As a walking tour guide and historian, I’ve discovered that an often-overlooked source for understanding New York City is old guidebooks. Whether it’s something as mundane as addresses of railway depots—did you know there was once one facing City Hall Park?—or as interesting as finding out that Benjamin Franklin conducted electrical experiments from the steeple of the old Dutch Church (which was, fittingly, later converted into the main post office), guidebooks often contain nuggets of information left out of more conventional histories.

One day, as I was reading the 1866 edition of one such guide, Miller’s New York As It Is; or Stranger’s Guide to the Cities of New York, Brooklyn, and Adjacent Places, I noticed an addendum at the back of the book called "Supplemental Hints." The book had come out sporadically since 1859; in this edition, author/publisher James Miller had included, for the first time, suggestions for how visitors could create their own walking tour of the city.

Miller—mindful that a "tour of the entire city would be a too arduous performance for a pedestrian"—instead advised his reader "to limit his perambulations to Broadway, from the Bowling Green to Union Square."

What would it be like, I wondered, to walk the streets of New York with an 1866 guidebook in my hand? How much of Miller’s city still exists? I downloaded New York As It Is onto my iPad and prepared to find out.

Before I left, I first wanted to see how Miller’s book compared with his competitors’. Though guidebooks to the city have been around since at least 1817, when Edmund Blunt published his Stranger’s Guide to the City of New York, the era around the Civil War saw a proliferation of titles.

Miller’s main rival seems to have been Lloyd’s Pocket Companion and Guide Through New York City, 1866-67, which is made up exclusively of seven walking tour itineraries. These walks were purportedly compiled by a native New Yorker named John Wetherby, though I have found no evidence that such a person ever existed. Wetherby’s first walking tour itinerary turned out to be very similar to Miller’s—a stroll up Broadway from Battery Park.

So I downloaded that book, too.

The Pocket Companion’s conversational style reminded me of a book I’d unearthed during my research into the history of West Broadway, a guidebook written before the Civil War. Titled Glimpses of New-York by a South Carolinian (Who Had Nothing Else to Do), the book came out in 1852 with the goal of proving to Southern readers that New York was just as wretched as they expected it to be. It seemed like the perfect antidote to the native boosterism of my other two guides.

Then, because I couldn’t help myself, I downloaded another book called Phelps’ New York City Guide (1867). And then A Picture of New York (1848); The Stranger’s Hand-Book for the City of New York; or, What to See, and How to See It (1854); Nelson’s Guide to the City of New York and its Neighbourhood (1859); and Appleton’s Illustrated Hand-Book of American Travel: The Eastern and Middle States and the British Provinces (1860).

Finally, armed with more mid-19th-century guides than any reasonable person should read, I was ready to set out.

Seeing as how the Pocket Companion is not only exactly 150 years old, but also the only book in my arsenal entirely devoted to walking tours, I decide to use its "Walk the First" to structure my itinerary, supplementing from New York As It Is, Glimpses of New-York, and the other guides as necessary.

As I take the No. 1 train downtown, I read the introduction to the Pocket Companion, which begins with a section called "Why It Was Written." After the narrator introduces himself as John Wetherby, he announces:

Walking is my delight. Often, stick in hand, do I start out on a morning, and roam about the whole long day, viewing the various places of interest, and noting down in my memory any curious or quaint story.

Wetherby realizes that his vast stores of knowledge would help visitors; lo and behold, an old friend, Jonathan Griggs, immediately shows up at his doorstep looking for a place to stay. Wetherby seizes on the opportunity to show his friend around; for a week, they set off on a different walk each morning, each becoming one of the Pocket Companion’s seven itineraries. Each walk is told as a conversation between the two men: Griggs, the country rube, asks all sorts of leading questions; Wetherby, of course, has all the answers.

"Walk The First" begins with Griggs and Wetherby deposited by horse-drawn stagecoach at Battery Park; unable to catch a stagecoach, I instead exit the subway at South Ferry and make my way to their first stop: Castle Clinton, then known as Castle Garden.

