The History of Portland, Maine, begins when Native Americans originally called the Portland peninsula Məkíhkanək meaning "At the fish hook" in Penobscot and Machigonne (meaning "Great Neck") in Algonquian. The peninsula and surrounding areas were home to members of the Algonquian-speaking Aucocisco branch of the Eastern Abenaki tribe, who died largely due to the introduction of foreign illnesses during colonization. Some were forcibly relocated to current day New Hampshire and Canada during European settlement.

Native Americans There is evidence of Native American presence in what is now called Maine as early as 11,000 BCE. At the time of European contact in the sixteenth century, Algonquian speaking people inhabited present-day Portland. French explorer Samuel de Champlain identified these people as the "Almouchiquois," a polity stretching from the Androscoggin River to Cape Ann and culturally distinct from their Wampanoag and Abenaki neighbors. According to Captain John Smith in 1614, a semi-autonomous band called the “Aucocisco” inhabited "the bottome of a large deepe Bay, full of many great Iles." This bay would later come to be known as Casco Bay, and include the future site of Portland.Bruce J. Borque, Twelve Thousand Years: American Indians in Maine (Lincoln: University of Nebraska Press, 2002), 16; Emerson W. Baker, “Finding the Almouchiquois: Native American Families, Territories, and Land Sales in Southern Maine,” Ethnohistory 51, no. 1 (Winter 2004): 73-100; John Smith, A Description of New England (1616): An Online Electronic Text Edition, Paul Royster, ed., 36.

A combination of warfare and disease decimated Native peoples in the years preceding English colonization, creating a "shatter zone" of devastation and political instability in what would become southern Maine. The introduction of European goods in the 1500s disrupted long-standing Native trade relationships in the northeast. Starting around 1607, Micmacs began raiding their southern neighbors from the Gulf of Maine to Massachusetts in an effort to corner the lucrative fur trade and monopolize access to European goods. The arrival of foreign pathogens only served to compound the violence in the region. A particularly notorious pandemic between 1614 and 1620 ravaged the population of coastal New England with mortality rates at upwards of 90 percent. In this chaotic milieu, groups like the Almouchiquois disappear from the historical record, as they were likely displaced or incorporated into other tribes. However, larger Native communities maintained a presence in the Casco Bay area until King George's War in the 1740s. French military defeat and increasing English settler migration to the area from primarily southern New England impelled most Native Americans to migrate toward the protection of New France, or further up the coast where they remain today.Christopher Levett, A Voyage into New England: Begun in 1623, and Ended in 1624 (London, 1628); Neal Salisbury, °Manitou and Providence: Indians, Europeans, and the Making of New England, 1500-1643 (New York, Oxford University Press, 1982), 50-84; David L. Ghere, "The 'Disappearance of the Abenaki in Western Maine: Political Organization and Ethnocentric Assumptions," American Indian Quarterly 17, no. 2 (Spring 1993): 193-207.

European settlement

The first European to attempt settlement was Christopher Levett, an English naval captain who was granted from the King of England in 1623 to found a permanent settlement in Casco Bay. Levett proposed naming it York after York, England, the town of his birth. Levett was a member of the Plymouth Council for New England and an agent for Sir Ferdinando Gorges, Lord Proprietor of Maine. Levett sailed from England to arrive on the Isles of Shoals in October, 1623. He then spent a month with David Thompson at Piscataqua where he assembled men who had arrived earlier to survey the Gulf of Maine for a suitable site to build a trading house. Levett left some of these men at Casco when he returned to England in midsummer 1624. He wrote a book about his voyage, hoping to generate support for the settlement. But his efforts yielded little interest, and Levett never returned to Maine. He did sail to Massachusetts Bay Colony in 1630 to confer with Governor John Winthrop, but died during return passage to England. It's unknown what became of the men he left behind at Machigonne. Fort Levett, built in 1894 on Cushing Island in Portland Harbor, is named for him.

The next (and first permanent) settlement came in 1633 when George Cleeve and Richard Tucker established a fishing and trading village. The town was then renamed Casco. In 1658, the Massachusetts Bay Colony took control of the area, changing its name again, this time to Falmouth after Falmouth, England, the site of an important Parliamentary victory in the English Civil War. An obelisk monument at the end of Congress Street, where it meets the Eastern Promenade, commemorates the four historical names of Portland.

Raid on Portland (1676) In 1676, the village was completely destroyed by the Abenaki people during King Philip's War. When English colonists returned in 1678, they erected Fort Loyal on India Street to ward off future attacks.

Battle of Falmouth (1690)

The village was again destroyed in 1690 during King William's War by a combined force of 400-500 French and Indians in the Battle of Falmouth. Portland's peninsula was deserted for more than ten years after the attack. Massachusetts built another fort to the north of the Presumpscot River in present-day Falmouth called Fort New Casco in 1698. Fort New Casco was successfully defended during the Northeast Coast Campaign (1703) of Queen Anne's War. Fort Loyal at the base of India Street was used throughout King George's War and then repaired during the French and Indian War in 1755.

