Founding Father

FEDERALIST, n. An appellation in America, given to the friends of the constitution of the United States, at its formation and adoption, and to the political party which favored the administration of President Washington.


Counting His Way across America

COUNT, v.t. To number; to tell or name one by one, or by small numbers, for ascertaining the whole number of units in a collection; as, to count the years, days and hours of a man’s life; to count the stars. Who can count the dust of Jacob? Numb. xxiii.

On Monday morning, May 2, 1785, as the melting snow pushed the water in the Connecticut River to dangerous heights, Webster headed off to the other end of America.

By midafternoon, he had completed the first leg of his southern journey, the familiar forty-mile trek to New Haven. Upon his arrival, Webster headed directly for Chapel Street, where he spotted Yale president Ezra Stiles. Webster’s former classmate, Josiah Meigs, who had recently completed a stint as Stiles’ science tutor, was about to inaugurate the age of American air travel. Like Stiles and the rest of the crowd gathered on the Green, Webster, too, was eager with anticipation.

Webster looked over at the eleven-foot-wide sphere that was destined for the sky. Made of paper, the balloon was decorated with a figure of an angel, which in one hand bore a trumpet and in the other, an American flag and the motto “Nil intentatum nostri liquere poetae” [There is no theme that our poets have not tried]. The immortal words from Horace’s Ars Poetica were also painted in seven other languages, including Greek, Hebrew, Chaldee and English.

Shortly before three o’clock, Meigs, now publisher of the new newspaper The New Haven Gazette, began stuffing the kindling shavings into the one-foot hole at the base of the balloon. A few minutes later, the flaming metal basket took off.

Craning their necks, Webster and the rest of the spectators looked straight up.

The balloon traveled just over the weathervane of the Brick Church on the Green, falling down on Mr. Marshfield’s house nearby. But soon Meigs was gearing up for a second launch. This time, the pyramid of fire rose a few hundred feet higher, but its descent was much more rapid; sensing that New Haven was under attack, some militiamen accidentally shot three balls right through it.

In his diary, Webster accentuated the positive, “See a balloon ascend ingenuity of Mr. Meigs. It rises several hundred feet.”

New Haven was just a one-night stopover. Within a few weeks, Webster was zigzagging across the South, where his daily life would be filled with uncertainty. To finance his travels, he would have to find work as he went along. A foreigner in his own country, he would battle headaches, boredom and despair. He would miss his native New England. Early in 1786, he noted in his diary, “An eminent merchant in Alexandria informed me that of 50 planters in Virginia who sold him tobacco, only 4 or 5 could write their names but made a mark on the receipts. O New England! How superior are thy inhabitants in morals, literature, civility and industry.” Though Webster rarely mingled with the hoi polloi—he met the most prominent people in nearly every town he visited—the feelings of alienation persisted.

After completing his southern tour in mid-1786, Webster went back on the road to give another round of talks on the English language in the Middle (mid-Atlantic) and New England states. While he would dutifully record his thoughts about his two-year trans-American odyssey in his diary, in his public writing he said little—with one exception. In 1788, at the end of one of his articles, Webster appended the list:


As he traveled across America in 1785 and 1786, Webster would personally count every house in its major towns and he wanted the world to know his final tallies.


Webster reexamined his house counts before publishing the final list in his 1788 article in The American Magazine. While here he records a total of 4,600 houses in Philadelphia—including an additional eighty-two “allowed for mistakes”—in his final tally, he reported 4,500.

This compulsion to count links Webster with his lexicographical brethren. As a teenage medical student in Edinburgh in the early 1790s, Peter Mark Roget of Thesaurus fame would count all the steps he took to class every day. Likewise, Webster’s hero, Samuel Johnson, once remarked that he took recourse in “the study of arithmetic” whenever he felt “disordered.” While heading toward his breakdown at Oxford, Johnson produced a chart in his journal listing the total number of lines of Latin poetry he would translate in a week, month and year, if he did a certain number per day (say, ten, thirty or sixty). For Webster, too, counting could help mitigate the angst that lurked within. In the mid-1780s, most of America’s biggest metropolitan areas were still small enough that he could count all the houses during one leisurely walk. But this one-man data collection agency didn’t focus just on America’s residential real estate. For the next few years, an often nervous and distraught Webster kept track of a wide range of data, including demographic information, temperature readings, wind currents and voting records.

THE MAN WAS BLIND, yet he was an international authority on optics.

His name was Dr. Henry Moyes. At a few minutes before seven on the evening of Monday, May 16, 1785, the professor was standing before a packed house of nearly two hundred at Baltimore’s St. Paul’s Church, located in the center of town, about a mile north of the harbor. The eminent scientist was then barnstorming across America’s major cities, giving lectures four nights a week. His twenty-one-lecture course in Baltimore, for which he charged gentlemen a guinea and ladies a half guinea, covered “all those astonishing discoveries which must forever distinguish the 18th century.”

Seated in a pew at the front, Webster was eager to hear Moyes talk about light, the subject of his remarks that night. A year earlier in Boston, Webster had attended Moyes’ lecture on electricity, which he found instructive. And having been introduced to the professor the day before, Webster was most impressed, characterizing America’s newest celebrity as “blind, but sensible.”

