THEY CALLED IT PLEASANT STREET
A Brief History of First Settlement in Plainfield, Massachusetts, 1770-1800
Written by Dario Coletta
For more than a century following the English settlement of the Connecticut River Valley in Massachusetts, the lands to the west remained terra incognita to the colonists. This rough, hilly terrain stretching to the far western part of the state was Native American seasonal hunting territory. Following the end of the French and Indian War (1755-62), the area became safer to settle, creating an outlet for population pressures in the eastern part of the state. By this time the eastern Massachusetts towns had been settled for about six generations and land was at a premium. As a result, adventurous settlers flooded into these highland areas after the war.1 Anticipating this, the state divided the lands into town-sized parcels called plantations and set them up for auction. Plantation #5, which encompasses the better part of what is now Cummington and Plainfield, was bought in Concord by John Cummings in 1762 for £1800. It was then divided into roughly 100-acre lots and sold to proprietors. When a proprietor sold his lot he was required to set aside a one-rod (16-1/2 ft.) strip called a “vacancy” around the land for future roads. Plantation #5, as it was the farthest from established routes of travel, was the last to be settled.
Access to Plantation #5 was facilitated by a very early east-west road originating in Deerfield, which by the 1770s had penetrated the wilderness of what was to become Plainfield. This cross-county road was an early version of what is now Rt. 116. This short history will focus on what is now known as Pleasant Street in the Plainfield portion of Plantation #5. By the time it was officially designated and named by an act of the state legislature in 1877, this section of the old county road was well over 100 years old. By no means a straight way, it jogged and turned as was necessary. Coming from Ashfield, it enters Plainfield and runs two miles where it tees and turns north on what is now South Central Street. Today, Pleasant Street starts at Route 116 and ends at South Central Street. (The old county road continued up North Central then turned west onto Main Street, now Rt.116, ran through the center of Plainfield, and over West Mountain to Savoy.)
Early roads were little more than blazed bridle trails, but they allowed settlement to proceed rapidly as lots were sold off to the first settlers, who further developed the roads. Between 1781-1797 these pioneer settlers attempted four times to formally establish sections of Pleasant Street in town meetings, sometimes the same section more than once. This was necessary to enable the local community to take responsibility for road building and maintenance. By the mid-1790s Plainfield seems to have been in its most active settlement and road building phase. Between 1794 and 1797, 18 roads were accepted and 8 were abandoned. We will be concerned with settlement along the two-mile stretch that is now Pleasant Street during the period of 1770 to1800.
Once established, roads were generally two rods (33 ft.) wide, but this did not become mandatory in Plainfield until 1799. Once a road was accepted at town meeting, it was expected that abutters would build stone walls to flank the road, delineating the town’s two-rod right of way. Money was then set aside at town meeting for creation of the road bed and its maintenance. As early as 1795, roads were managed and maintained by road districts, and settlers were responsible for the roads in their districts. A road tax was assessed to each adult, although residents could also work on the roads in lieu of paying taxes.
The first yeomen on Pleasant Street appear on the earliest existing Cummington tax roll of 1784, Cummington having been incorporated in 1779.2 At the March16, 1785, Cummington Town Meeting the north part of the town was set off and incorporated as the District of Plainfield. The reason for this was that the residents of northern Cummington felt they had to travel too far for church services, crossing the unpredictable Westfield River with its rudimentary bridge, and then climbing a long, steep hill to worship at the Cummington Meetinghouse, church attendance being expected in all seasons.
This enumeration of Pleasant Street settlement will focus on the lives of these Cummington/Plainfield pioneers, moving east to west. However, any early history of Pleasant Street and Plainfield starts with the Dyer family, even though their farm was located in the town of Ashfield. The Dyer homestead still stands on the corner of Rt. 116 and Pleasant Street and remains a farm.3 Jesse Dyer (1769-1854) and his brother Benjamin were quite young when they arrived in Ashfield soon after 1790, and they settled in the far west of that town on 100 acres. Their descendants were numerous and influential in Plainfield through the 20th century, including sisters Arvilla and Priscilla Dyer who did most of the historical research that this essay relies upon. Their work, in turn, depended on that of their grandfather C.N. Dyer’s 1891 History of the Town of Plainfield. His book, as well as Bill Streeter’s Only One Cummington, were both indispensable sources for this document.
