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The Persistence Of Portland

June 2024
13min read

Small, handsome, and often beleaguered this surprisingly cosmopolitan Maine city has had a history of clawing its wav baclk from oblivion—and today,it’s on an upswing again

I moved to Portland four years ago for a simple reason: After years of living and working in New York City, I was suddenly tired of the incessant noise. Portland seemed to offer me, a nature-loving city person, the best of both worlds. It has the ocean at its doorstep and forests, lakes, mountains, and rolling farmland in its back yard. It’s a city made for walking, with residential neighborhoods downtown. Portland is still small enough that people nod hello on the street, yet its residents come from all over the world.


I moved to Portland four years ago for a simple reason: After years of living and working in New York City, I was suddenly tired of the incessant noise. Portland seemed to offer me, a nature-loving city person, the best of both worlds. It has the ocean at its doorstep and forests, lakes, mountains, and rolling farmland in its back yard. It’s a city made for walking, with residential neighborhoods downtown. Portland is still small enough that people nod hello on the street, yet its residents come from all over the world. And, for the most part, Portlanders, even those from “away,” seem to possess that most attractive of Yankee values, a can-do attitude that takes advantage of good times and perseveres in bad.

From its beginnings Portland has been defined by the sea. When I want to show visitors what makes the city tick, I take them first to the ocean, across the new Casco Bay Bridge and southeast to Cape Elizabeth. At the Portland Head Light, just fifteen minutes from the city center, Atlantic rollers crash against the rocks, raising a drenching spray when the winds and tide are right. If you could sail a boat due east on this same latitude, your next landfall would be the French coast just north of Biarritz, a connection I like to keep in mind in winter, when Maine can seem—well, a bit lacking in joie de vivre . Standing here on the southern cusp of Casco Bay, you can easily imagine why early European explorers sought shelter among its protected shores. Eventually they would make their way westward along the shore until they were staring at the three-mile-long Portland peninsula. Soon they’d have found access inland via a wide river on the south, the Fore, one to the north, the Presumpscot, and a large protected bay, the Back Cove.

Peaks Island, Portland’s busiest and most populous offshore locale, was settled in 1636.

For centuries Indians used the islands and inlets of Casco Bay as hunting and planting grounds. And it was Native Americans who inadvertently inspired Englishmen to exploit the bay’s abundant natural resources. In 1605 Capt. George Waymouth, returning to Plymouth, England, from the Maine coast, brought with him not only the story of his discoveries but also five Indians he had tricked into boarding his ship. He gave three of them to Sir Ferdinando Gorges, military commander of England’s western defenses at Plymouth, who kept them for three years. (What did they make of him? I wonder. And of England?) “The longer I conversed with them,” Gorges later wrote, “the better hope they gave me of those parts where they did inhabit as proper for our uses, especially when I found what goodly rivers, stately islands, and safe harbors those parts abounded with. ... As for the coldness of the clime,” he added confidently, “I had too much experience in the world to be frighted with such a blast.”

Though Gorges never made it to America, he financed some who did. He also persuaded the Crown to give monopoly fishing rights to the Council of New England and obtained for himself and Capt. John Mason a royal grant to the “province of Maine,” designated as all lands between the Merrimack and Sagadahoc Rivers. Many liberal-minded Englishmen in the House of Commons, as well as fishermen from the western seaports, were outraged at the idea of a monopoly on any part of the sea. Adventurous English entrepreneurs continued to make unauthorized trips to the Maine coast, loading up on fish and lumber and furs and occasionally setting up semipermanent trading posts.

One of these was George Cleeve of Plymouth, who with his family and his partner, Richard Tucker, settled on Cape Elizabeth near the Spurwink River, only to be run off by a rival trader in 1632, whereupon they put all their belongings in a boat and sailed around the cape to the eastern end of the Portland peninsula. There, at the point where Portland’s Fore Street begins its ascent up Munjoy Hill, they built the peninsula’s first house and set about farming and trading. A few years later Cleeve got title from Gorges to the whole peninsula and its offshore islands, and with the stroke of a pen he became the nascent city’s most prominent citizen.

Following Fore Street today up the hill to the Eastern Promenade, you’ll find the town’s best view of the bay and the islands, plus an obelisk that honors the first white settlers and notes the names by which the city has successively been known: Machigonne, Casco, Falmouth, and finally Portland. Offshore to the east you’ll see a circular island fort built to defend the harbor in the nineteenth century and named for Gorges. Beyond it lies Peaks Island, Portland’s busiest and most populous offshore locale, first settled in 1636 by the Cleeves’ daughter Elizabeth and her husband, Michael Mitton, and today the home of a thousand residents year round and some fifty-five hundred in summer.