"I have heard of that before," Griggs tells Wetherby in the book, in an example of what will become their usual banter. "When Jenny Lind came to this country, she made her first appearance there." The book goes on to note "Griggs was delighted at his knowledge."

Wetherby replies:

"It was one time a fortification, but now it is devoted to more peaceful pursuits, being used as an emigrant depot." "Is that where all the emigrants land?" "Yes, every one of them. It is an excellent institution, and saves many a poor person from being robbed of all they possess in the world." "How?" "In former times the emigrant, as soon as the ship touched the dock, was dumped out upon the pier like so much merchandise, and made to shift for himself the best way he could. Sharpers were on the watch for him; he was robbed and cheated in every direction; and in a few hours he had not a cent left to bless himself with."

Most of the Pocket Companion continues in this fashion: Griggs is inordinately proud of himself for knowing some fact or figure about New York, but Wetherby is always there to prove he knows more.

It would be the equivalent today of having the subway run at grade level down the middle of the street.

These conversations are generally accurate. Castle Clinton was a fortification, built for the War of 1812. As a theater, it did host Jenny Lind; it was then the state-run Emigrant Landing Depot, which it would remain until 1889, when the federal government took over the job of processing incoming passengers.

Following Griggs and Wetherby’s itinerary, my next stop is Bowling Green, where there "was once a leaden statue of George III, which, at the commencement of the Revolution, was torn down and moulded into bullets."

Griggs, however, is more fascinated by the sheer number of horse-drawn omnibuses surrounding the small park than in hearing about King George. It can be hard for the modern New Yorker to imagine just how much worse traffic in the city was 150 years ago, but—as Wetherby points out—"nearly seven hundred stages [went] up and down Broadway daily," with each one making "ten trips per diem" for a total of "seven thousand stages daily for the use of our citizens." It would be the equivalent today of having the subway run at grade level down the middle of the street.

Fourteen years earlier, the Southern author of Glimpses of New-York had noted that "[Broadway] has become quite difficult to cross ... and whenever attempted it is at the peril of your life or limbs." The traffic problem would take generations to improve. In 1885, nearly two decades after the Pocket Companion’s release, engineer Francis V. Greene still counted nearly 8,000 horse-drawn vehicles pass him as he stood at the corner of Broadway and Pine Street.

But the Pocket Companion’s Griggs has little time to ponder the wondrous traffic; soon Wetherby is whisking him up to the top of the steeple of Trinity Church. Though I follow in their footsteps, I have to be content with the view from across the street—the steeple has been closed to visitors since 1883.

Back in the 1860s, a visit to Trinity’s spire—then the tallest tower in the city—was the one constant in every guidebook. As Miller notes in New York As It Is:

By way of introduction to the city in detail, we recommend the visitor first get a bird’s-eye view of it from the steeple of Trinity church. A view from this elevation, over 320 feet in height [Note: the spire is only 284 feet tall], affords a good idea of the general extent and topography of the city. The tower is accessible to the public any time of the day excepting the hours devoted to divine service ….

From their perch, Wetherby waxes poetic in the Pocket Companion:

As we … cast our eyes upon the stores and warehouses, many of them filled to depletion with the products of every nation upon the earth, brought hither by those very ships we now see fringing the shore, we can scarcely believe that a little over 230 years ago the whole of this island was purchased of the Indians for a sum equivalent to twenty-four dollars. Yet so it was.

When the Pocket Companion came out, that $24 figure was only about four decades old, so it’s notable how quickly it became enshrined in the city’s lore. The dollar amount was calculated by state historian John Romeyn Brodhead in 1826, and was, even then, essentially meaningless. It’s better to think of Colonial prices in terms of purchasing power; what the Dutch paid for the island of Manhattan in 1626 would have also bought them 2,400 tankards of beer—a bargain, but not $24.

Up to this point, Miller’s walk in New York As It Is and Wetherby’s have been basically the same. Miller doesn’t bother with Castle Garden (which he derides as having "little architectural beauty to boast"), but starts at Bowling Green before heading to Trinity. He then suggests the natural detour down Wall Street. Wetherby, by contrast, won’t be diverted from his route up Broadway, promising Griggs they’ll come back another day.

