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Like other towns in coastal Maine, Freeport was settled in the 18th century by residents of the southern part of the state--Massachusetts, which it was a part of until 1820. The Harraseeket River provided mill power and transportation, enabling growth and separation from North Yarmouth in 1789. The arrival of the railroad in 1849 led to a late-century economic boom fueled by entrepreneur E.B. Mallet. Piggybacking on the established industrial infrastructure, L.L. Bean and other retailers prospered in the next century, forming the core of activity at the heart of Freeport Village today. South Freeport was sustained by shipbuilding that ebbed and flowed through the 20th century, and largely because of that industry, it remains a historic village to this day. Because of Freeport's rapid growth and a number of downtown fires, historic buildings have been lost, moved, or altered over time, though the historical society has advocated for preservation and maintains a broad collection of photographs that visually record these changes.

Vinalhaven Island has been the home port of a productive commercial fishing fleet for over 200 years. By 1819, Vinalhaven vessels were fishing for cod and herring from Seal Island all the way to Labrador waters. By 1878, Carver's Harbor was lined with docks, fishhouses, a sail loft, a net factory, and the Lane & Libby fish plant. Throughout the 19th century, boats brought bait, salt, and supplies to Vinalhaven and returned with fish and granite from the island's quarries. Lighthouses at Brown's Head, Heron Neck, Saddleback Ledge, Goose Rock, and Matinicus guided mariners through storms. In Vinalhaven shops, boatbuilders constructed small dories, peapods and double-enders, masted schooners, and lobster boats, as well as the 365-ton Margaret M. Ford. Passenger ferries played an important role as the primary link between Vinalhaven and the mainland. The island has long been a successful center of maritime economic activity, so it is no surprise that islanders call it "the center of the universe."

Until hard surface, all-weather thoroughfares were constructed and private automobiles became numerous, residents of York County depended on trolleys for local transportation. Many people commuted regularly to and from work on the electric cars, which also carried children to school from September through June. In the winter, when streets, roads, and highways were buried under deep drifts, powerful snowplows swiftly cleared the street railway tracks after severe storms so the trolleys could get through. Maine's York County boasted more than 100 miles of trolley lines from 1907 through 1922. The World War I years were difficult for street railways throughout the United States. Soon after the conflict ended, automobiles began rolling off the assembly lines at progressively more attractive prices. As the nation entered the "Roaring Twenties," more and more residents of York County acquired motorcars and no longer needed the trolleys that had served them so faithfully through the years. York County Trolleys takes us on a visual journey from Kittery to Old Orchard Beach, from Old Orchard to Portland, and inland to Eliot, South Berwick, and Sanford.