In a classic Herb Green cartoon, published in 1958 in The Saturday Evening Post, a young middle-class couple – the man conservatively attired in a buttoned-down business suit, the woman dressed tastefully in heels, skirt, coat, and hat – join a bespectacled real estate agent strolling past a train station in the suburban community of “Greenitch,” an obvious pun on Greenwich, Connecticut. The man turns to the real estate agent and asks, “By the way, how’s the commuting from up here?” Around the corner, hidden from view, clutching a briefcase and wearing a bowler, a skeleton sits propped against the wall. The point of the cartoon, of course, was that commuter trains frequently ran late – that it sometimes seemed like a man might starve to death before one happened along.

As the cartoon indicates, the advent of rail transportation and the factories it served affected Connecticut in deep and profound ways. Both promoted industrialization and urbanization, completely transformed the state’s demographic makeup, and caused the growth of its modern commuter culture. Indeed, so significant were the changes brought by the mills and railroads that a good argument can be made for dividing Connecticut’s history into three basic eras: an Age of Farm and Sail (from the 1630s to the 1820s or 1840s), an Age of Industry and Rail (from the 1820s or 1840s to the 1950s), and a postindustrial Automobile Age (from the 1950s to the present).

The Age of Industry and Rail fundamentally altered Connecticut’s demography. The earliest colonists from Europe, arriving during the Age of Farm and Sail in the 1630s and 1640s, had settled chiefly along Long Island Sound and on the banks the big rivers: the Thames below Norwich, the Connecticut below Warehouse Point, and the Housatonic below Derby – all within the reach of ocean-borne sailing ships. As late as 1686 colonists still had not settled in most of the upland areas where the majority of the water-powered industrial mills would later be located. Several factors explain this pattern. Unlike the uplands, the tidewater regions had extensive stretches of salt marsh, which provided abundant hay for the colonists’ cattle. The level terrain of the coastal slope and fertile soil of the river intervales offered better farmland than the steeper, rockier uplands. And unlike the tidewater area, the majority of the hill country remained longer under the control of the native peoples – until after Metacom’s War in 1675-76.

But the key factors were jobs and transportation. Until the Industrial Revolution, not only were most of the farms located near the coast, but so were most of the non-farm jobs in seafaring and fishing. And as for transportation, well, colonial roads were poor quality – unpaved, ungraded, unlabeled, muddy, and usually without bridges. Native trails were even worse. Sailing vessels were the best – and usually only – way to transport goods in bulk. Sailboats were so common that, for most of the colonial period, eastern Long Island was socially and culturally more a part of Connecticut than it was of New York, the two sides of the Sound tightly linked by sail. Throughout the Age of Farm and Sail, the Sound served as Connecticut’s chief “highway,” with the three major, navigable rivers acting as the leading secondary arteries.

It is not surprising, then, that during the Age of Farm and Sail the majority of Connecticut’s population lived near tidewater. According to the federal census of 1800, of the state’s ten most populous towns, only one – Litchfield (4,285) – was located away from tidewater. The other nine – Stonington (5,437), Hartford (5,342), New Haven (5,157), New London (5,150), Norwalk (5,146), Middletown (5,001), Lyme (4,380), Stamford (4,352), and Groton (4,302) – were all within reach of sailing ships.

However, the advent of industrial mills in the 1820s and rail transportation in the 1840s led to a reshuffling of the population and created a more even distribution between the tidewater and the uplands. By 1900 fully half of Connecticut’s twenty-two largest towns were located inland, away from tidewater. True enough, the three largest towns – New Haven (108,027), Hartford (79,850), and Bridgeport (70,996) – were still on the coast or along a major river. But the fourth, fifth, and sixth largest – Waterbury (51,139), Meriden (28,659), and New Britain (28,202) – were all inland, connected to the outside world by rail, not sail. Moreover, in 1900 Connecticut’s four principal rail “hubs” – New Haven, Hartford, Waterbury, and Windham/Willimantic (10,137) – ranked first, second, fourth, and fifteenth among the state’s towns.

To be sure, the railroad was not the only factor contributing to the population shift from the tidewater to the uplands. The waterfalls that drove the factories of the Industrial Revolution were just as significant, if not more so. Yet without the railroads to bring in the heavy, bulky raw materials and carry out the finished manufactured goods, it is difficult to imagine that industrial towns like Waterbury, Meriden, New Britain, Torrington, Ansonia, Windham/Willimantic, Naugatuck, Manchester, Bristol, or Vernon/Rockville would have experienced as much growth as they did. In a famous essay on industrialization and railroads, the distinguished economic historian Robert Fogel once concluded that the Industrial Revolution would have occurred whether railroads had existed or not. But he also concluded that without railroads, industrial production and urban growth would have occurred in different locations – chiefly in areas adjacent to major waterways, which in Connecticut meant tidewater. If Fogel is right, without railroads industrialization in Connecticut would have been confined mostly to towns like Norwich, New Haven, and Derby, which had both waterfalls and access to water transportation. Willimantic would have had a few mills, yes, but probably not the giant Willimantic Linen Company (renamed the American Thread Company in 1898) that at the turn of the century was Connecticut’s biggest factory and the United States’ largest thread mill. Manchester would not have had the mammoth Cheney Brothers silk mill.