I choose to follow Miller’s route, first heading down to Federal Hall, then known simply as the United States Treasury. Built in 1842 by the architectural firm Town & Davis, it served as the federal Custom House before that department moved down the street to the old Merchant’s Exchange at 55 Wall Street in 1862. Miller steers his visitors from the Treasury to 55 Wall and then back to Broadway to see the various banks at the heart of the Financial District. In the middle of the work day, Wall Street was even then one of the city’s most crowded thoroughfares: Miller warns walkers that at "every moment" they "are in danger of being jostled or pushed aside by … crowds of pedestrians, all eagerly in pursuit of something."

As I return to Broadway, I pick up Wetherby’s narrative; he is busy showing Griggs around Trinity’s cemetery, including the graves of Alexander Hamilton, Commodore James "Don’t Give Up the Ship" Lawrence, and Lieutenant Ludlow. The first two I’ve visited often, but I confess that I had to look up the last one; it turns out Ludlow was Lawrence’s second-in-command on the USS Chesapeake and is buried alongside his commanding officer.

After admonishing Griggs not to give to beggars on the street but instead to charity (some things never change), Wetherby has to rescue his companion from nearly being trampled by a horse. The entire incident seems to have been concocted for two reasons: one, as a warning for out-of-towners to look where they’re going; two, so that Wetherby can introduce Griggs—and his readers—to the first of many stores the two will visit on their walk: Knox’s Great Hat and Cap Establishment.

I have no idea if the Pocket Companion’s publisher, Thomas Lloyd, solicited these advertisements as product placements, but as Wetherby and Griggs make their way up Broadway, they stop into everything from a billiard table factory to a drugstore to two different sewing machine shops. When Wetherby describes these spots to Griggs, he’s sometimes quoting verbatim from the advertisements. Alas, though the modern-day walker can visit many trendy shops along the same stretch of Broadway—shops that continue to lure tourists from around the world—none of the places mentioned in the Pocket Companion still exist, at least not in their 1866 locations.

Leaving Knox’s with a new cap, Wetherby and Griggs stop at St. Paul’s Chapel, having first glanced at the still-under-construction New York Herald building across the street. What Wetherby fails to mention is that the site of the Herald had for many years been occupied by P.T. Barnum’s American Museum, which burned to the ground in a spectacular fire a year earlier, in 1865. (Earlier guidebooks grudgingly acknowledge Barnum’s success; as Francis’s New Guide to the Cities of New-York and Brooklyn put it, "the wonders contained in which building none but a Barnum could either have collected … or can adequately describe.")

It’s at this spot that I realize that using the Pocket Companion as my guide was the right choice. The walking tour in Miller’s New York As It Is would have had its readers searching in vain for Barnum’s Museum. James Miller, I later discover, wasn’t very good at updating his guide. New York As It Is continued to be published through the early 1880s, but critics complained that he was still describing the city as it had looked in 1859, when the first edition came out.

At St. Paul’s, Wetherby and Griggs visit George Washington’s pew, along with the tombs of General Richard Montgomery, who died at the Battle of Quebec in 1775, Robert Emmet ("the Irish patriot"), and actor George Frederick Cooke, all of which are still visible in the church and yard, but none of which draw many people—certainly not compared to the crowds that flock to Alexander Hamilton’s grave down the street.

After a quick stop at the now-demolished Astor Hotel—where Wetherby writes that "the thirsty can bibulate and the hungry can be fed (if their impecuniosity is not too great to prevent them)"—they continue to City Hall Park and its Croton Aqueduct fountain (replaced in 1872). In the bad old days, Wetherby tells Griggs,

visitors from the country were often fleeced by sharpers when they attempted to enter any one of the park gates. One of these scamps would accost the stranger and demand money for admittance, which the stranger, not being accustomed to the ways and manners of New York, would incontinently pay.

