Scouting a Place for a Settlement

Source: “Overland to Connecticut in 1645: A Travel Diary of John Winthrop, Jr.” The New England Quarterly (September 1940.)


John Winthrop, Jr. was the son of Massachusetts Bay Colony’s first governor John Winthrop. He settled both Saybrook and New London. Read more about Saybrook during the Pequot War in Venture Smith’s Colonial Connecticut.

In 1640, the Massachusetts Bay Colony gave Fisher’s Island to Winthrop, and in 1644 he received a grant of land across from Fisher’s Island. The excerpts from his 1645 travel diary below describe his exploration of a possible place to locate the settlement that became New London.

Winthrop was a man of many talents. He later became governor of the Connecticut Colony and helped the colony get its royal charter in 1662. He was also an early scientist. He was interested in minerals and mining. He experimented with making salt by evaporating sea water. He was also a physician. Find out more about him at

In November 1645, Winthrop travelled overland from Boston, across Massachusetts to Springfield, south to Hartford and Old Saybrook, and then east along the Connecticut shoreline. 

Here are excerpts from his travel diary describing what he saw and encountered along the way. The first river towns of Hartford, Windsor, and Wethersfield had been settled in the 1630s, and so were about a decade old when he travelled there. 


November 17. Monday. About 10 o’clock or a little before, we started for Hartford. The small streams were frozen over so that they would hold both us and our horse. We had to wait a long while for the ferry to take ourselves and horse to Windsor so that it was [afternoon] even before crossing the river [probably the Farmington River]. On the main road in Windsor we crossed on a ferry where there had formerly been a bridge, but this had been swept away by a flood. The whole day was pleasant but cold before night. Master [Matthew] Allyn accompanying us to the part of the correct route where it is easy to go astray, we reached Hartford about 9 o’clock and the [inn] of our host Thomas Ford. 


How long did it take Winthrop to travel the 27 miles from Springfield to Hartford?
What obstacles did he encounter along the way?


November 18. Stayed at Hartford. The governor and the officials had gone to their country place in Tunxis [Farmington.].


Winthrop travelled the next portion of his trip on foot, leaving his horse in Hartford.


November 19. Wednesday. Having got a [Mohegan] Indian to carry our things, I set out for Saybrook by land. For the river was frozen over so that the boats … were tied up, not having enough water even before it froze. … We crossed the Matabeset and other small streams on the ice and reached the  house of an Indian named Wehasse, where we slept that night in the house of an Indian named Seanuxut. Cold and fair all day. 


November 20. Thursday. Reached Saybrook a little before evening. Clear and cold.


November 21. Stayed by Saybrook. Clear and calm. … A boat crossed to the west. It started a little after midnight to rain. 


November 22. Stayed at Saybrook. Cloudy, A boat … came from the west and dropped anchor before the harbor on the eastern side.


November 23. Sunday. The boat tried to enter the harbor but sailed in slowly. Finally it could not enter and dropped anchor again. After dinner, however, Elias Parkman, as captain, came with a ferry, accompanied by a merchant, John Tinker,  and Mr. Williams from Windsor with some sailors, the boat having been left with three sailors, namely, Frost, Hadfre, and a boy. During the night a wind arose and a driving rain, so that there was a great storm, and as a consequence the boat, whose anchors did not hold so well (for it lost its biggest anchor a little earlier near the island called Coninecut, alias Fishers Island), was driven to shore, but on a sandy spot, with no rocks, the captain and the other remaining at Saybrook.


November 24. Monday. Wind W(est). There was a strong swell on the sea. I was so hindered because of the wind and the fall of the tide that I could not cross the river, fearing that the ferry might be driven on a sandbar.


November 25. Wind, W[est-}S[outhwest], blowing violently. About 10 or 11 o’clock I crossed the river with the waves so high that they often came into the boat with great violence. I was afraid that the ferry would hit bottom in which case without a doubt it would suddenly be filled with water. The water was not deep, often the oars scraped bottom and once or twice if I am not mistaken, when the waves subsided, the ferry did touch in one spot. But with God’s help we reached the shore safely, where we met the captain and two others who told us about the ship. We went to see the boat which was being tossed dangerously on a rock but not [harmfully] unless a N[orth-]N[ortheast] wind came. That night we came to an Indian fort at Niantic but the Indians were all away [from] their homes. I fell into the stream about up to my waist.


Based on what you have learned about Native American life ways, why were there no people at the fort at Niantic when Winthrop got there?


November 26. Wednesday. A little after daybreak journeying near Nameag we found some little Indian houses and one of the Indians guided us to Nameag [a Pequot village where New London is today]. All that day we crossed over land looking for a suitable spot for a colony. The night was very cold.


November 27. Wind N.W. About 10 o’clock leaving [Thomas Peter] and the rest behind, I crossed in a canoe with one man Jo. R. and an Indian [who was] guiding us, by the name of Sabin. A meeting having been arranged with [Pequot Sachem] Robin [Cassasinamon] who had served before, I crossed the river and the stream Poquanuc, where Robin told me there was fruit-bearing land without rocks, arable with a goodly number of planting fields. I crossed also the River Mistick, accompanied hither by Robin and his brother, who then returned to Nameag with my letter to Mr. Peters. I stayed here about an hour, lighting a fire, eating, and writing. About [afternoon] we neared the river Pacatuck, but as the usual place [for crossing] was frozen and yet not everywhere solid enough, I could not cross on foot or by canoe, the part being frozen where the canoe usually could cross. But, by the providence of God, there was an Indian on the other side and he pointed out for us a place about a half mile below where we crossed on the ice safely, while some Indians watched us crossing. As darkness came we entered the house of an Indian, Cutshamekin, a relative of Robin, [later] being taken to the house of George, whose wife was formerly a woman of Momonottuck. We slept in comfort. 


What do you think Winthrop thought would make a good location for a colony?
What do you observe about the relationship between Winthrop and the local Pequot?


November 28. Friday. I remained at George’s house, because nearly all day there was rain, hail, and much snow. About 3 o’clock it got calm, etc.


November 29. Saturday. Fair weather, the wind Northerly & a little E[asterly] towards night. We lodged at Notoriope [in] his wigwam near the great pond, the water runs thence into Pacatucke [River.] We were come about 20 miles from Mimbago where we [lie.] Saw [Pequot Sachem] Wequashcooke only as we passed by his house. 


From here, Winthrop passed into the Rhode Island colony and Narragansett country. He returned the following year to found the settlement now called New London. 


Source: “Overland to Connecticut in 1645: A Travel Diary of John Winthrop, Jr.” The New England Quarterly (September 1940.)


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