Freeport Harbor is located in Cumberland County, Maine. Part of the Portland metropolitan area, Freeport Harbor is just over 12 nautical miles (21 kilometers or 13 miles) northeast of the Port of Portland. Freeport Harbor is also about 33 nautical miles (38 kilometers or 24 miles) west of Boothbay Harbor.
Before Europeans arrived at the future Freeport Harbor, the indigenous Pennacook people inhabited territory in what is now Massachusetts and southern Maine. Some 30 villages supported about 12 thousand people. However, in 1620, just before English settlers began to arrive in numbers, epidemics had already decimated the population.
After the English were established in Freeport Harbor, several epidemics followed. In 1631, smallpox spread across New England. It came again in 1639. In 1647, influenza swept through the Pennacook territory. Smallpox returned in 1649, and then diphtheria struck in 1659. By 1675, only about 2500 Pennacook survived.
By 1726, the last Pennacook group lived near Concord in New Hampshire. They soon disappeared as a separate people. Today descendants of the Pennacook survive in the Abenaki Nation and among the St. Francois (Abenaki) Indians in Canada.
The town of Freeport Harbor was originally part of North Yarmouth, about seven kilometers (4.3 miles) to the west. Freeport Harbor was incorporated in 1789. Freeport Harbor contained four villages that are now part of the Harraseeket Historic District: Mast Landing, Freeport Corner, South Freeport, and Porter's Landing.
Freeport Harbor's Mast Landing was an important source for timber, much of which was used for masts. Having dammed the Harraseeket River estuary, Freeport Harbor had water power for a sawmill, a gristmill, and a fulling mill. At Porter's Landing in Freeport Harbor, ship-building was important in the years after the American Revolution, reaching its peak in the 1850s.
The biggest of Freeport Harbor's waterfront villages, South Freeport had four shipyards in its heyday. It also supported farming, canning, and fishing. When the railroad arrived in 1849, Freeport Harbor's South Freeport grew as a commercial center. Local piece workers made clothing from fabrics brought to Freeport Harbor from Boston and New York. South Freeport also had a sawmill, a shoe factory, a brickyard, and a granite quarry, all established by local businessman E.B. Mallet.
In 1912, businessman Leon Leonwood Bean opened a store selling the "Bean Boot" in his brother's apparel shop basement. His store in Freeport Harbor was so popular that, starting in 1951, it stayed open 24 hours a day. Adding retail markets and mail order services, L.L. Bean grew to become the most important business and employer in Freeport Harbor.