City Hall Park’s poor reputation would endure for over a century. As recently as the 1980s, Parks Commissioner Henry J. Stern was calling it a "shabby, rundown patch of grass and roots surrounding a parking lot." Part of the park’s downfall came in 1869, when the lower quadrant was taken over by construction of the new main post office, finished in 1880. The post office stood until 1938 (when it was superseded by the current building on Eighth Avenue), and it took 50 years from its demolition for the park to recover.

The next stop in the Pocket Companion is City Hall itself, which, like Trinity Church, is one of the "must-see" sights of Lower Manhattan in every 19th-century guidebook. In New York As It Is, Miller calls the building, constructed at great expense from 1803 to 1810, "an imposing edifice," but saves most of his praise for the clock in the cupola. Wetherby similarly tries to impress his visitor with the massive timepiece:

"New York time is governed by that clock. I presume that every man who possesses a watch, and whose business is down town, regulates his timepiece by it. It originally cost $4,000." "Four thousand dollars!" ejaculated the astounded Griggs; "a good price for a clock." "True; but then it’s a good clock for the price. The main wheels of it are two feet six inches in diameter, and the pendulum-bob weighs three hundred pounds." "Gracious goodness! Three hundred pounds!" muttered the astounded Jonathan.

Nearly all of this conversation seems like it is cribbed from New York As It Is. Indeed, despite Wetherby’s early boast about how much he knows about New York, the deeper one delves into the Pocket Companion, the more apparent it becomes that the material is cobbled together from other guidebooks, and—like the language lifted directly from advertisements—put into quotes as dialogue between the two characters.

(By the way, the clock and cupola were restored and rebuilt in 1998 during the Giuliani administration.)

Before leaving City Hall Park, Wetherby takes Griggs to see what he calls "the new City Hall … larger and more commodious than the present one."

New City Hall? I knew that at the turn of the 20th century, the city flirted with the idea of building a new government building, which ultimately became Surrogate’s Court instead. But I had never heard of a new City Hall under construction in 1866.

"The corner-stone," Wetherby explains, "was laid in 1862, and there is no doubt that 1867 will see the completion of the building."

Wetherby is actually talking about the Tweed Courthouse, the greatest boondoggle in New York’s history and the building that ultimately brought down William M. "Boss" Tweed. In hindsight, Wetherby’s prediction that the building would be finished in 1867 seems like impossibly wishful thinking. By the time Tweed was arrested for fraud in 1871, the exterior of the building was standing but little else had been finished.

The frauds involved in this project are legendary: for example, Andrew Garvey, who was the building’s plasterer, was paid $133,187 for two days’ work. That sum was more than half the building’s original budget. After Tweed’s downfall, architect Leopold Eidlitz expanded and finished the structure, which now serves as the headquarters for the city’s Board of Education.

Up to this point on my walk, with the exception of the Astor Hotel, the New York Herald building, and the old fountain in City Hall Park, everything on Wetherby’s itinerary still stands. Miller’s book would have shown me some banks and newspaper offices that are now gone, but it’s still remarkable that what was considered noteworthy in the Financial District 150 years ago are the same sites people visit today.

North of Chambers Street, however, the tours fall apart. While A.T. Stewart’s Marble Palace (a "great emporium of costly shawls, satins, silks, brocades, &c.") still stands at the northeast corner of Broadway and Chambers Street—filled mostly with New York City government offices—almost all of the other locations that New York As It Is and the Pocket Companion point out are long gone.

There are a couple of exceptions. Wetherby and Griggs stop for lunch at Taylor’s Saloon, which was housed in the ground floor of the International Hotel at the corner of Franklin Street. Wetherby explains it is "the favorite resort … of the fashion and elite of New York," pointing out the variegated marble flooring and the $3,500 ceiling embellishments. Alas, Taylor’s is all but gone today. When the building was "renovated" in 2010, only a smattering of original architectural details were preserved.

Sometimes history repeats itself; though the specific store may be gone, as Wetherby and Griggs stroll through what we call Soho, Griggs opines, "here on Broadway a man can obtain everything he wants. Let him make known his wishes, whether an article of luxury or necessity, and he can be supplied without leaving the street."