Webster had arrived in Baltimore just two days earlier. From New Haven, he had sailed to New York City, where he stopped off just long enough to have tea with Colonel Aaron Burr, then a young trial lawyer, at his town house on Maiden Lane. At the time, Webster knew Burr’s new wife, Theodosia Prevost, better than the colonel himself, as back in Sharon, Webster had taught the two boys from her former marriage. En route to Baltimore, Webster also passed through Philadelphia, where he enjoyed a lively dinner with his cousin, the author and merchant Pelatiah Webster, who commented favorably on his Sketches. Webster also considered his older relative, a 1746 Yale graduate, “very sensible,” and the two writers would remain close until the Philadelphian’s death a decade later.

Though Baltimore was a boom town, Webster felt uncomfortable in his new surroundings. The housing stock of Maryland’s commercial center, which had doubled since 1782, was, as Webster would personally determine that fall, approaching two thousand units. And rents near the harbor had risen to a guinea per square foot. However, this town of some ten thousand residents was still run-down and dirty. Only its main thoroughfare, Market Street (today Baltimore Street), was paved. The French politician and writer Jacques Pierre Brissot noted a few years later, “the great quantity of mud after a rain, everything announces that the air must be unhealthful. However, if you ask the inhabitants, they will tell you no.” Despite his uneasiness in Baltimore, Webster would make it his base of operations over the next six months.

Webster was often sad and homesick. Missing the orderliness of Connecticut, he longed for news from his friends and family back in Hartford. That summer, he would write in his diary, “Lament that I am in Baltimore.” To keep up his spirits, Webster would surround himself with fellow New Englanders such as Dr. James Mann, a prominent army surgeon during the Revolution, who accompanied him to Dr. Moyes’ lecture that night.

As Webster well knew, Moyes had a distinguished academic pedigree, despite having lost his sight at three due to smallpox. As a boy in Kirkaldy, Scotland, Moyes had accompanied the economist Adam Smith, then writing his masterpiece, Wealth of Nations, during his afternoon walks. Through Smith’s prompting, Moyes had studied under two of the world’s greatest philosophers, those architects of the Scottish Enlightenment, Edinburgh’s David Hume and Glasgow’s Thomas Reid.

As Moyes began to speak, Webster was struck by the clarity of his language and exposition. The doctor divided his lecture into six parts. After discussing ignition and combustion, he moved on to the production of light. With help from his assistant, a Scotsman named Mr. Frasier, he then performed an experiment demonstrating the materiality of light. The professor, who himself could not see the light of day, concluded by discussing sunlight and light particles. Between his scientific points, Moyes interspersed moving anecdotes. Describing his reaction when he was once thrown off a stagecoach, Moyes observed, “I was quite at home in the dark ditch. The inversion of the order of things was amusing. I that was obliged to be led about like a child, in the glaring sun, was now directing eight persons to pull here and haul there.” His cheerful disposition moved Webster. He was not alone. Reviewing Dr. Moyes’ performance, The Maryland Journal reported, “Charmed to see a gentleman whom cloud indeed . . . . surrounds, . . . his auditors have expressed the highest satisfaction in his abilities and the agreeable manner in which he delivers himself on these truly admirable and important subjects.”

The next day, May 17, Webster moved into Mrs. Sanderson’s lodging house off of South Street, where Dr. Mann and another New Englander, Josiah Blakely, a Hartford merchant, were also staying. That night, he went back to St. Paul’s to hear Dr. Moyes lecture on phosphorus. A week later, after returning from his overnight stay in Mount Vernon, where he had passed on a copy of his Sketches of American Policy to General Washington, Webster caught a few more installments of the professor’s lecture series. On May 24, Webster wrote in his diary, “The Dr. has 190 hearers generally.” Impressed by the size of the crowds, Webster began toying with the idea of emulating Dr. Moyes. To pay for his book tour, he would soon become America’s first homegrown celebrity speaker.

ON SATURDAY, MAY 28, Webster made provisions to take his copyright campaign to the Deep South. His ultimate destination: the South Carolina port city of Charleston (known as Charles Town until the British evacuation at the end of the war).

Catching the sloop George from Baltimore on May 30, Webster stopped off at Norfolk, Virginia, on June 1, where he was delighted to eat cherries for the first time—the fruit would later be a mainstay of his New Haven garden. He was surprised by the fertility of the soil, in which green peas were so plentiful. But after dropping off three dozen spellers with a local bookseller, he couldn’t wait to get out of town, writing in his journal, “Little attention is paid to religion, education, or morals. Gentlemen are obliged to send their children to the northward for education. A shame on Virginia!” Though Webster didn’t complete a count of Norfolk’s houses, he came up with a rough estimate, adding that the town “consisted of two or three hundred houses well built of brick; but it was burnt by the British troops and has not recovered its former elegance.” Squalls alternating with calm seas made sailing on to Charleston trying. This leg of the trip, which was supposed to take a few days, lasted a few weeks. As the boat stalled, Webster’s nerves started to fray. On June 14, he observed, “Wind continues contrary. O how disagreeable! We make but 10 or 12 miles a day.” Whenever a favorable breeze came along, Webster and his fellow passengers would express relief by singing and dancing on the quarterdeck.

Soon after reaching Charleston at 8 a.m. on Sunday, June 26, Webster dashed off to hear Parson Smith’s sermon at St. Michael’s Church. After the services, Webster stayed for a musical performance by Miss Maria Storer, an English opera singer then giving a series of concerts in Charleston. With the local newspaper, The Columbia Herald, criticizing her for singing Italian songs, which its correspondent called “at best an exotic entertainment,” she had recently switched to more traditional fare. But even so, Webster objected. “Miss Storer,” he recorded in his journal, “sings part of Handel’s Oratorio—very odd indeed! A woman sings in public after church for her own benefit! I do not like the modern taste in singing!” Slipping a quarter into the plate, Webster grudgingly acknowledged her talent, “She sung well in the modern taste, but I cannot admire it.”