Jesse Dyer’s choice of location was likely influenced by the fact that his older sister had already married and was living up the street. Although his farm lay in Ashfield, Dyer attended church services in Plainfield as he was closer to the meetinghouse there. He married Sally Pool in 1795 and was appointed a surveyor of highways the next year.4 The Dyers had six surviving children, all of whom settled in Plainfield. Immediately west of their homestead, down the hill, the north branch of the Swift River crosses Pleasant Street from the north. Jesse Dyer built a dam, canal and sawmill up the stream on the north side of the road, parts of which still can be seen.
Continuing west into Plainfield, halfway up the hill from the stream on the north side of the road, is the site of Joseph Clark’s home.5 Joseph Clark (1750-?) and his family first appear in the Plainfield census of 1790 and again in 1800 with 3 and 6 children respectively. He was the older brother of Abraham and Jacob Clark, who settled further west up the street. When established in the 1780s, Joseph’s farm was located in a triangular plot that was part of neither Ashfield nor Plainfield. This is probably why he doesn’t appear on the early tax rolls. It wasn’t until the March 12, 1792 Plainfield Town Meeting that this triangle was added onto the southeast side of the town. Clark and his family did not stay long on Pleasant Street, however, and all traces of this farm have disappeared.
Moving west, the Shaw family settled on Plantation #5, lot #18, and the history is a little complex. In 1778, Jonathan Shaw Sr. (1720-1793) bought this 90 acres of land and divided it between Josiah Shaw (1758-1842) and John Shaw (1763-1841), likely his sons.6 Like many of the original Cummington settlers, they had emigrated from long established towns located in the southeast part of the state. Most came from the towns of Abington, Bridgewater and Weymouth.7
John Shaw settled on the very eastern boundary of lot # 18. (His brother Josiah settled on the opposite, western, edge of this roughly square 90 acres, approximately a quarter of a mile away, as will be discussed below). John Shaw married Hanna Dyer, Jesse Dyer’s sister, in Cummington in 1784, and their house on Pleasant Street was likely built about 1785. It burned in 1949 and a new cape was built on its foundation.8 John Shaw and Hanna Dyer had four children. Hanna died young and John remarried, staying on this street most of his long life, and like his (probable) father Jonathan Shaw Sr., he was buying and selling property in the east end of town for many years. In the period covered by this history, John was appointed hogreeve and surveyor of highways.9 He purchased a pew in the newly built meetinghouse for $22. Directly across the street from this house an old road can be seen running up the hill to the south. Long abandoned now, different sections of this road were accepted at town meetings in 1797 and 1798. It ran to what is now New South Street.
Traveling west from John and Hanna Shaw’s, exactly equidistant between the two Shaw homesteads on lot #18, another cape was built later, around 1795, about five years after Josiah Shaw left the area and his homestead was sold to Luther Packard (discussed below). This cape still stands though it is not inhabited or being maintained.10 It was possibly built for or by Tim Packard (1769-1853). Tim and two of his brothers, Luther and Perez, emigrated from Bridgewater, MA, and settled on the eastern side of Plainfield. In 1790 Tim married Aholibamah Curtis, daughter of Captain Moses Curtis from Bridgewater, an early settler in Plainfield. Tim Packard was appointed a surveyor of highways. The 1800 Plainfield census lists their family with seven members. Tragically, six of the family’s nine children died shortly after birth. In 1807, Tim was hired by the town to build the first stone animal pound for $39. He must have had considerable masonry skills to be contracted for this important job.
The road here curves to the north at what is now the intersection with Gloyd Street, which did not exist in the period under discussion. Just around the bend, on the western side of lot #18, lies the homesite of Josiah Shaw. The original c.1785 cape either burned or was moved and another cape was built in 1826 on the same foundation with an addition.11 Both the John and Josiah Shaw houses have 36′ by 30′ foundations and were built at about the same time, likely indicating the same builder. Josiah married Experience Hill in Cummington in 1783. In the relatively short time he remained in town, Josiah was appointed a surveyor of highways, but by 1790 he and his family had left Plainfield for the greener and less stony pastures of Meredith, NY. The house reverted to Jonathan Shaw Sr., his father.