In New York As It Is, James Miller points out Haughwout & Co., which today stands as one of the finest cast-iron structures in Soho; both books note the St. Nicholas Hotel, one small portion of which (521-523 Broadway) today houses a Lady Footlocker, but the next real point of interest that I can actually step inside is Grace Church, at the corner of 10th Street. Miller first praises the James Renwick-designed structure as "the most ornate of the ecclesiastical buildings" in the city before noting it contains "a little too much theatrical glitter in the interior, to comport with the chastened solemnities of religious worship."

Both tours then bring walkers to the equestrian statue of George Washington in Union Square. As Wetherby tells Griggs, "That is the bronze statue of the immortal Washington. It was designed and executed by Mr. [Henry Kirke] Brown …. This one cost upwards of $30,000. On the opposite side of the square … a companion statue of Abraham Lincoln is to be erected."

The Washington statue, erected in 1856, is today the oldest statue in the New York City Department of Parks and Recreation’s collection of public art. Brown’s companion Lincoln statue now stands mid-park, near 16th Street, on a modest base; however, when it was unveiled in 1870, it stood on a massive stone pedestal that the New York Times said was made from "the largest stone ever quarried in America."

Union Square marks the end of Miller’s walk in New York As It Is; Griggs and Wetherby—after stopping in the Steinway piano showroom—extend theirs a little farther up Broadway to Madison Square. However, other than the "10 acres … of noble trees" and the General Worth monument, the sights they take in around this small park—home then to fancy houses and upscale hotels—are wholly different from what I see today.

My walk from Battery Park to Madison Square has covered 3.3 miles of Broadway. And I have to admit, just like Griggs tells Wetherby (with "an air of profound wisdom") at the end of "Walk the First": "I am getting tired."

I have half a mind to explore the other six walks in the Pocket Companion on subsequent days, but with the exception of "Walk The Second," which saunters through Central Park, the other itineraries mostly turn out not to be full-fledged walks, but catch-all explorations of various categories of institutions.

"Walk the Third" is titled "Public and Benevolent Institutions," and while the Pocket Guide continues the fiction of the two men walking and talking, it doesn’t seem like a genuine itinerary any person would ever want to carry out. "Walk the Fourth" is newspaper offices and seems more plausible, since almost all of them were clustered near City Hall, but "Walk The Fifth" ("Public Amusements") gives up any pretense of being an actual guided itinerary. Wetherby confesses: "there is no more pedestrianism in it than there is grass on Broadway."

"Visitors from the country were often fleeced by sharpers when they attempted to enter any one of the park gates. One of these scamps would accost the stranger and demand money for admittance, which the stranger, not being accustomed to the ways and manners of New York, would incontinently pay."

"Walk the Sixth" covers wharves and shipping; it’s a fascinating read, but would be impossible to recreate today; "Walk the Seventh" is also not a walk—it’s a list of churches "so numerous it would be impossible to visit them all in one day."

I turn, instead, to Glimpses of New-York and head to Foley Square, once the edge of the notorious Five Points. Like modern guidebook writers, who generally don’t steer readers to high-crime neighborhoods—or even to immigrant enclaves outside of Manhattan’s Chinatown, for that matter—19th-century authors tended to avoid mention of the Five Points. But William Bobo, the "southern gentleman" who composed Glimpses, revels in pointing out New York’s underbelly.

Sitting on a bench near the courthouses, I read Bobo’s introduction to the area:

Have you got a good supply of cigars? — if not, get some, as we shall need them while prowling about among the filthy cellars and the malaria which envelopes that region of the city. Let us go up Broadway to Anthony-street [today’s Worth Street], thence east down Anthony to the Points, it being only three short blocks, passing Elm and Centre streets to the citadel of this notorious rendezvous of crime and poverty.

Around me, office workers and people taking a break from jury duty enjoy the late spring sunshine. There’s no crime and little poverty in sight.