Over the next week, Webster met with a host of local dignitaries including General Christopher Gadsden, who had been a delegate to the Continental Congress and a brigadier general in the Continental army, and Charleston’s first mayor, Richard Hutson. The town’s inhabitants appealed to him: “The people in Charleston are very civil and polite. They behave with great decency in church. The slaves are kept in good order, they are remarkably attentive in church.”

Webster was pleased to celebrate America’s ninth birthday in Charleston. Independence Day festivities began precisely at one o’clock in the afternoon as the militia fired thirteen volleys, one for each state in the union. Afterward, Governor William Moultrie hosted a lavish dinner at the City Tavern. Fourteen toasts were drunk, most of which struck a deep chord with Webster, such as number ten, “Unanimity to the American States,” and eleven, “May the arts and sciences flourish in America.” After dinner, Webster and the other celebrants endured a brief scare, as one of the thirteen hot air balloons went up in flames as it headed toward the beef market. The fire was quickly extinguished, and no further balloons were launched. As Webster put it in a letter to his publisher, Hudson and Goodwin, the fire “put an end to this boyish amusement.”

That evening, Webster walked back over to St. Michael’s Church to get a view of the city from its steeple. Modeled on the English churches designed by Christopher Wren, St. Michael’s, completed in 1761, stood on the site of a seventeenth-century Anglican church, the first built south of Virginia. The tower featured an exquisitely wrought clock and eight bells (which the city’s Loyalists had had shipped back to England during the war). “They have,” Webster noted in his diary, “a good chime of the bells.”

After walking up the nearly two hundred steps to the top of the steeple, Webster looked out and was impressed by the town’s orderly layout: “Charleston is very regular; the most regular of any in America, except Philadel and New Haven.”

Charleston would soon return the compliment. The following day, Webster donated three hundred copies of his Grammatical Institute to the Mt. Sion Society, which administered South Carolina’s newly created Winnsborough College. Later that summer, the society’s secretary published a letter of thanks to Webster in The State Gazette of South Carolina, which included a glowing tribute, “That your exertions for the advancement of useful knowledge may meet with merited success and applause must be the wish of every friend to science in the rising states of America.” The speller would soon be a staple of education throughout South Carolina and, when the state’s copyright law passed a few months later, Webster would reap the profits.

As Webster got ready to leave Charleston, he reported to his publisher that his southern journey, though expensive, was “the most useful and necessary I ever undertook.”

AT SIX O’CLOCK ON WEDNESDAY, October 19, Webster fought off the rain to make his way to Baltimore’s First Presbyterian Church on Fayette Street.

Three days earlier, Webster had celebrated his twenty-seventh birthday. With his efforts to burnish his national reputation proceeding slowly, the fiercely ambitious author was feeling that life was passing him by. In his diary, he articulated his fears: “The revolution of a few years sweeps us away . . . . a few revolutions more with accelerated motion will turn me off the stage.”

Webster’s last few months in Baltimore had been rocky. The May advertisement in The Maryland Journal announcing his intention of opening a language school had attracted little interest. Forced to find another means of support, he taught singing according to a “regular scientific method.” And with the locals short of cash, he was forced to accept articles of clothing—gloves, shoes, slippers and silk stockings—for his tutelage. Though Webster managed to “astonish all Baltimore with ten scholars,” his heart wasn’t in his singing school. In early October, he got into a nasty “miff” with a singer by the name of Mr. Hall. “People in Baltimore,” he lamented in his diary, “have not been accustomed to my rigid discipline.” What’s more, his voice was losing its timbre. Regarding his instruction at his school on October 15, he was forced to acknowledge, “Sing bad this evening.”

In early October, the ever resourceful Webster sought to become the “American Dr. Moyes.” He, too, would now try to fill up lecture halls night after night.

Fortunately, Webster had recently gathered some new material on which he could draw. During a lonely weekend in late August, when he was feeling bored and disgusted with Baltimore, he had picked up his pen. As was often the case, emotional distress prompted a burst of creativity. As he later recalled, “While I was waiting for the regular sessions of the legislatures in those states which had not passed laws for protecting literary property, I amused myself in writing remarks on the English Language, without knowing to which purpose they would be applied.” Now, nearly two months later, he had figured out a way to make use of these musings.

Webster got to the church at six thirty, just as the doors opened. The five lectures that he was slated to give over the next week would all begin at seven. For the entire series, he charged seven shillings, sixpence. The fee for one lecture was a quarter.

Over the last few months, Baltimore’s First Presbyterian Church, a brick building recently expanded to accommodate fifty pews, had become like a second home. Using the space for his singing school, Webster had forged a cordial relationship with its pastor, the Reverend Patrick Allison. Called “a man of substance” by his peers, the erudite Allison had a taste for belles lettres, championing the work of British writers such as Alexander Pope and Joseph Addison. A personal friend of George Washington, Allison had served as chaplain for both the Continental Congress (during its brief tenure in Baltimore) and the Continental army. Webster and Allison were frequent breakfast companions, and a few days earlier over tea, Webster had given Allison a preview of his remarks.

