whale swimming into the open sea. But this nautical image is too neat, if not another of the city’s cruel jokes, since Manhattan is a small island that can often make one feel utterly landlocked. The financial district is formed by granite and glass canyons; in midtown, trade and tourism funnel crowds inland toward Central Park, Times Square and Madison and Park avenues. A tenement roof offers some respite–a vista of sky vaulting a sea of shingle, tin, terra cotta and tar. The soft wails of unseen tugs linger in the air, and the nearest body of water lies in the many cubic yards of upstate reservoir stored in the squat elevated towers cluttering the horizon. From the roof the cables of the Brooklyn and Manhattan bridges are visible, but the river they span is not. At night, glittering with tiny lights, the cables dip from their towers into the dark, the extravagant decorations of a street fair for the landlocked.

A glimpse from an airplane or a skyscraper’s upper stories reveals a different picture. Wedged between three rivers, Manhattan is part of a large urban archipelago. Of New York City’s five boroughs, only the Bronx rests on the continent. Staten Island looms in the southwest, and to the east Brooklyn and Queens blanket the western tip of Long Island. A host of smaller islands dot the harbor and rivers. Liberty Island houses a monument, Rikers a prison. Lesser-known islands like North Brother, once used as quarantines for the criminal and the ill, are now inhabited by birds, insects and mice. Freshwater tributaries feed the rivers that ribbon the islands, which means that the Manhattan archipelago is bathed by an estuary, a nutrient-rich marine habitat created by the merging of fresh and salt water.

Phillip Lopate explains in Waterfront that when he began telling people he was writing about Manhattan’s shoreline, “many would get misty-eyed and ask me if I had read The Bottom of the Harbor (which of course I had).” It’s a legitimate question since few books convey a richer sense of the fecundity of Manhattan’s estuary than Joseph Mitchell’s work, which contains six delicate and dazzling portraits of the waterfront that Mitchell published in The New Yorker between 1944 and 1959. The Bottom of the Harbor is an estuarium, one that elegantly combines, as Lopate acknowledges, “the perspectives of marine biologist, geologist, urbanist, anthropologist, and historian” to explain how the harbor churns together past and present, nature and humanity, predators and prey.

But to get sentimental and imply that Mitchell had already done the job in The Bottom of the Harbor is to diminish the importance of Lopate’s very different but perceptive and valuable Waterfront. Even if he had wanted to, Lopate couldn’t have written a book like The Bottom of the Harbor, since Mitchell’s subject, the culture of New York City’s maritime economy, has all but vanished. By the early twentieth century most of the immense oyster beds in the Lower Bay, decimated by overharvesting and pollution, had been condemned. As for fin fish, they “stopped arriving by water in the early 1970s,” Lopate tells us, “partly because New York Harbor was too polluted to supply a local catch (or store it in the river, once caught),” and partly because it was cheaper to truck in refrigerated fish from elsewhere. The biggest economic blow came in the 1960s, with the arrival of container ships, which require deep drafts and fifty acres of backspace for the unloading of cargo, both of which Manhattan lacks. After World War II, the city handled one-third of all foreign cargo shipped to the United States; by the early 1970s, after the maritime trade had drifted westward to the deep waters and acreage of container facilities in Newark, Manhattan’s port was all but dead. (The piers in Red Hook, Brooklyn, have remained the home of a few small, vibrant shipping firms.) What was once a shoreline thick with bustling piers, wharves and ferry slips is now a hodgepodge of parks, piers, promenades, luxury apartment buildings, landmarks, housing projects, power plants and parking lots. No wonder, then, that when Lopate examines Manhattan’s profile on a map, instead of a right whale he sees “a luxury liner, permanently docked, going nowhere.”

Lopate takes us nearly everywhere as he meanders up and down the banks of the Hudson, Harlem and East rivers, from the Battery in the south to Inwood Park in the far north, and from South Street Seaport to Highbridge Park in East Harlem. Strolling along promenades, scrambling over train tracks, slogging through underbrush, squeezing through holes in chain-link fences, Lopate hugs the water’s edge as much as possible. Interspersed among the chapters describing these rambles are excursions into the history of the waterfront’s architecture, geology, literature and development. Underlying these explorations are several fundamental questions: “What is our capacity for city-making at this historical juncture? How did we formerly build cities with such casual conviction, and can we still come up with bold, integrated visions and ambitious works? What is the changing meaning of public space? How to resolve the antiurban bias in our national character with the need to sustain a vital city environment?”