A couple of years later, in 1792, Jonathan Sr. sold Josiah’s house to Luther Packard (1764-1796) who was a blacksmith and Tim Packard’s older brother. The property consisted of 40 acres and sold for £96, the price reflecting that it contained an existing house and barn.12 Likely, these 40 acres included the land that became the house lot next door for his younger brother, the aforementioned Tim Packard. Luther set up his blacksmith shop, was a surveyor of highways, and spent $35 for a pew in the meetinghouse. Unfortunately, he lived only 4 more years, dying in 1796 at the age of 32, leaving his wife Experience Hill and five small children.The 1800 census has the family heirs still living in the house.
Moving west, Pleasant Street intersects with Jones Avenue. Early roads could be ephemeral as well as changeable, and the development of Jones Avenue is a good example. At the town meeting of March 1786, a road layout plan was accepted that created northern access to Pleasant Street and Cummington from the recently established farms of John Jones13 and James Porter.14 This was the original version of Jones Avenue. When it was created, Jones Avenue ran south from the aforementioned farms and then forked at the bottom of the hill to reach Pleasant Street in an easterly as well as westerly direction. The eastern fork ran to Josiah Shaw’s house and joined Pleasant Street between his house and barn. The western fork climbed past Abraham Clark’s barn and house to Pleasant Street.15 It’s important to realize that this original county road (only later named Pleasant Street) continued to be used by the majority of travelers. For the neighbors to the north, however, this new section of road avoided steeper hills and a stream crossing. But it did not last and Jones was straightened to simply join Pleasant Street near where it does now. The removal of the forks is clearly stated in the spring 1797 town meeting transcript where the road was to be discontinued from “Abraham Clark’s to the Ashfield line where it does not run in the county road.” Therefore, it appears that about eleven years after it was established, this alternative version was removed.
Abraham Clark (1751-1832) established his farm on Pleasant Street west of Josiah Shaw’s house and Jones Avenue. He married Silence Gloyd, daughter of neighbor Jacob Gloyd Sr., in 1781 in Cummington, and they had nine children. Abraham paid $21 for a pew at the meeting house, was appointed hogreeve, fence viewer, and was part of the committee to build a school in the south district.16 In 1793, he was involved in a dispute with a neighbor, which was mediated by the church and resulted with apologies on both sides. Three years later, he was paid 4 shillings for work on the meetinghouse doors. Clark’s house burned in the second half of the 20th century and a ranch house was built on the foundation.17 The sidehill barn foundation for this Clark house is still to be found nearby, behind a new house.18
Further uphill on Pleasant Street we find the homestead of Abraham’s younger brother Jacob (1755-1832). They shared the 90-acre lot #13, and Jacob’s 40′ by 32′ cape still stands.19 Jacob Clark married Susannah Jones in 1782, daughter of neighbor John Jones, and they had 11 children. At the first Plainfield Town Meeting in 1785, Jacob was appointed tythingman, a church official.20 He also was town constable in 1791-2 and paid $26 for his pew in the meetinghouse.21
Continuing west from Jacob Clark’s, Pleasant Street intersects the northern end of Old South Street. This original road was laid out at a town meeting in the spring of 1792 and, as the name implies, ran south from Pleasant Street to what is now Cummington center. This area, part of lot #9, was initially settled by members of the Gloyd family.
Like his other middle-aged neighbors, patriarch Jacob Gloyd Sr. (1733-1804) raised his family in Abington and then moved to Cummington. His house site, just down from the intersection on Old South Street, is now a ranch house.22 Jacob was a widower, his wife Silence Richards having died in Abington the year after giving birth at age 40 to their ninth child in 1771. Jacob Gloyd Sr. is placed near this intersection in an early Cummington Town Meeting report of March 5, 1781 making him, along with Asa Joy, the earliest recorded settlers on Pleasant Street. He was a fence viewer and a surveyor of highways and on a committee with two other men to “hire preaching.” Near him, right at the head of Old South Street on the north side of the road, was the homesite of Gloyd’s son, Jacob Gloyd Jr..23 He married Rachael Blanchard in 1779 in Cummington and was a tythingman, paying $20 for his pew in the meetinghouse. He was also one of 12 men and women given rebates for home schooling his children in 1794.24
Moving down the hill on Pleasant Street from Old South Street, one comes to Meadow Brook. This is the second largest stream in Plainfield and was developed for industry early with several mills, including a cloth dressing shop run by Jacob Clark. At one point there was even a rooming house for about a dozen mill workers. Most of the evidence of the mills has disappeared over the years as industrial activity on the brook ceased by the Civil War period. Two mill foundations, however, as well as remnants of a dam and a flume, can still be seen just south of the bridge. On the north side, a large number of rectangular, level-bedded stones spilling from the embankment into the stream indicate the location of an earlier bridge.