American Revolution On October 18, 1775, the community was destroyed yet again, bombarded for 9 hours during the Revolutionary War by the Royal Navy's HMS Canceaux under command of Lieutenant Henry Mowat.Louis Arthur Norton, "Henry Mowat: Miscreant of the Maine Coast," Maine History, March 2007, Vol. 43 Issue 1, pp 1-20, The Burning of Falmouth left three-quarters of the town in ashes—and its citizens committed to independence. When rebuilt, the community's center shifted from India Street to where the Old Port district is today.James L. Nelson, "Burning Falmouth," MHQ: Quarterly Journal of Military History, Autumn 2009, Vol. 22 Issue 1, pp 62-69

Trade and shipping center

Following the war, a section of Falmouth called The Neck developed as a commercial port and began to grow rapidly as a shipping center. In 1786, the citizens of Falmouth formed a separate town in Falmouth Neck and named it Portland. Portland's economy was greatly stressed by the Embargo Act of 1807 (prohibition of trade with the British), which ended in 1809, and the War of 1812, which ended in 1815. In 1820, Maine became a state and Portland was selected as its capital. Reuben Ruby and other free African Americans founded the Abyssinian Meeting House in 1828 on Newbury Street in the East End. In 1832, the capital was moved to Augusta.

In 1851, Maine led the nation by passing the first state law to prohibit the sale of alcohol except for "medicinal, mechanical or manufacturing purposes." The law subsequently became known as the Maine law as 18 states quickly followed Maine. Portland was a center for protests against the law, and the protests culminated on June 2, 1855, in the Portland Rum Riot. Between 1,000 and 3,000 people opposed to the law gathered because Neal S. Dow, the mayor of Portland and a Maine Temperance Society leader, had authorized a shipment of $1,600 of "medicinal and mechanical alcohol." The protesters believed, falsely, that this shipment was for private use. When the protesters failed to disperse, Dow ordered the militia to fire. One man was killed and seven were wounded. Following the outcome of the Portland Rum Riot, the Maine law was repealed in 1856.

The Cumberland and Oxford Canal extended waterborne commerce from Portland harbor to Sebago Lake and Long Lake in 1832. Portland became the primary ice-free winter seaport for Canadian exports upon completion of the Grand Trunk Railway to Montreal in 1853. The city's major passenger rail terminal, Union Station, was opened in 1888. In the 19th century, The Portland Company manufactured more than 600 steam locomotives. Portland became a 20th-century rail hub as five additional rail lines merged into Portland Terminal Company in 1911. Canadian export traffic was diverted from Portland to Halifax, Nova Scotia following nationalization of the Grand Trunk system in 1923; and 20th-century icebreakers later enabled ships to reach Montreal throughout the winter.

In 1880, the Portland Longshoremans Benevolent Society was formed. A primarily Irish and Irish-American trade union, it organized between 400 and nearly 1,400 dockworkers for higher wages and went on short strikes in 1911 and 1913. Membership peaked in 1919 as a result of World War I and Europe's need for Canadian grain.

Regional cosmopolitan capital

Portland's period of greatest cosmopolitan prominence was in the first four decades of the nineteenth century, when the city was "a rival, and not a satellite of either Boston or New York." In that period, Henry Wadsworth Longfellow got his start as a young poet and John Neal held a central position in leading American literature toward its great renaissance, having founded Maine's first literary periodical, The Yankee, in 1828. Other notable literary or artistic figures who got their start or were at their prime in that period include Grenville Mellen, Nathaniel Parker Willis, Seba Smith, Elizabeth Oakes Smith, Benjamin Paul Akers, Charles Codman, Franklin Simmons, John Rollin Tilton, and Harrison Bird Brown. By mid-century, Portland also began to rival Rochester, New York, as a center for social reformers.

The Great Fire and rebuilding

The Great Fire of July 4, 1866, ignited during the Independence Day celebration, destroyed most of the commercial buildings in the city, half the churches and hundreds of homes. More than 10,000 people were left homeless. After this fire, Portland was rebuilt with brick and took on a Victorian appearance. Prosperous citizens began building mansions in the city's fashionable West End.

The quality and style of architecture in Portland is in large part due to the succession of well-known 19th-century architects who worked in the city. Alexander Parris (1780–1852) arrived about 1800 and endowed Portland with numerous Federal style buildings, although some were lost in the 1866 fire. Charles A. Alexander (1822–1882) designed numerous Victorian mansions. Henry Rowe (1810–1870) specialized in Gothic cottages. George M. Harding (1827–1910) designed many of the commercial buildings in the Old Port of Portland, Maine, as well as ornate residential buildings. Around the turn of the century, Frederick A. Tompson (1857–1919) also designed many of city's residential buildings.

But by far the most influential and prolific architects of the West End area were Francis H. Fassett (1823–1908) and John Calvin Stevens (1855–1940). Fassett was commissioned to build the Maine General Hospital Building (now a wing of the Maine Medical Center) and the Williston West Church as well as many other churches, schools, commercial buildings, apartment buildings, private residences, and his own duplex home on Pine Street. From the early 1880s to the 1930s Stevens worked in a wide range of styles from the Queen Anne and Romanesque popular at the beginning of his career, to the Mission Revival Style of the 1920s, but the architect is best known for his pioneering efforts in the Shingle and Colonial Revival styles, examples of which abound in this area.