However, in another way the coming of the mills and railroads also caused Connecticut’s population to become less evenly distributed than in the Age of Farm and Sail. With industrialization, a major shift occurred, from the old farming and fishing towns of the 1600s and 1700s to the burgeoning new industrial and commercial cities of the 1800s and 1900s. To contrast the two eras, we can divide Connecticut’s towns in both 1800 and 1900 into four broad categories: smaller-than-average towns (those with populations less than 50% of the annual mean), average-sized towns (those with populations between 50% and 150% of the mean), larger-than-average towns (those with populations between 150% and 250% of the mean), and much-larger-than-average towns (those with populations in excess of 250% of the mean).

In 1800, near the end of the Age of Farm and Sail, Connecticut had 250,902 residents distributed among 107 towns, for a mean population of 2,345 people per town. Eighty towns (75%) fell in the average category, while only thirteen (12%) were categorized as smaller-than-average, fourteen (13%) as larger-than-average, and none as much-larger-than average. The vast majority of Connecticutters thus lived in average-sized towns with populations between 1,173 and 3,518 – a remarkably even population distribution.

But by 1900, during the Age of Industry and Rail, the situation had changed. Connecticut’s population had risen to 908,420, and the number of towns had increased to 168, with a mean population of 5,407 inhabitants per town. While in the Age of Farm and Sail most towns had been average-sized, in 1900 the majority of towns were in the smaller-than-average category. Of course, an average-sized town was larger in 1900, because the population had increased faster than the rate at which new towns had been added. But in measuring the evenness of population distribution, it is the deviation from the mean that counts. In 1900, 102 towns (61%) fell into the smaller-than-average category, only 43 (26%) fell into the average category, eleven (7%) were in the larger-than-average category, and twelve (7%) were in the much-larger-than-average category. This was because the much-larger-than-average towns, although small in number, were so big in size – so much above average – that they skewed the mean. In 1900 about two-thirds (64%, or 577,497) of Connecticutters lived in the state’s twenty-two largest towns. Population was no longer even close to being distributed evenly.

The urban historian Kenneth Jackson explains why. Most of the jobs were now located not on the farm or dockside, as they had been in the Age of Farm and Sail, but in the factories and shops of the growing industrial and commercial cities. Because riding the rails was expensive, most people could afford to live no more than a mile or two from their urban workplaces. Although trains and trolleys allowed most middle- and upper-class people to live in the suburbs and ride to work, most of the factory workers, shop clerks, and laborers – earning less than $600 a year – had little choice but to hoof it. According to Jackson, wealthy people typically took the trains, middle-class folks generally rode the trolleys, and working class people usually walked. As a result, population clustered around the largest cities.

Not only were such cities much larger in the Age of Industry and Rail than they had been in the Age of Farm and Sail, they were also structured differently. In truth, Connecticut did not yet have true cities in 1800. Stonington, Hartford, and New Haven were really no more than large towns. But the urban centers it did have were arranged as traditional “walking cities,” so-called because it was no more than an hour’s walk (about three miles) from the downtown to the outskirts. Because most people preferred not to walk any farther than they had to, the wealthy (and, of course, their live-in servants) gobbled up the highly desired sites downtown, where property values were highest, but the walk to work was also the shortest. The middling sort resided just beyond them, along the quiet side streets. Poor folks inhabited the outskirts, where the property values were the lowest, but the walk to work was also the longest.

In the Age of Industry and Rail the old walking cities disappeared, giving way to what Bruce Stave, a retired professor of urban history at the University of Connecticut, calls “doughnut cities.” The new, modern city centers – industrialized, congested, noisy, dirty, polluted, disease-ridden, and crime-infested – became undesirable as residential spaces and thus mostly uninhabited. They were the “holes” in the “doughnuts.” The poorly paid working classes lived in crowded low-rent districts immediately adjacent to the downtowns, where they could walk to work but also had to endure much of the downtowns’ congestion, crime, and pollution. The middle class inhabited a ring of more-or-less comfortable suburbs lying just beyond the low-rent districts, typically on “the other side of the tracks,” from which they commuted via the crowded, noisy trolleys. One historian calls these middle-class areas “streetcar suburbs.” The affluent upper class lived even further out, in clean, quiet, spacious neighborhoods located on the far edges of the city, from which they commuted in the roomier, more comfortable trains. Industrial growth had made these new doughnut cities necessary. But it was mass transit – trains and trolleys – that made them possible.

Railroads also contributed to Connecticut’s rapid population growth after 1800 – fourfold increases 1800-1900 and 1900-2000. It did so in two ways. First, as we have seen, they encouraged industrialization and commercialization, which created the jobs that attracted and held the newer, larger populations. Second, they also permitted upper- and middle-class workers to hold good-paying jobs in New York City but live in suburban Connecticut.

For such commuters, the question “How’s the commuting from up here?” was more than mere small talk. It touched upon a vital part of their lives. Commuting was not always a pleasant experience. The trains were expensive and frequently late. The locals made too many stops, and the trip was too long. The cars were crowded, the seats often dirty, the air frequently foul, the engines noisy. Yet for many upper- and middle-class Connecticutters, the train ride at the end of the day was the way out and the way home, the means to combine a good job in the congested city with a comfortable house in the peaceful suburbs, the gleaming steel road that connected them to the American Dream.