Winslow was originally an Indian settlement named Taconock. During King William's War, Major Benjamin Church led his third expedition east from Boston in 1692. During this expedition he and 450 troops raided the native villages at both Penobscot (Castine, Maine) and present-day Winslow.

Winslow was then settled by colonists from Plymouth Colony. The area was covered by the land patent given by the English Crown to Pilgrim governor William Bradford and his associates. The earliest settlers had such Old Colony and Pilgrim names as Winslow, Bradford, Warren, and Otis. Descendants of those early settlers can still be found in the town.

In 1754, Fort Halifax was built by order of the Massachusetts General Court on the peninsula at the confluence of the Sebasticook and Kennebec rivers. A settlement subsequently sprang up under its protection, and was named in honor of General John Winslow, of Marshfield, Massachusetts who had overseen the fort's construction. General Winslow was a descendant of Edward Winslow, a Pilgrim governor of Plymouth Colony who arrived on the Mayflower and founded the town of Marshfield. General Winslow lived in the mansion built in 1699 by his father, Isaac Winslow. The historic Winslow House still stands today in Marshfield and is on the National Register of Historic Places.

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