Due to the inclement weather, the church was less full than he had hoped. Surveying the crowd of about thirty, Webster launched into his introduction: “The principal design of this lecture is to point out the origin of the English language. It begins, however, with general remarks on the importance of the subject—finds fault with the mode of education, which leads us to study the Hebrew, Greek, Latin, French and German languages, to the almost entire neglect of our own.” National pride would be Webster’s central theme. Americans, he argued, needed to devote more attention to one of their prized possessions, their own language. After giving a brief history of America’s tongue, Webster stressed its richness: “The English language is exceedingly copious; it is said to contain about 20,000 words. For the most part, the same idea, or nearly the same, may be expressed by two different words.”

While his listeners found Webster’s ideas engaging, if not enthralling, something about his manner rubbed them the wrong way. A veteran of the classroom, Webster was used to teaching children, not adults. Appearing to talk down to his audience, Webster came across as an annoying “know-it-all.” Catching Webster’s road show several months later in Philadelphia, the future secretary of state Timothy Pickering, who had been so moved by Webster’s speller, observed: “In truth there was so much of egotism, especially in a young man, apparent in his communications, as to prevent his hearers, receiving the satisfaction which might otherwise have been derived from many ingenious observations. . . . diffidence in a public lecturer, especially in a young man, [is] essential to the art of pleasing.” Diffident, Noah Webster would never be. To counteract his deep-seated social anxiety, he projected an unbecoming arrogance. A few years later, the writer William Dunlap, then Webster’s colleague in a New York literary society, satirized his awkwardness at the podium in Cuttgrisingwoldes, a play in which a character named Noah Cobweb exclaims:

My rules, my lectures, ev’ry night repeated 

Began to talk sometimes ere they were seated 

To show my zeal I ev’ry night held forth 

And deep imprest th’Idea of my worth 

Not soon forgot.

Webster was no affable crowd-pleaser like Dr. Moyes. Unskilled in forging human connections, he acted as if he were the only person in the room. Paradoxically, though he wasn’t sensitive to the perspective—or even presence—of his auditors, Webster would seek from them validation of his own worthiness. Admiration, he could never get enough of.

Not only was Webster’s manner overbearing, but he also didn’t have much of a stage presence. Speaking in a high-pitched monotone, his body language betrayed his inner turmoil. As one correspondent noted in The New York Packet in April 1786, “[Mr. Webster] appears to be enraptured when he speaks, but his raptures seem forced. The motions of his hands are rather unpleasing.” Though mortified by such observations, Webster would eventually acknowledge that his critics had a point: “That my delivery was ungraceful may be true. I was never taught to speak with grace. I know of no institution in America where speaking is taught with accuracy.” But to those who found fault with his use of language, he would not back down. For Webster, words were much more means than ends. He no longer had any poetic aspirations. To the New York writer who charged that his style was “divested of what are commonly called the flowers of rhetoric,” Webster shot back, “My design is of more importance. I wish to express my sentiments with clearness.” The accurate definer also poked holes in the phrasing of this reviewer, “How, Sir, can a style be divestedof what it never possessed? I suppose the correspondent meant destitute.”

Back at the First Presbyterian Church two nights later, before a slightly larger audience, Webster addressed errors in pronunciation in various local communities. While he professed not to play favorites, he tended to find fewer faults with the practices of New Englanders than with those of other Americans. As in his speller, so, too, in his lectures, Webster was obsessed with creating linguistic order in America. In a report back to his Baltimore landlady, Mrs. Coxe, a few months after this first round of lectures, Webster wrote that his plan was to “effect a uniformity of language and education throughout the continent.”

In his fourth Baltimore lecture, delivered on Monday, October 24, he took on poetry, discussing the rules of poetic verse such as line breaks and pauses. Ever the critic, Webster could not resist commenting on the slip-ups committed by the world’s greatest poets: “Homer, Shakespeare, and Milton are incorrect in regard to these pauses, but they are great geniuses; their souls were engaged upon sublimer subjects, which occasioned them frequently to overlook these minutiae.” In his last Baltimore lecture on October 26, Webster formulated his thoughts on education. Once again, he aimed to instill national pride: “The tour of America is more necessary to an American youth than the tour of Europe. Let it be remembered that a Washington, a Franklin, a Jay, an Adams and many other Americans of distinction were educated at home.” Webster was here talking as much about himself as about any hypothetical youngster, since he was then rounding out his own education by circling around America. In a rare moment of introspection, Webster later acknowledged that the lecture series first begun at Dr. Allison’s church may well have served his own emotional needs above all. “The readings were,” he acknowledged in 1789, “probably more useful to myself than to my hearers.”

While many listeners were irked by Webster’s style (or lack of it), few opposed his message. The night of his final Baltimore lecture, a relieved Webster wrote in his diary, “The lectures have received so much applause that I am induced to revise and continue reading them in other towns.” He would end up delivering them in a total of twenty towns. The substance was mostly the same, but as he moved back North, he sneaked into his literary musings some of the demographic information that he had unearthed while down South. On July 1, 1786, the day after Webster’s sixth lecture on English at the Connecticut State House in New Haven, Yale president Ezra Stiles recorded in his journal, “Last evening I attended Mr. Webster’s . . . last lecture. From him [Webster] I learn. Virginia: 650 thousands souls whites and blacks: ratio 10 to 11, i.e. ten Blacks to eleven Whites. Maryland: 90 thousand taxables, 150 thousand souls black, 200 thousand souls whites.”