Waterfront is a vivid blend of history, guidebook, white paper and urban sketch, one that may surprise readers of Lopate’s work as a personal essayist. Yet the waterfront is a natural subject for Lopate, since local history has often been a catalyst for his essays. “I am like a worm that prefers to enter a dying organism,” Lopate writes in “Memories of Greenwich Village,” from his collection Portrait of My Body. “It excites my imagination more to take an archival angle on the past than to go where it is ‘happening.'” In several essays in the early collection Bachelorhood, that angle of vision is sharp but narrow: Lopate describes how seedy, vibrant neighborhoods (such as Times Square and the Upper West Side) began to be transformed or threatened by gentrification in the late 1970s, and his observations, while vivid, are mostly impressionistic.

Lopate refined his archival vision in a novel, The Rug Merchant, in which the owner of a sleepy Oriental rug shop on Amsterdam Avenue has his rent tripled by gentrification-happy landlords. The unfashionable shop is a dying organism, one that its owner has for personal reasons maintained in a makeshift way; Cyrus Irani inherited the shop from an uncle, and he had started working there only after the fear of success led him to abandon his doctoral studies in art history. Although Cyrus’s store is on Amsterdam Avenue, the distance between it and the shoreline described in Waterfront is narrow, since in his new book Lopate is again burrowing into the remains of a local enterprise that for centuries had a makeshift feel. As Lopate notes, the relatively calm waters of New York City’s sheltered harbor saved it the expense of building stone piers, and when ships began getting wider and longer, the city opted simply to lengthen its rickety wooden piers instead of replacing them with sturdier, more expensive ones. In The Rug Merchant Lopate tells the subtle story of a place’s inertia and slow decline; in Waterfront he tells a rich and more subtle story about a place’s rapid decline followed by equal parts of inertia and transformation.

Inertia: Battery Park City, a cluster of residential, commercial and recreational developments built on ninety-two acres of landfill, part of which was extracted from the excavation of the World Trade Center site in the late 1960s. Because its design severs it from its immediate context (the Wall Street financial district), Battery Park City is, in Lopate’s opinion, “something of a transplanted organ that has never quite taken hold.” Transformation: the Riverbank State Park, nestled atop a sewage treatment plant on the Hudson between West 137th and West 145th Streets. Harlem residents were understandably outraged when they learned in the late 1970s that the state wanted to build along their neighborhood’s western edge a plant for processing the effluents of millions of people. The state’s consolation prize was to erect a park atop the plant. Nearly 4 million visitors a year now flock to Riverbank’s ballfields, pools, amphitheater and cultural center, Lopate says. (An added attraction: the state finally figured out how to eliminate the plant’s stench.) Lopate praises Riverbank’s designer, Richard Dattner, for refusing to treat its waterfront location as either the outer edge of residential development patterns or an empty vista for soothing the landlocked. Like Lopate, Dattner resists the island’s deeply ingrained habit of turning inland.

During his many decades as an essayist, Lopate has cultivated a prose style that’s supple and vigorous enough to tackle diverse tasks, such as tender reminiscence (“The Dead Father: A Remembrance of Donald Barthelme”), sardonic self-revelation (“On Leaving Bachelorhood”) or contrarian argument (“Resistance to the Holocaust,” an eloquent, sharp-elbowed attack on writers, museums and memorials whose representations of the Holocaust are mired in mystification and kitsch). Writing directly about the waterfront, Lopate had to inventory facts and impressions about scores of physical places. It’s a task with no precedent in his other work, and one that he handles deftly by punctuating his lively historical and geographical excursions with colorful bursts of description. The Starrett-Lehigh Building, a blocklong, nineteen-story warehouse near the Hudson River, is a “flapjack stack of fenestration.” Ten blocks north sits the Jacob K. Javits Convention Center; with nearly 2 million square feet of space warehoused under a canopy of black glass, it is a “bold lump of coal.” The Con Edison power plant on the banks of the East River at 14th Street sprouts “stacks of coiled wire like the laboratory headdress of Elsa Lanchester in The Bride of Frankenstein.” As for the joggers, cyclists and rollerbladers who dart and glide through Hudson River Park, they are clad in “the global uniforms of the body-snatched, those who have allowed their limbs to be turned over to machines for happiness.”

