The King's Highway

  1. Location and Background
  2. History
  3. Migrations and Towns
  4. Traveler : John Gyles

  1. History
The first section of the King's Highway was built on the orders of the Massachusetts government in 1653 in order to connect Kittery and York to Boston. The road was soon extended to Portland. Over the next century, the route was expanded, a variety of improvements were made, and it was upgraded to a military road in 1761. The completed King's Highway went along the Gulf of Maine, around Casco Bay, to North Yarmouth, and then overland to Brunswick on the lower Androscoggin River. From Brunswick, a traveler went by boat to Georgetown, on Arrowsic Island - at the mouth of the Kennebec River - then to the area that would become Wiscasset. From this port town, they could continue around Penobscot Bay and along the Gulf of Maine to Machias. Various spur roads also allowed travellers on the King's Highway to go inland.

Plan of roads between Portland, Penobscot Bay, and Hallowell, 1796

(Courtesy of the Commonwealth of Massachusetts Archives, Boston).

For example, by the 1650s, trails and roadways had also been built up the Kennebec River to Merrymeeting Bay and connected to trails to Cushnoc (Augusta). A traveler could also go from Georgetown to the area that would become Dresden, then continue on to Gardiner, Hallowell, Fort Western (Augusta), and Fort Halifax (Winslow), then over the Lake Megantic Route to Canada. The King's Highway also connected into the Airline Road to the New Brunsick frontier.