Updated: Jun 5, 2021
The movement to the west had already begun before the middle of the 1700s. The next attractive river valley west of the Connecticut River was the Housatonic, a smaller river that runs south from Vermont through Massachusetts and Connecticut, just east of the New York border, and empties into Long Island Sound at Stratford.
Major Talcot's fight with the Indians is one the earliest historical events to occur in this part of the country. In August 1676, at the end of King Philip's war, Maj. John Talcot, who had been stationed at Westfield with a body of troops, pursued a party of fugitive Indians to the banks of the Housatonic where they overtook them and inflicted a severe defeat upon them. Twenty-five of the 200 or so Natives were killed and 20 were taken prisoner. This event apparently happened just north of Sheffield. It’s not known if any of the residents of Westfield participated in the pursuit.
In 1722 Massachusetts authorized the establishment of two townships, the Upper and Lower Housatonic Townships, each seven miles square, running north through the Housatonic River Valley from the Connecticut border. Captain John Ashlely of Westfield was named a member of the committee authorized to admit settlers and to grant lots in this new frontier. The committee was to choose one hundred and twenty petitioners who they considered to be the most likely to found a permanent settlement. Those selected would have no more than three years to build and occupy a home and to cultivate at least 12 acres of land. For each hundred acres assigned, the grantee would pay thirty shillings, which in part would be used to pay the Natives for their land.
In 1724, Konkapot, the sachem of the Mohicans, and twenty other Natives deeded to the settling committee a tract of land extending from four miles east of the Housatonic River westward to the colony of New York. The agreed price was £460, three barrels of cider, and thirty quarts of rum.
Matthew Noble of Westfield was the first to cross the Berkshire mountains to explore this new territory. He was about fifty-seven years old when he came to the Lower Housatonic in the fall of 1725. Finding the Natives friendly, he spent the winter with them and returned to Westfield in the spring to make a report. He went back to the Housatonic again in June, accompanied by his daughter, Hannah (carrying her feather-bed with her on horseback). Later, Matthew was joined by his six sons and two remaining daughters (including Hester, whose daughter would marry Daniel Gunn II).
By May of 1727 many people were said to be settled upon land along the Housatonic where Sheffield, Great Barrington and Pittsfield are located. At this point, the Dutch filed a complaint claiming prior rights to the land. This conflict between the Dutch of the New York colony and the English of Massachusetts would continue for some years. As a consequence, a half dozen years passed before encouragement was again given for more settlers to move in. In 1733 the House of Representatives ordered John Ashley, Ebenezer Pomeroy and Thomas Ingersoll to form a committee and “bring forward a settlement of ye uper Township att Housatunnock.”
It’s not certain when the brothers Alexander and Daniel, and their cousin Capt. Stephen Gunn left Westfield to settle in a new township in the Lower Housatonic called Sheffield, but it was sometime shortly after 1734. In fact it appears certain that Daniel Sr., his wife Hester, and their three youngest children—Mary, Daniel Jr., and Alexander—are among the first to arrive in the new settlement. Records show that Mary Gunn weds Capt. David Whitney in Sheffield in September of 1739.
Sheffield in 1741 extended from the northern boundary of Connecticut 10 miles up to a line crossing the HousatonicRiver in a place that became Great Barrington. Sheffield was what had been referred to in records as the LowerTownship. The Upper Township contained Great Barrington and Pittsfield.
Alexander and Daniel II, the sons of Daniel Gunn, along with their cousin, Stephen, a son of Aaron Gunn, and Reuben, son of Thomas II, soon marry the daughters of other settlers of the Housatonic. Alexander marries Elizabeth Owen in Sheffield in 1751 and Stephen marries Eleanor Ingersoll in Great Barrington in the same year. Daniel marries Esther King in Great Barrington about 1753, and in 1756 Reuben marries Mercy Stiles in Pittsfield. Moreover, we know of another Gunn in the area. He is also named Reuben and was possibly a son of Captain John Gunn, which would make him a 2nd cousin of these four men. He dies in Pittsfield sometime after 1765. Alexander has six children born in Sheffield, Daniel five, and Stephen six. So, there is a sizable clan of Gunns living in Sheffield for at least three decades, until after the Revolutionary War.