While the early English settlers fished, farmed, cut trees, milled lumber, and appropriated the land, the Indians who had initially helped them became more and more disgruntled. Eventually, incited first by their own leaders and later by the French, they fought back, and murderous Indian attacks became a sporadic but horrifying reality for settlers over the next hundred years, until the capture of Quebec in 1759 broke the power of the French.

The first destruction of Portland’s scattered settlements came in 1676 as an extension of the uprising to the south known as King Philip’s War, and the second occurred in 1690, when the French and Indians laid siege to Fort Loyall at what is now the intersection of Fore and India Streets. William Willis, Portland’s leading historian in the nineteenth century, lamented that almost all records from the seventeenth century were destroyed. After 1690, Willis wrote, the whole territory, “which before the war was covered with an active and enterprising population, was a perfect blank, a thoroughfare for the savage and a resort for beasts of prey.”

After the Treaty of Utrecht between Britain and France in 1713, settlers began to return again, and by 1717 there were enough old and new proprietors on the peninsula and in the surrounding territory for them to petition Massachusetts to incorporate it as the town of Falmonth. Falmouth had an excellent harbor, many mills, and a still-plentiful supply of lumber, but it needed much in the way of agricultural and other goods from the colonies to the south. The Royal Navy and British merchant marine had already discovered Maine’s “great sticks,” the largest and straightest white pines, which were reserved for the king’s use as ship masts.

Today the best place to get a feel for the eighteenth-century settlement is in the Stroudwater section, close to the Portland International Jetport, where waters from the Stroudwater pour into the placid Fore River. In the 1720s Col. Thomas Westbrook and his family saw this confluence as the perfect place to farm and carry on their other businesses, which included a sawmill in Stroudwater Falls, a small mast landing on the Fore, and later, Maine’s first paper mill. The Westbrooks’ house does not survive today, but several other well-tended eighteenth- and early-nineteenth-century houses line Westbrook Street, including the Tate House, built circa 1755 for George Tate and his family. As mast agent, Tate oversaw every step of a lucrative operation. Woodsmen felled huge trees, weighing as much as eighteen tons, and delivered them during the winter by ox-drawn sleds to Stroudwater, where they were rafted down the Fore to the deeper harbor. There they were sorted, trimmed, loaded onto specially built mast ships, and escorted by the Royal Navy to England’s western ports.

The Georgian Tate House, the only pre-Revolutionary structure in Greater Portland open to the public, is well worth a visit. It may look simple to our eyes, but it represented considerable comfort for its time and place, with two front rooms, a spacious hearth room in the back, and four upstairs bedchambers, all with glass windows, a luxury then. Today the house is furnished with period antiques and such reminders of daily life as cast-iron pots and tongs, paddles to beat the straw beds into shape, and children’s cards and games. A strange tragedy haunts the place. In 1770 thieves broke into the storeroom (now the gift shop), and Mary Tate, then sixty, is supposed to have asked her son, William, to prevent a recurrence. He rigged a trip line to a handgun, and either his mother didn’t know about the trap or she forgot, but on September 30 she opened the storeroom door and was shot to death. Although William admitted setting the gun and was found guilty in 1772 of “feloniously killing and slaying one Mary Tate,” he was granted a King’s Pardon later that year.

Back at the harbor, houses and business establishments were springing up, concentrated on lots close to the water and eventually climbing the hill toward Back (now Congress) Street. In 1727 the Harvard-educated Thomas Smith was ordained as the city’s first permanent preacher and recorded in his diary on his arrival in 1725 that there were about fifty-six families in Falmouth, among them “some very good” men, some “mean animals.” Sea trade was Falmouth’s lifeblood. Ships took lumber to England and brought back such necessities as cloth and pots and scissors. Staves for barrels and salted fish went to the West Indies, and sugar and rum returned. Merchants would build a ship, fill its brand-new hold with fish and lumber, and at its destination sell both vessel and cargo.

Unfortunately nothing is left of this vital eighteenth-century port, for the town met its third apocalypse in 1775. That was the year of Lexington and Concord and Bunker Hill, and Maine seethed with resentment against George III. In Falmouth a committee of inspection refused entry to supplies for a new mast ship being built by a local royalist. The shipbuilder called on Capt. Henry Mowatt of the Royal Navy to compel delivery. One day when Mowatt was taking a stroll on Munjoy Hill, Brunswick minutemen who were camped there took him captive. Even though he was let go, the incident rankled, and Vice Adm. Samuel Graves, Mowatt’s commander in chief, ordered the captain to teach Falmouth a lesson.

