For many early sailors, it was the first land seen approaching this continent. It is nearly the most seaward island. Its seacliffs, while also nearly the highest, are the steepest. The rock that is the island formed a few hundred million years ago from molten rock as the earth's crust jostled about. Vegetation took hold. Over many millennia, the ocean rising and falling with temperature shifts made a marsh alternately a fresh water marsh and a salt water marsh. The result is a record of these changes scientists can translate.
Early on Monhegan was a focal point for fishermen. Plymouth Plantation sent a ship in 1624 to Monhegan for dried fish to get them through the winter. The captain of the ship reported that when he arrived, there were more than thirty "ships that fished," in the cove at Monhegan. Early explorers gave it various names, some called it Whale Island, a reference to its shape seen from the water. One and a half miles long, north to south and three-quarters of a mile wide, the surface is domed in both directions, thus making it easy for mariners in the days of considerably larger sea animals, to come up with the name. A couple of years at sea, living on whatever they could find and eating anything living or otherwise when they failed to find better, might have contributed to the illusion.
There is evidence that fishermen and explorers from Italy, England, Portugal, France, and Spain, including the Basque region, knew of the island. They noted its location, in writing and on charts typical for the period, as early as 1390. The first English description of Monhegan was by David Ingram, who sailed with Captain John Hawkins' expedition to the Spanish Main. In October 1568 he was marooned on the shores of the Gulf of Mexico. Haw- kins, through loss of ships and provisions, was forced to set 100 sailors and soldiers ashore. Most went south, but Ingram and two others started north. They traveled on foot over Indian trails along all of what is now the east coast of the United States. They may have known of the annual visits by fishing vessels to what Verrazano, and for 150 years other Europeans, called Norumbega, which was the area around Penob- scot Bay. They reached a river later described as being "60 leagues from Cape Breton." This could have been the Penobscot. At this river they boarded a French ship, the Gar- garine, and sailed for Harve, France in 1569. In English court of law documents, Ingram described going by canoe with an Indian to Pemcuit (Pemaquid). There he saw "a great island backed like a whale." He said he first took it for a whale, "as those fish in that country are easily taken for islands at a distance."
There is less documented evidence of earlier European contact. The most publicized and challenged of these are the inscriptions in rock on Manana, the small barren island a half mile west of Monhegan, that in part forms the other side of the harbor. Some claim they are Norse runes, a kind of marking system and a few believers claim the origin to be ancient Norsemen or Phoenicians. It's not the only place in Maine or New England with mysterious inscriptions in stone. There does not seem to be a much better explanation for any of these other inscriptions, either for who did them or when. The markings at Manana are at least an indication that someone was there a long while ago making lines in stone unlike anything the native inhabitants made. A shipwrecked and stranded fishermen, going bonkers marking off phases of the moon or passing ships that didn't see him, could as easily be the origin as could a Phoenician surveyor.
The name of the island has almost as mysterious a background. The Mohegan Indians are a suggested source, but it is only one of a long list of names attached to the island. Bits and pieces used from the six or seven languages, including the native two or three, have been sources of speculation. One story of the origin traces the name to Monaghan County, Ireland. Many of the English interested in the colonization of this part of North America were also interested in the colonization of Ireland. Sir Humphrey Gilbert, with a grant in 1578 of land from 30 degrees to 40 degrees latitude, was soon actively engaged in the New Found Land. He had been in service in Ireland as a governor from 1566 to 1570. Sir John Popham of the ill-fated colony west of Mon- hegan, was also interested in Irish colonization. Hugh Wirrel, who helped establish English colonies north of Virginia, had settled a plantation in Ireland called Mona- ghan. This could have easily come to sound like Monhegan. Then, of course, there are those very early Irish voyagers of legend.
The earliest clear reference to the island is a 16th century Italian chart showing the island's location at 43 degrees. Englishmen were reported to be living on Monhegan by a Spanish governor, as early as 1588. By 1608 there was an established fishing station on Monhegan. The Englishmen found it a good location, being off shore in the fishing grounds, close enough to shore to also trade furs, yet further than Indians were willing to take their canoes to attack the outpost. Monhegan was where the settlers at Plymouth went to load a ship with dried fish to survive difficult winters.
Eighty years later the settlement was flourishing. France and England were at war and the French had formed an alliance with the Indians. In October of 1689 the French sent their Indian allies, aboard a frigate, to attack Monhegan. The inhabitants apparently escaped, there are no known records of what happened. It would have been difficult to surprise the island, as the approach would have been seen far in advance.
The settlement, the oldest English settlement in New England, was destroyed by fire. Charred wood was later found in many old cellars. There is a record of one resident returning to his burned cabin. Records of Massachusetts towns show the date of destruction by way of the arrival of some of the inhabitants.
Fishermen came back after a while and residents on the mainland came in the summer to catch and dry fish. But the long siege of five Indian wars kept the owners from coming back. People stayed on Monhegan for the summer in the early 1700s to avoid Indians, and returned in the fall to the mainland. The wars ended in 1763. In 1777 a Kittery cabinetmaker, Henry Trefethren bought the island for 300 pounds. Trefethren, a revolutionary soldier, died in 1807 and is buried on Monhegan. The property was divided among his heirs, a son, two daughters and wife. It is back to these owners that all the island property is now traced. After the American Revolution, Trefethren built his homestead and it stands today. Others followed, others remain. Monhegan continues to be well suited as a fishing community.