John Ashley, the son of Captain John Ashley, became a prominent citizen of Sheffield. He graduated from Yale in 1730 and held a number of important posts in the community, including justice of the peace. He was later to become a Colonel in the South Hampshire Regiment of the state militia. His “Justice Docket 1772” shows the sort of problems brought before him by the people of Sheffield. There were complaints of physical violence and quarreling, of theft and cattle rustling, and the case of a young lady who on 20 May 1784 appeared before him with her family: "Then many Gunns appeared and made oath that she was pregnant with a bastard child begotten on her body by Theoffilus Jhide begotten in the month of August last …” [This document is preserved in the Sheffield library, and a copy is held in the Sheffield Genealogical Society] It’s not known how that case was decided, but the young lady in question was Mary Gunn, the daughter of Alexander. It may be that it was this same Mary and Reuben Callender who filed marriage intentions in Sheffield on 3 March 1790.
Rumors of an impending attack by Natives, referred to as the “Great Alarm,” spread panic along the Housatonic valley in September 1754. Ashley, then a Captain, led his troops to the defense of Stockbridge and Pontoosick (Pittsfield). But only two Natives were ever sighted and the valley would never again be invaded. Later, during the time of the French and Indian Wars, Sheffield contributed men to the militia. A number of citizens built fortified homes, but there is no evidence the village was ever in danger.
The first town meeting at Pittsfield was held in 1761, at which 3 selectmen were elected and men were named to various other posts: a constable, 2 wardens, 2 fence-viewers, and 2 deer-reeves. One of the two deer-reeves was Reuben Gunn, almost certainly the son of Thomas Gunn of Westfield. He married Mercy Stiles, his 2nd wife, in Pittsfield on 6 May 1756 and died there sometime after 1765. The births and baptism of his 5 children by Mercy are all recorded in Westfield records. It’s not clear if the family actually lived in Pittsfield or not. Settlers did not begin living there until 1752. 
Small numbers of Europeans from the Hudson RiverValley had moved into the Sheffield area late in the final quarter of the 17th century. Black settlers were not uncommon, many freed or escaped slaves from the Dutch but probably also some from the English colonies. By far the largest group, though, were 3rd and 4th generation English settlers from Westfield beginning in the 1720s. “Sheffield” was a name given by this last group to the entire area in the southwest corner of Massachusetts, parts of which were later separated into other towns, including Stockbridge and Great Barrington.
The agricultural land available in the narrow Housatonic Valley limited the size of the farms. They tended to be relatively small and not usually productive enough for growing cash crops. In 1771, the largest of these farms had only 50 cultivated acres. It was a property of John Ashley, who employed three teams each of oxen and horses in its operation, animals in numbers no other farmer in town could claim to own. But Ashley’s 50 cultivated acres were an extraordinarily high exception and some families tilled as few as one or two, their remaining acreage typically divided among wood lots, orchards, hay fields, pastures and kitchen gardens. Daniel and Esther Gunn’s farm of 88 acres exemplified this division of land usage with 20 of them in grains and the remainder given over to the other uses just mentioned.
The first settlers found some open meadow lands along the Housatonic River, but most of the tillable soil was created out of the surrounding forest. They often started out with small, cultivated patches interspersed with girdled trees, later they would be chopped down and burned to clear more land for agriculture. The men spent their days chopping, burning and dragging stone in order to clear land. But 1765 the best land was taken and the farms of Sheffield supported 172 families, 125 houses, and a total population of 1,073.. Miller 19-20.]
The animals they kept served multiple purposes. The chickens, turkey, ducks and geese ate the destructive grasshopper and other harmful insects in addition to supplying eggs, feathers, and meat. Pigs ate farm and family refuse, and also supplied hides and meat. Cows and goats supplied milk, butter, cheese, hides, and meat; and in addition to meat and hides the sheep supplied fiber to make cloth. Goats and sheep were the most common animals (in 1771 there were 1,701 in Sheffield). Pigs were the next most numerous (528), then cows (500), horses (320) and oxen (304). The free-roaming pigs were particularly important, and every family had at least two or three.
Apple trees were planted everywhere and by the 1770s they stretched along the river on both sides for 40 miles between Sheffield and Kent. No family was without its supply of apples, which stored well through the winter, could be dried and preserved, and made into the ever-present cider. The town produced 423 barrels of cider in 1771.