Such growls about the waterfront’s temples of finance and sweat should not be mistaken for bohemian sneers. Lopate admits that he recoils from places like Hudson River Park and Chelsea Piers not out of principled urbanist objections to their design but because of “my own estrangement from my body, and my fear and envy of people who celebrate life through their pores–I who live in my head, looking out at the world as if I were constantly reading a book, while my belly softens and my hair thins.” Still, a balding pate can’t account for the passages in Waterfront that echo Low Life, Luc Sante’s hip and pungent history of downtown Manhattan’s nineteenth-century underbelly. While tracing the boundaries of the old fish market in South Street Seaport, Lopate reminisces about long-gone purveyors of vice who lived by their wits “with improvised cons at the border of legality. In the end, that way of life could not survive here: it fell to the corporations and realtors who call the tune in this city, and who practiced a smoother type of dishonesty, breaking their promise to the fish-dealers.” In Low Life, Sante presents those nineteenth-century hustlers as the guardian spirits of an urban wilderness, an unfinished Wonder City poisoned in the early twentieth century, and again during the 1980s and ’90s, by prosperity and public relations. Sante treats those scruffy spirits as the source of a regenerative myth; they are the protagonists of a morality play about the struggle between flamboyance and sobriety, the irrational and the rational. There is no such struggle in Waterfront because, despite being a flâneur, Lopate is not a bohemian who romanticizes poverty or marginal classes. He is curious about the waterfront’s past shabbiness but not inured to it.

As for principled urbanist opinions about waterfront development, Lopate has a bushel of them. One is a revisionist take on Robert Moses, the master builder of many of New York City’s tunnels, expressways, parks, beaches and bridges. Lopate defends Moses against those who, like Jane Jacobs and Marshall Berman, think he was “a monster, the enemy of the good” because he bulldozed through waterfront neighborhoods to build highways. I credit Lopate for his effort, but I think it will take more than a few thousand words, and better arguments than the claim that Moses “accomplished much more good than harm” or that some of the neighborhoods he razed to make way for an expressway “were doomed to change and wither” anyway, to convince thoughtful skeptics that Moses was not an imperious planner indifferent to the plight of the thousands of lower-class folks displaced by his projects.

Much more persuasive is Lopate’s carefully researched and gamely argued discussion of Westway–“the road not taken.” Announced in 1972, Westway involved a plan to submerge several miles of the West Side Highway in the Hudson River, thereby creating the opportunity to build an expansive waterfront park downtown. Better yet, because Westway was to be part of the nation’s Interstate system, the federal government would pay for its riverine tunnels. Westway had many opponents in Greenwich Village, which would have been most affected by its construction. After failing to prove that Westway would worsen their neighborhood’s air quality, village activists argued that its tunnels would harm marine life, especially striped bass. The state countered that it was willing to do whatever was necessary to ease any impact Westway might have on the fish. Striped bass have adapted to landfill and dredging in the past, Westway’s planners argued. Why not now? The courts agreed with the opposition, and Westway was scrapped in 1990.

The Westway chapter shows that, as far as urban planning goes, Lopate is a conservationist. As the architect Nathan Silver explains in Lost New York, preservation, through the limited protection and veneration of certain urban forms, keeps change at bay, whereas conservation seeks to accommodate change by cultivating ways of sustaining a certain type of urban milieu, such as an informal, pedestrian culture. Conservation can involve preservation, but preservation can’t include conservation. “The battle of Westway was a triumph of People Power over the Establishment,” Lopate rightly concludes. “This time, however, the Establishment had the progressive vision and imagination, and the people…dug in their heels.” It was a triumph of preservationists over conservationists, of advocates for striped bass over advocates for striped bass and a sprawling park. Westway’s legacy, Lopate surmises, is that New York City “is ruled by a fractious civic culture, better suited to stop anything from getting built, than to respond creatively and energetically to the need for fresh urban solutions.”

Lopate concludes his book with a survey of such solutions, and even those who quibble about the details or nod off at the slightest whiff of white-paper wonkery will be hard-pressed not to appreciate the most valuable feature of Waterfront, Lopate’s quicksilver essayistic style. In one of the most exuberant passages of Low Life, Luc Sante calls Manhattan “a creature, a mentality, a disease, a threat, an electromagnet, a cheap stage set, an accident corridor. It is an implausible character, a monstrous vortex of contradictions, an attraction-repulsion mechanism so extreme no one could have made it up.” Lopate has spent nearly six decades living in that vortex and grappling with its contradictions by cultivating an essayistic style that’s lyrical and historical, elegiac and pragmatic, steely and serene, affable and brash. In Waterfront Lopate has enriched and refined his style by taking it quite literally to the vortex’s watery edge, and for anyone wandering along that shoreline, his book will be a lively and trusty compass.