An expansion of the ideas Webster first laid out in his Grammatical Institute, Webster’s lectures would form the basis of his 1789 book, Dissertations on the English Language. To Benjamin Franklin, then the recently retired president (governor) of Pennsylvania, Webster dedicated this volume, citing both the Doctor’s greatness as a scholar, but also his “plain and elegantly neat” prose. Franklin was the paragon of clarity Webster hoped to emulate. As in the speller and in his Sketches, here, too, Webster sought to unite Americans:

All men have local attachments, which lead them to believe their own practice to be the least exceptionable. Pride and prejudice incline men to treat the practice of their neighbors with some degree of contempt. . . . Small causes, such as a nick-name or a vulgar tone in speaking, have actually created a dissocial spirit between the inhabitants of different states, which is often discoverable in private business and public deliberations. Our political harmony is therefore concerned in a uniformity of language.

To combat local “pride and prejudice”—Webster lifted the phrase not from Jane Austen, then just entering her teens, but from novelist Fanny Burney—Webster recommended the adoption of national pronunciation standards. While not dictating specific norms, Webster urged Americans to eschew the lead of British authors who looked to the “stage.” Rather than relying on those versed in the dramatic arts, whom he abhorred, Webster suggested turning to the common man, since “the general practice of a nation is the rule of propriety.”

But Webster’s framing of this debate as one pitting the experts against the people was slightly disingenuous. After all, a principal objective of his Dissertations (and the lectures upon which the volume was based) was to promote his textbooks. And Webster also made a direct appeal to his fellow Americans to spend more money on his pedagogical tools: “Nothing but the establishment of schools and some uniformity in the use of books can annihilate differences in speaking and preserve the purity of the American tongue.”

LESS THAN TWO WEEKS after his final Baltimore lecture, Webster set off for Richmond to take his copyright campaign to Virginia’s state legislature. But he first stopped off at Mount Vernon, where he spent another night as Washington’s houseguest. As Webster left on November 6, Washington handed him letters of introduction to Virginia’s governor and the speakers of its two houses, which included the following remarks: “[Mr. Webster] is author of a Grammatical Institute of the English Language—to which there are very honorable testimonials of its excellence and its usefulness. The work must speak for itself; & he better than I, can explain his wishes.” Missing among those testimonials was one from Washington himself. In a letter dated July 18, Webster had asked Washington for “the addition of your name, Sir, to the catalogue of patrons.” The perennial straight shooter, Washington had declined, explaining that “I do not think myself a competent judge.” On purely literary matters, Washington preferred to remain outside the fray. Even so, the General understood the political implications of Webster’s textbooks and was eager to lend a hand.

Washington’s clout proved to be considerable. In Richmond, Webster renewed his acquaintance with James Madison and dined with Benjamin Harrison V, the longtime state legislator who had just ceded the governor’s office to Patrick Henry. (Harrison’s son, William, and his great-grandson, Benjamin, would both grow up to be U.S. presidents.) At Harrison’s suggestion, Webster gave his lecture series in the capitol building. In December, Webster reported back to Washington that he had succeeded in registering his books for copyright in Virginia, adding, “For this success I acknowledge myself indebted . . . to your politeness.” During this legislative session, as Webster later recorded in his memoir, Virginia’s delegates issued an invitation to all the other states to meet in Annapolis to “form some plan for investing Congress with the regulation and taxation of commerce.” The Annapolis Convention the following September, which consisted of twelve delegates from five states, was the forerunner to the Constitutional Convention. As an elder statesman, Webster took fierce pride in recalling even his tangential connections with such seminal events in America’s founding.

Having completed his business in Richmond, Webster crisscrossed the state, moving on to Petersburg, Williamsburg and Alexandria. The layout of Virginia’s principal towns, which placed theaters rather than churches at the center, left him dismayed. He described Petersburg as an “unhealthy place” with some three hundred houses, the same number as in Richmond. Only Williamsburg appeared tolerable. As he wrote in his diary, the former state capital, though decaying, “consists of 230 houses well built and regular.” But a small turnout for his readings at the “large and elegant” College of William and Mary soured him on all the state’s inhabitants. On December 7, he observed, “Read my second lecture to the same number. . . . the Virginians have little money & great pride, contempt of Northern men & great fondness for dissipated life. They do not understand grammar.” In an effort to combat sagging attendance, Webster dashed off reviews of his own lectures. In an “Extract of a letter from a Gentleman in Virginia to a friend in this town,” which appeared in Baltimore’s Maryland Journal on January 3, 1786, an “anonymous” reporter noted, “Mr. Webster has paid us a visit—his lectures in support of his plan were delivered and much approved by the first characters . . . I think it is high time to dispossess ourselves of prejudice in favour of Britain so far as to act ourselves.”

On January 20, a lame Webster—he had hurt his leg when his horse slipped on an icy road—was back in Baltimore, catching up on his correspondence. Since the New Year, he had lectured in both Annapolis and Frederick as he attempted to curry favor with Maryland legislators. Webster took a liking to Annapolis, whose 260 houses he considered “more elegant . . . in proportion than in any town in America.” Maryland’s state capital also offered ample opportunities for dancing with “a brilliant circle of ladies.” On January 11, his last night in town, Webster noted in his diary, “Visit the ladies; tell them pretty stories.”