On October 17, 1775, a vengeful Mowatt gave warning “to remove without delay, the human specie out of the said town.” The next morning his ships opened fire with bombs and cannonballs heated red hot. Throughout the day fires raged, destroying 414 of the town’s 500 buildings, including every structure near the water, the new courthouse, the town hall, and the customshouse. Although no one was killed, the bombardment left nearly two thousand people homeless and destitute as winter approached. George Washington termed Falmouth’s devastation “an Outrage exceeding in Barbarity & Cruelty every hostile Act practised among civilized Nations,” and the sufferings of the residents acted as a rallying cry to patriots everywhere.

As it had done in the past and would do again, the town rebuilt itself, and in the 1780s it began to enjoy a prosperity that would continue with only few interruptions through the nineteenth century. As if to symbolize its renewed vigor, the peninsula separated from Falmouth and became Portland on July 4, 1786. That same year Gen. Peleg Wadsworth and his wife, Elizabeth, finished building the new city’s first brick house, now the Wadsworth-Longfellow museum and the oldest structure on the peninsula. Today it is dwarfed and hemmed in by office buildings on Congress Street; back then it sat alone on top of the hill with views to both the harbor and the Back Cove. After the Wadsworths raised ten children there, the house passed to their daughter Zilpah and her husband Stephen Longfellow, parents of eight, including Portland’s most celebrated literary figure, Henry Wadsworth Longfellow.

This was a prosperous time for Portland. During those years—and on into the 1820s and 1830s, the town’s merchants and bankers built many large houses inspired by London’s suburban villas. Among the most elegant are the Hugh McLellan House, on Spring Street, known today as the McLellan-Sweat House and now part of the Portland Museum of Art; the Stephen McLellan House, around the corner at 116 High Street, now home to the Cumberland Club; and the Richard Hunnewell House, on State Street, designed by the celebrated New England architect Alexander Parris.

The Embargo Act of 1807 temporarily ruined the party. With American ships forbidden to leave port, trade plummeted. Banks and insurance companies failed, and several of Portland’s mercantile fortunes withered. Then, in the War of 1812, the British overran eastern Maine. When no assistance was forthcoming from Massachusetts, Mainers decided they’d had enough of their faraway government. In 1819 they drafted Maine’s constitution in the old First Parish church known as Old Jerusalem. (You can visit the church’s replacement today on Congress Street; built in 1826, it is Portland’s oldest surviving house of worship.) The constitution was a progressive document for its time, guaranteeing religious freedom and requiring no property qualifications for either voting or running for office. Statehood came in 1820, and Portland had a fling as state capital until Augusta became the permanent capital twelve years later.

In the early 1800s leading merchants built big houses inspired by London’s suburban villas.

In 1821 Portland opened the state’s first—and the nation’s second—free high school (for boys; girls weren’t admitted until 1850). In many ways the city was setting the pace for progress in northern New England. One of the benefits of foreign trade is familiarity with other lands and peoples and ideas, and while Portland was no Boston or New York, it was surprisingly cosmopolitan and had its share of literati, reformers, educators, and social progressives. I have particular affection for John Neal, who was known in his day as an original and prolific writer (his first novel, published in 1817, had the arresting title Keep Cool ). Neal was also a promoter of the arts, an athlete who started the first gymnasium in Portland (but lost interest when the club refused to admit some African-Americans he had proposed for membership), and a fierce champion of women’s rights.


At mid-century, shipbuilding, shipping, and fishing were still basic to Portland’s economy, and its value as a port had been enhanced by the building of many toll roads, or “turnpikes,” and canals, including the Cumberland and Oxford, which ran fifty miles inland, connecting Portland and Sebago and Long Lakes. The West Indies trade, always immensely profitable, spurred such investments as J. B. Brown’s immense eight-story sugar factory on brand-new Commercial Street- itself a vast project, more than a mile long and a hundred feet wide, built on landfill where once the waves had lapped the shore. But it was the railroad that would spark the major development of the latter half of the century. Thanks to Maine’s most ardent railroad champion, a lawyer named John A. Poor, the city beat out Boston to become Montreal’s winter port, and the Atlantic & St. Lawrence Railroad was built to connect the two cities and link Maine to all of Canada and the western United States. Founded in 1847, Poor’s Portland Company, whose building still stands on Fore Street, manufactured locomotives and boilers for the Atlantic & St. Lawrence, then for railroads all over the United States and Canada.