Hay was produced on every farm and its harvest was done manually and was very labor intensive. Once the hay harvest was done, farmers turned to harvesting oats, rye, wheat, corn and potatoes (the latter came to America late, but was produced in Sheffield by the 1760s). It was rumored to have aphrodisiac qualities and was not mentioned in the Bibles, so it was regarded with suspicion and somewhat shunned by many of these descendants of puritans (as was the tomato).
Plowing was usually done by oxen. It was hard and slow work, so only about an acre could be plowed in a day. Those who did not have draft animals, might arrange the use of a neighbor’s in exchange for labor or some product. Most farming implements were made of wood, and even plows did not always have an iron tip.
The organization of the farm family continued as it had always been. The responsibilities of the wife and female children extended from the hearth, kitchen and house to the garden and farmyard. This was their domain, and it included care of the smaller farm animals. They attended to all household chores—cooking, cleaning (including making soap), sewing, spinning fibers and weaving, washing and repairing clothing, making butter and cheese, gardening, and caring for the fowl and pigs in the farmyard (including their slaughter). The men of the family were responsible for the larger animals and they labored mostly in the orchards, fields and woods beyond the farmyard. They planted and harvested crops, cared for fruit trees, built and maintained tools and fences, and prepared the winter’s wood supply (a family might require 20 cords, cut by axe alone). If the farm itself did not supply adequate meat for the family diet, the men also hunted. The one activity which was often the responsibility of both sexes was milking the cows and goats. 
Very few cooking utensils were available for cooking, sometimes only a “dinner pot, a dish kettle, a tea kettle, a frying pan, and a bake kettle,” but often not even all of these. In some households the most expensive objects were the pots and kettles. . The only items for cooking owned by Ester Gunn in 1763 were an iron skillet and two iron pots,
Up until the Westfield immigrants started coming, the main trail to the outside world from Sheffield went west to Kinderhook, New York. The main route into Sheffield following its incorporation in 1733 was from Westfield. It came into used in 1735, but it was clearly more of a path through the woods than a road. The “proprietors” of the new road were quite proud that “whereas, before it was very difficult for anybody, and to strangers almost impossible … to find the way, now by our having marked a sufficient number of trees … an entire stranger cannot easily miss it.” In other words, this was simply a footpath, with no bridges, drainage, grading or improvements of any kind. Walking was, in fact, the mode of transportation used by most people, so a footpath was apparently adequate. Few people could afford the luxury of a horse. We know that as late as 1771 there were only 320 horses in Sheffield for a population of about 1500.
1. The History of Great Barrington, 1880.
2. Preiss, 11-12.
3. Preiss, 12.
4. Preiss, 15.
5. Preiss 17.
6. The history of Pittsfield (Berkshire County), Massachusetts, Volume 1, p 134 by J. E. A. Smith, Boston, Lee & Shepard, 1869. He was possibly the son of Captain John Gunn.
7. See History of Pittsfield, Vol I - in Google Books.
8. Miller, James R. Early Life in Sheffield, Berkshire County, Massachusetts (Sheffield Historical Society, 2002) p 11.
9. Miller, 15.
10. Miller, p15 from Gunn family file, estate inventory of Daniel Gunn. Pruitt, Bettye Hobbs, editor, The Massachusetts Tax Valuation List of 1771, pp. 472-479.
11. Miller 19-20.
12. Miller, 17.
13. Miller, 18.
14. Miller, 18-19.
15. Miller, 20-21.
16. Beers, p.62.
17. Earle, Home Life in Colonial Days, p 56.
18. Berkshire County Probate Records, Daniel Gunn Jr., inventory, p. 772.
19. Earle, p. 51.
20. Earle, p. 52.
Wasson, Joanne F. Tales of Old Deerfield,78 pages of anecdotes about the history of Deerfield; mostly republished columns that appeared in newspapers.
Chester D. Stiles, A History of the Town of Westfield (reprint of original 1919 publication by
J.D. Cadle & Company in Westfield, Mass) BiblioBazaar, 2009., Vol. I pages 594 and 595. See Google Books: http://books.google.com/books/about/A_History_of_the_Town_of_Westfield.html?id=zH_aQgAACAAJ.