After a week of meetings and lectures in Frederick, Webster had reached Baltimore on the nineteenth. The following day, he explained the purpose of his trip to Timothy Pickering, who had introduced himself to Webster a few months earlier in a letter praising his Grammatical Institute. To the recently retired quartermaster general, whom he was looking forward to meeting soon in Philadelphia, Webster wrote, “I shall make one general effort to deliver literature and my countrymen from the errors that fashion and ignorance are palming upon Englishmen.” For Webster, his personal quest to sell more books was synonymous with the heroic effort to rescue America and its language from the clutches of the fashion-loving, theater-addicted British. Though this stance was self-serving, it also had a ring of truth. By 1786, America’s union was in a state of disarray. As David Ramsay, the South Carolina delegate who was the acting president of the Continental Congress, put it that February, “There is a languor in the states that forbodes ruin. . . . In 1775 there was more patriotism in a village than is now in the 13 states.” His language reforms, Webster sensed, could be instrumental in restoring national pride.

However, the usually confident Webster wasn’t convinced that he could pull off this daunting feat. Aware that he lacked the charisma of more dynamic speakers such as Moyes, who attracted as many as a thousand listeners to his talks, he confided his fears to Pickering: “Two circumstances will operate against me. I am not a foreigner; I am a New Englandman. A foreigner ushered in with titles and letters, with half my abilities, would have the whole city in his train.” But Webster’s cri de coeur to Pickering had little to do with the precise nature of the challenge he faced. A foreigner could never have succeeded in his mission, which was to reshape America’s language. In fact, now that Webster had left the South, his distinguished New England pedigree was bound to open doors. Yet Webster tended to see himself as a beleaguered outsider even when he was a respected insider.

Before heading to the big stage of Philadelphia, then America’s largest city with some forty-five hundred houses (as he himself would soon determine), Webster stopped off in Delaware. Unfortunately, he arrived in Dover just as the legislature was ending its session. However, his visit to the capital would not be in vain, as a committee was appointed to look into a copyright law, and a bill was passed during the next session. Webster was greatly relieved to be out of the South, which he would never visit again. Of the response to his lectures in the four-hundred-house town of Wilmington, he observed, “More taste for science in these states than below.” In Wilmington, Webster also hobnobbed with John Dickinson, who had just finished a term as governor of both Delaware and Pennsylvania, and would later represent Delaware at the Constitutional Convention. Using his favorite encomium, in his diary Webster described the so-called Penman of the Revolution—before the war, Dickinson had authored the influential essay “Letters from a Farmer in Pennsylvania”—as “a very sensible man.”

Webster’s month in Philadelphia was memorable. On February 15, his second night in town, he enjoyed the first of several dinners with Pickering, whom he characterized as “one of the best of men.” The following evening, from his perch at Mrs. Ford’s lodging house on Walnut Street, he wrote a letter, introducing himself to Benjamin Franklin:

Mr. Webster presents his respects to his Excellency President Franklin and begs him to peruse the enclosed papers and correct any mistake in the principles. It is designed to collect some American pieces upon the discovery, history, war, geography, economy, commerce, government, &c. of this country and add them to the third part of the Institute, in order to call the minds of our youth from ancient fables and modern foreign events, and fix them upon objects immediately interesting in this country. A selection for this purpose should be judicious, and the compiler feels his need of assistance in the undertaking. He will do himself the honor to call in a few days and take the advice of his Excellency.

This consummate compiler didn’t actually need Franklin’s help in putting together a new edition of his reader. But having won over America’s most influential citizen a year earlier over dinner in Mount Vernon, Webster was now eager to move on to number two. While he lacked the social skills necessary to form intimate friendships, he was adept at ingratiating himself with the powerful. Flattery he knew. And Franklin, who, as the newly elected president of Pennsylvania, also headed the board of trustees of the University of Pennsylvania, quickly grew fond of Webster. As a fellow polymath who was also obsessed with education, Franklin, then eighty, would anoint Webster his intellectual heir. For the remaining four years of his life, Franklin would prove to be Webster’s steadfast colleague.

The day after composing his note, Webster met Franklin for the first time. The elder statesman immediately gave Webster permission to use a room in the university for his lectures. Franklin also talked about one of his pet projects, his plan for spelling reform. For years, the former printer and publisher, who had recently returned from France, had been interested in establishing a new English alphabet based on phonetic principles. Webster, too, was intrigued by aligning spelling more closely with pronunciation. Under a purely phonetic system, Webster would later note in his diary, “every man, woman and child, who knows his alphabet, can spell words . . . without ever seeing them.”

Shortly after those initial meetings with Franklin, Webster reported back to George Washington: “I am encouraged by the prospect of rendering my country some service, to proceed in my design of refining the language and improving our general system of education. Dr. Franklin has extended my views to a very simple plan of reducing the language to perfect regularity. Should I ever attempt it, I have no doubt that I should be patronized by many distinguished characters.”

Webster was thrilled by the possibility of collaborating with Franklin. He hoped thereby both to serve his country and to improve his chances of finding more support (“patrons”) for his own work. Webster was keenly aware of what the ability to drop such big names as both Washington and Franklin could mean for his future. On May 24, after he had left Philadelphia for New York, he shared with Franklin some thoughts on the latter’s proposed orthographic changes, noting that Washington was likely to be supportive of their efforts. “Could he be,” Webster stressed, “acquainted with the new alphabet proposed, [the General] would undoubtedly commence its advocate.” In a postscript to this letter, Webster asked Franklin to endorse his Grammatical Institute. By the summer of 1786, Webster and Franklin were making plans to confer on spelling reform in Philadelphia in the fall.