On the first Independence Day after Maine’s regiments returned home from the Civil War, Portland anticipated a major celebration. “What we wish to call attention to is the beauty of our city,” wrote an editorialist in the Portland Transcript . “No Portlander can at this season walk our streets in the twilight hours without being proud. …” Sadly, July 4, 1866, would be remembered instead as the most destructive in the city’s history. At dusk a fire started at a boatyard on Commercial Street, and a brisk evening breeze fanned the embers and threw sparks onto roofs nearby. The huge J. B. Brown sugar factory and two foundries went up in flames, and fire companies from all over the area could not control the blaze. It leaped from rooftop to rooftop diagonally through the city center to the Back Cove and then up Munjoy Hill, where it finally burned itself out fifteen hours later.


Amazingly only two people died. Yet the damage was devastating: a third of the city destroyed, about fifteen hundred buildings gone, including city hall, the customshouse, eight churches, four schools, three libraries, and every bank, newspaper, and lawyer’s office. Congress appropriated fifty thousand dollars, and the Army sent fifteen hundred tents, which sheltered some 1,650 people for the rest of the summer. Longfellow, visiting Portland a month after the fire, grieved for his old hometown: “Desolation! Desolation! Desolation! It reminds me of Pompeii, the ‘sepult city.’”

Only two years later, however, the scene lay totally transformed. Not for nothing is Portland’s motto Resurgam and its symbol a phoenix. The stylish brick Victorian structures seen along Middle and Exchange Streets, the heart of the downtown business district, sprang up in virtually no time after the fire, as did many other new buildings. Insurance had not covered all the losses, so Portland citizens had to dig deep into their pockets to rebuild and to fund civic improvements, such as the Maine General Hospital on Bramhall Hill (now. with modern additions, the Maine Medical Center) and Lincoln Park, conceived as a protective firebreak, and the city’s first public recreational area.

The fortunes of Portland have always been an up-and-down story. In this century the biggest influence—both positive and negative—has been the automobile, which replaced the horse and carriage and later the extensive trolley system that had taken people everywhere in and out of town. Eventually passenger rail service to Portland died also (although the long-planned revival of service between Boston and Portland seems nearer reality). The growth of suburban housing and shopping malls has meant a population drop, from 77,634 in 1950 to 64,358 in 1990. Yet Portland is still a major player in New England’s economic and cultural life, and in terms of seeing new possibilities for itself, the city has been on an upswing for the past twenty-five years. This began, as most things do, with a shift in spirit.

Like many another American city, Portland had to be shocked into recognition of its architectural heritage. In the 1960s two major granite structures, Union Station, on St. John Street, and the old Post Office, on Middle Street, fell to the wrecker’s ball. Their replacement by a strip mall and a parking lot, respectively, came to symbolize the unthinking tear-it-down mentality of postwar “urban renewal.” An angry and aroused group of citizens, many of them relative newcomers to the city, formed Greater Portland Landmarks to educate the public and spearhead preservation efforts.

In the 1970s a vision for Portland’s historic neighborhoods grew. Instead of featuring rundown, empty warehouses and desolate bars, why couldn’t the Old Port become Portland’s premier business, shopping, and tourist area? Mightn’t professionals like to locate by the water and enjoy high-ceilinged offices with harbor views? Today not only the Old Port but much of Portland is enjoying the fruits of the risks taken by restoration-minded developers two decades ago. Congress Street, lined with empty storefronts only a few years back, has revitalized itself as the Arts District, anchored by the Portland Museum of Art, the Children’s Museum, the Maine College of Art, and a nearly completed community arts center. Homeowners and landlords all over the city have improved the housing stock. New architecture—such as the popular downtown Public Market—blends harmoniously with the old. Residents on the West End and the Eastern Promenade take particular pride in the upkeep of a concentrated treasure of nineteenth-and early-twentieth-century houses. There is some grousing about the strict regulations governing historic properties, but most Portlanders realize that preservation not only raises property values and puts a shine on the city’s face but acts as a catalyst for all kinds of entrepreneurial efforts.

As I make my own way around my new hometown, I’m grateful that Portland honors its past. Walking where so many others have walked, you can readily catch glimpses of how it must have been. These old walls do indeed talk. At the museum in the Wadsworth-Longfellow House, I am in an empty building, but I hear whispers and giggles from the many children who grew up in those dark rooms. Strolling by the grand Federal houses on State and High Streets, I see women in long dresses welcoming visitors into airy candlelit parlors. Wandering the overgrown ruins of Riverton Park, I imagine trolley cars depositing Sunday pleasure-seekers there. Tramping the Eastern Promenade, where once the Indians had their campfires, or stumbling over cobblestones in the Old Port, I feel the many who were here before me, deluding themselves, as I do now, that this is it, this is the way things are, even as everything moves and changes, as future and past partake of every passing moment.


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