Bobo continues:

As we approached … every house became worse in appearance after we left Broadway, till we crossed Centre-street. There it sinks into a sameness — like the degrees of crime, till you reach infamy, positive and hopeless. You begin to see the squalid, roisterous-looking, drunken females, sitting upon the door-steps, or standing round the counter of a drinking hole. The groups are from three to four in number, not more. The children, poor little fellows, half naked, winter and summer, it is all the same, are seen moving from place to place, with a make-shift of a toy, or a piece of bread or a bone in their clutches, gnawing it like young dogs around a kitchen yard ….

Though typical guidebooks ignored it, Five Points fascinated mid-19th-century writers. Tyler Anbinder, whose survey of the area’s history remains definitive, calculated that it was the most "thoroughly studied" place in America at its peak. That makes it all the more remarkable that, today, few visible traces remain.

I stand on the corner of Worth and Baxter Streets, the lone "point" of the five-pointed intersection that lent its name to the area. There’s no plaque or sign. In fact, the neighborhood was already so thoroughly destroyed by 1928 that when William Asbury wrote Gangs of New York, he placed the intersection one block too far east. Martin Scorsese’s film adaptation does the same thing, as do the countless tour guides that I see wending their way through the neighborhood.

Five Points isn’t totally gone, however. At the corner of Mosco and Mott Streets stands the Catholic Church of the Transfiguration, originally built in 1801 as a Lutheran parish. It predates the Five Points by decades and has stood sentinel all this time as Five Points, Little Italy, and Chinatown have ebbed and flowed around it.

Few guidebooks paid attention to this church—today, the third oldest in Manhattan—both because of its undesirable location and because Roman Catholic parishes weren’t seen as being as worthy as Episcopal or Presbyterian houses of worship. That’s too bad, because by some accounts Transfiguration was among the largest parish churches in the world 150 years ago, with some estimating over 20,000 members on its parish rolls.

Even in the 1850s, Bobo notes changes were afoot in the neighborhood. He observes the "missionaries and the mechanics" who were building up the area. "The glory and the shame of the Five Points," he notes, "are gradually departing, and the advent of better times is close at hand."

By the time the Pocket Companion was released in 1866, Wetherby could point out to Griggs all the changes:

"‘Five Points’ is not what it used to be …. Now a person can visit there without fear of molestation; fights and broils are the exception — not the rule …. [I]t is a little elysium, compared to what it was some fifteen or twenty years ago." "What has wrought this change?" "That building!" and I pointed to House of Industry.

The Five Points House of Industry, established in 1850, stood at 155-159 Worth Street facing Paradise Square, the heart of the neighborhood. There’s no denying that the House of Industry served the community, providing education for children. Those "found sufficiently worthy" (according to the Pocket Companion) were then shipped out of the city "so as to wean them from old associates."

The erection of the building itself was a change on the face of the neighborhood; more importantly, by pushing immigrant children out of the neighborhood—or at least raising them to be more like their Protestant benefactors—the House of Industry altered the very nature of the Five Points. Soon the name would be gone, followed by the wholesale dismantling of the neighborhood, first with the construction of Columbus Park in 1892, then with the clearing of Foley Square and the building of the courthouses and other government offices. Five Points became the Civic Center. The maps were changed; the history was forgotten.

Yet some of that history still lingers on. Sometimes it’s hidden in an out-of-the-way church like Transfiguration; sometimes it exists only in the pages of these guidebooks. The tour in Miller’s New York As It Is begins with a summary that might well be written in any book about the city today:

Persons who, for the first time, visit a great city like [New York] doubtless fancy themselves in a very Babel of excitement and confusion …. No city in the New World is so truly cosmopolitan in its character as New York; consequently it presents almost endless variety of objects of interest for the visitor. It is difficult to describe its many-hued aspects, for it is, in fact, an epitome of the civilized world; and the physical as well as the moral aspects of the city present a like complicated character.

It’s that "complicated character" that makes the city—even as prices soar, gentrification spreads, and corporate chains replace local industries—worth exploring.

Editor: Sara Polsky