Webster’s trip to Philadelphia in early 1786 proved fruitful in other ways as well. Shortly after his arrival, he enjoyed another round of discussions with both Pelatiah Webster and Dr. Moyes, who was winding up his American tour. Webster also met Dr. Benjamin Rush, a signer of the Declaration of Independence then settling in as a physician at Pennsylvania Hospital. A social activist, Rush hoped to “remake America” by revamping both education and medicine, and he would develop into one of Webster’s favorite correspondents. Though Rush respected Webster’s intelligence, he had some qualms about his character. Rush would enjoy repeating to friends what Webster said to him after he had congratulated him upon his arrival in Philadelphia: “Sir, you may congratulate Philadelphia upon the occasion!”

On February 27, Webster was introduced to Rush’s old friend Thomas Paine, the author of the famous Revolutionary pamphlet, whose title, thanks to Rush, had been changed from Plain Truth to Common Sense. Paine was then soliciting comments on his engineering prowess, as he had just completed a design for a new suspension bridge. Examining Paine’s model, Webster rendered the following verdict in his diary, “Executed, in miniature, with success.”

Webster’s language lectures at university hall on Fourth Street, which he considered “a large clumsy building,” drew consistently good crowds; the hundred and fifty “mostly literary characters” in attendance at his sixth and final lecture on March 11 expressed their approval with “great applause.” But while Webster achieved many of his objectives—he also registered his speller under the state’s new copyright law—his sojourn in Philadelphia was not without disappointment. In late February, he noted in his diary, “Go to the Assembly; the ladies will not dance with strangers if they can avoid it—polite indeed!” Though Webster was running in elite circles, his failure to find dancing partners that night made him feel like a social outcast. “People in high life,” he added, “suppose that they have a right to dispense with the rules of civility.” A month later, after hosting a farewell Sunday dinner for his newfound Philadelphia friends, he was gone.

From Philadelphia, Webster moved on to Princeton, where he stayed at the home of Samuel Stanhope Smith, the president of the College of New Jersey, whom he had first met nearly four years earlier. Discovering that most of the students, then busy preparing for exams, were too impoverished to pay for tickets, Webster nixed his plan to deliver lectures. On March 24, he scurried out of town after just three days. He did have time for a quick house count: The small college town had just ninety. Of this stop, his diary mentions a couple of dinners with Dr. Smith, a tea at the home of the local parson and some scattered data, “48 rooms in College, 70 students, Presidents salary £ 400. Professor of moral philosophy £ 200. Tutors £ 150 currency.”

With anxiety about pounds and pence racing through his mind, Webster began thinking about how to garner some solid gate receipts in the nation’s capital.

UPON ARRIVING IN NEW YORK on Saturday, March 25, Webster found a room at Mrs. Ferrari’s lodging house at 56 Maiden Lane—then a string of small shops and elegant houses. (A few years later, Secretary of State Thomas Jefferson would live at 57 Maiden Lane). He was residing down the street from Aaron Burr and his family, whom he visited on his first day in town, just as he had the year before. On Monday the twenty-seventh, Webster met New York’s mayor, James Duane, who personally procured the use of city hall for his lectures. This was a major coup because the three-story building, located at the corner of Wall and Nassau Street, where Federal Hall now stands, had since 1785 doubled as the halls of Congress. Following in the footsteps of other distinguished guests such as Dr. Moyes, Webster would give his series of six lectures in its second-floor assembly chamber, whose walls were adorned with paintings of Columbus, Washington and France’s King Louis XVI, then America’s closest foreign ally.

Despite some severe snowstorms in early April, Webster maintained an active social schedule. He enjoyed numerous teas and dinners with several national leaders, including Dr. David Ramsay, who presided over Congress during John Hancock’s illness, and the New York delegate Judge Zephaniah Platt, the father of Jonas Platt, the future congressman whom he had taught in Goshen. Webster’s mood was largely buoyant, even when attending the theater. After seeing The Provoked Husband, a Restoration comedy by John Vanbrugh, Webster reported in his diary that the actors performed well. However, he also alluded to some irritation, adding, “Some low scenes and indelicate ideas interspersed here and there are very exceptionable [objectionable]. Every exhibition of vice weakens our aversion for it.” In point of fact, Vanbrugh’s farce, which featured characters such as the simpleton Sir Francis Wronghead, contained nothing racy. But Webster never did take to social satire. A decade later, beneath a newspaper clipping of an eighteenth-century poem, “The Bunter’s Wedding,” which spoofed the dregs of London society, he would pencil in the following comments, “Too low for the sublimity of my genius and the elegant taste of N. Webster.”

On the morning of April 27, at the invitation of Dr. Ramsay, Webster attended a special breakfast in honor of Captain O’Beal, the Seneca Indian chief, who was then negotiating with federal authorities. “The Seneca Chief & five others,” Webster wrote in his diary, “. . . behave with great civility, & took tea and coffee with decency and some appearance of breeding. When they left the house they shook hands with men & women, without any bow, wearing strong marks of native independence and dignity.” Webster, who donated one sixth of the receipts from his New York lectures to the poor, would forever be concerned about the plight of the downtrodden.

That evening, Webster gave his final lecture before an appreciative crowd of two hundred, which included Dr. Ramsay as well as many other congressional delegates.

