The original inhabitants of what we now call Portland belonged to a Native American tribe known as Wangunk ("big bend," referring to the Connecticut River which curves around half the Town's perimeter). They arrived in the area between 8,000 and 10,000 years ago, surviving on local game and their own crops.

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The first European-Americans came to the Portland area in the 1650's, the first being James Stanclift, an English stonecutter. They were drawn by the availability of brownstone, a valuable resource for construction and for gravestones. The close proximity of the river to these brownstone quarries made the transportation of cut stone affordable. This resulted in a number of flourishing family businesses, that eventually consolidated into three major partnerships.

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Portland supplied quality brownstone from New York and Boston to San Francisco, and employed over 1,500 people during the 1850's. More than 25 ships transported the stone to major population centers in the United States, Canada and even England.

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Many local businesses were tied into the quarry-works industry. Shipbuilding, transportation, animal husbandry (caring for oxen and horses used in the quarries), blacksmithing and mill -work. As the industry grew, so did the local community, and with it all the businesses one might expect: retailing, construction, farming, medicine, and law. Churches were raised, and school houses provided. The increase of wealth resulted in the building of large, comfortable homes. By the 1850's, the economic center of town shifted toward the shipbuilding, Gildersleeve area.

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The quarries' need for labor brought waves of immigrants to Portland. First came the Irish, then the Swedes, followed (to a lesser extent) by Italians, each group adding their distinct contributions to the unique character of the town. Special housing was provided by the quarry owners to shelter these newcomers, who then became the backbone of the town.

Other mines proliferated throughout the area, as the hills and valley of Portland were found to be a geologist's dream. Mica contributed to the war effort in the middle of the twentieth century. Semi-precious stones attracted shovels and picks from across the country.

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Tobacco farming also took hold, covering river-valley fields with shade-netting and migratory workers.

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The market for brownstone fell into decline at the turn of the 20th century. Brownstone could not compete with less expensive and more versatile construction materials, like concrete. In 1936, the river flooded into the quarry sites, effectively ending the brownstone industry. This quickly marked the decline of the shipbuilding industry as well, and the Town of Portland underwent an economic transformation. Residents of Portland found employment elsewhere, and dedicated their community efforts to quality of life. In other words, the cultural focus became more civic- and family-oriented, making Portland an all-around great place to live.

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Today, the scenic quarries, located just off of Main Street in the central business district, are recognized as historically significant, and a potential destination point for educational purposes and heritage tourism.

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The quarries remain as a scenic natural resource, reminiscent of Portland's past. Ship-building has been replaced by marinas. Geological mining sites are now preserved within a beautifully sculpted 18 hole golf course. Surnames of immigrant quarry workers, tobacco farmers, ship-builders and early entrepreneurs still populate the area, living remnants of Portland's history.

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The town was first known as East Middletown, maintaining its ties across the river. It became incorporated as Chatham in 1767, which included what is now known as East Hampton and Middle Haddam. When these three districts gained distinct characters of their own, separation again occurred, each taking their present-day names. The name Portland was borrowed from Portland in the English county of Dorset, which was famous for its quarry industry.