As Webster awoke on Friday the twenty-eighth, he was filled with pride. His twice-weekly lectures at city hall, in which he had advocated purifying America from “the principles and effects of a modern corruption of language in Great Britain,” had been a resounding success.

Having decided to move on to Albany on Monday, May 1, he had just one final weekend in New York. This was the morning, he decided, when he would begin his count. With his broad hat and walking stick, the impeccably dressed Webster marched out onto Maiden Lane.

The entire city was then confined to today’s financial district, so Webster figured he needed only a day to complete his task. Along the East River, the city ran a total of about two miles; Grand Street was at its northern tip, above which began a highway called “Road to Boston.” Along the Hudson (or North) River stood just a mile of paved roads. From the city’s west bank to its east, the distance was on average three-quarters of a mile; its entire circumference was thus about four miles.

The New York that Webster was about to circumnavigate was still suffering from the aftereffects of the seven-year British occupation, which had ended just two and a half years earlier. The rubbish and detritus from the Great Fire of 1776, which had destroyed some five hundred houses as well as Trinity Church, the city’s first Episcopal church, were still evident. As Webster headed down from Maiden Lane to the Battery, he noticed that many of the brick buildings with tiled roofs could use a coat of fresh paint, and that vacant lots were everywhere. The city wouldn’t get its much-needed face-lift until the following year when its population—about twenty-four thousand at the time of Webster’s walk—would begin to swell. The pavements upon which Webster trod on that spring day were also by and large not yet mended.


This 1789 map was by John McComb, Jr., Manhattan’s most prominent architect, who later designed both Gracie Mansion and The Grange, Alexander Hamilton’s retreat.

Two years later, Webster wrote up what he saw on that spring day. In the March 1788 issue of The American Magazine, a New York literary journal that he began editing in late 1787, Webster published an article, “General Description of New York.” In this twenty-page piece, Webster provided a complete inventory of New York, which was so admired by historians that it was republished a century later as the preface to a facsimile edition of David Franks’ New York Directory for 1786. New York’s first directory, Franks’ eighty-page volume consists primarily of the street addresses of the city’s residents and businesses (e.g., under “Lawyers, Attornies and Notaries Publics &c” are listed about forty names, including “Aaron Burr, Esq., 10 Little Queen Street, and “Alexander Hamilton, Esq., 57 Wall-st.”) While Franks’ lists of individuals provide a micro-level view of New York’s contents, Webster’s prose furnishes the macro-level view.

As Webster examined the houses on Broadway, he basked in the street’s grandeur. As he put it in the 1788 article: “But the most convenient and agreeable part of the city is Broadway. This street runs upon the height of land between the two rivers, beginning at the fort, near the south of the city and extending to the hospital in front of which it opens into an extensive plain or common.” The hospital just north of Chambers Street marked the end of the developed area on New York’s west side. On the fields in front, Webster spotted about two hundred horses and cows that were grazing. Behind the hospital was an out-of-the-way orchard where a week earlier, Webster had witnessed a duel that fatally wounded George Curson, an Englishman accused of seducing a woman from a prominent Old New York family. While Webster also considered Wall Street “elegant,” he lamented that “most of [the other streets] are irregular and narrow.” New York would never appeal to Webster as much as the orderly New Haven and Philadelphia.

As Webster walked, he also paid close attention to New York’s churches, which then constituted its skyline. He was impressed by the neatness of its Protestant edifices—namely, the three Dutch, three Episcopal and four Presbyterian churches. In his article, he included detailed descriptions of all ten, which highlight their precise dimensions. “The Third Presbyterian Church,” he remarked, “was erected in the year 1768, is a genteel stone building, sixty-five and a half feet long and fifty-five and a half feet wide; and stands in Little Queen-street.” Of the city’s other churches, his article would note just his count:

German Lutheran 2 

Roman Catholic 1 

Friends’ Meeting 1 

Anabaptists 1 

Moravians 1 

Jews Synagogue 1

Webster completed his tallying by the early evening, leaving him enough time to have tea with Peter Vandervoort, the sheriff of Kings County.

That night, Webster wrote in his diary, “Take the number of houses—3500 nearly.” In his 1788 article, in which he included his house count data from across the country along with a host of other demographic information about the city, he would publish an exact figure: 3,340.

In his published account of New York, Webster would also supplement his raw data with some general comments about its citizens. Webster cited William Smith’s 1757 History of the Province of New York, which carried the following assessment: “The people, both in town and country, are sober, industrious, and hospitable, though intent on gain.” While noting that many changes had taken place since the Revolution, Webster concurred: “Notwithstanding, in point of sociability and hospitality, New York is hardly exceeded by any town in the United States.” Webster remarked how in New York, the members of the principal families mingle freely with other well-bred citizens. He contrasted this warmth, which he himself had experienced, to the “affectation of superiority” that governs the behavior of the leading families in Philadelphia. Webster attributed this difference to the manners of each town’s prevailing sect; while America’s largest city took after the reserved Quakers, its capital adopted the personality of the neat and parsimonious Dutch.

Webster’s 1788 urban portrait would forever define Manhattan during the early days of the Republic.

WHILE WEBSTER WOULD ALWAYS ENJOY keeping track of facts and figures, a chance meeting the following year would reduce his reliance on this particular means to manage his anxiety. Falling in love would bring to an end his days as an aimless wanderer.

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