At the April 5, 1790, town meeting it was decided to build a school in each of the three newly established school districts, to be finished by the following September and £60 was allocated for this task. So just west of Meadow Brook, on the north side of the road, Plainfield School #2 was established and opened that fall. Given this area’s fast-growing industry and population, the school’s placement was not coincidental. About 20 years after the establishment of this school, a cemetery opened across the street. It remained active for over a century; this appears to be a natural progression in newly settled areas. This cemetery yard holds the remains of most of the first settlement families and their descendants from Pleasant Street and the eastern end of Plainfield.
(The barn next to the cemetery and the cape across the street, #25 Pleasant Street, are not included in this history as they are not first settlement structures, although built around 1830.)
West up the steep hill from that farm, Pleasant Street is crossed by an old abandoned road that is still clearly visible; the northern section on the right lasted well into the 19th century. The section to the left, south of Pleasant Street, was discontinued as early as 1797. However, the homestead of Asa Joy (1754-1820) may well have been located on this intersection with Pleasant Street, as evidenced by a close reading of the town meetings’ minutes concerning acceptance of roads. Asa Joy married Mary Blanchard in Weymouth in 1773, and they had 16 children, 9 of whom died young. He was an early settler, listed in town meetings in 1781 and 1783, a veteran, and was appointed hogreeve at the first Plainfield Town Meeting. He spent $23 for his pew in the meetinghouse. However, this family lived in town only about 10 years before moving to New York. By 1792, Asa Joy is not listed on Pleasant Street.
Just above this, on the northeast corner of Pleasant and South Central Streets, was located the homestead of Jacob Joy Sr. (1735-1812), Asa Joy’s uncle.25 Jacob Sr. and his brother Isaac, who lived on what is now South Central Street and owned a tavern, were early settlers from Weymouth. Jacob Sr. married Jerusha Ripley of Weymouth in 1758 and they had four children. Once in Plainfield, he was appointed town warden in 1786 and town moderator in 1788.26 This homesite has remained a farm until the present day, but in recent years the farmhouse and barns have collapsed and been removed, although in the process a beautifully laid 20-foot deep, bell-shaped well was uncovered.
This is where the old county road turned right onto what is now known as South Central Street. Jacob Sr.’s son, Jacob Joy Jr. (1760 -1839), settled here, around the corner from his father. He married Susannah Snow in 1786 and they had nine children. He was a tythingman and a surveyor of highways. All three Joy family farms are now long gone.
This busy settlement period in Plainfield coincided with the War of Independence from Britain. The Pleasant Street settlers, the Clarks, the Joys and Luther Packard could have been called up for military service from their original home towns on the south shore of Boston or from Cummington, depending on whether they had moved west before the first alarm at the battle of Lexington and Concord on April 19th 1775. Militia men ranged in age from elders in their 60s to boys as young as 16. It was common for fathers to be joined by one or more of their sons, and this was the case with Jacob Joy Sr. and his son Jacob Jr. When the war began they were respectively 40 and 15 years of age. Joy Sr.’s nephew, Asa, would have been 21. Once in Cummington and Plainfield all men, unless exempted, were members of the militia and subject to an immediate call in an emergency.
By 1800 all these families, with a few exceptions, had set down roots on Pleasant Street. Within a span of only 25 years, they had turned a two-mile section of county path through first-growth forest into a vibrant community. This was during the uncertainty of the Revolutionary War and the economic difficulties of the post-war years. The men who came first married locally or returned to their families back home to marry and return to Plainfield with their brides. The families intermarried and grew rapidly. Communally they cleared the land, built their houses, roads, schools and church. They took responsibility for their actions in relation to each other by raising taxes and filling town positions. And by these actions, most importantly, they contributed to and helped develop a democratic civic life in Plainfield.
- Now known as “the hilltowns,” this area stretches from the Housatonic River to the Connecticut River Valley in western Massachusetts. ↩︎
- A yeoman was a farmer who owned his own farm. ↩︎
- Plainfield Road, Ashfield, currently owned by W. and J. Meservey. ↩︎
- A surveyor of highways surveyed and mapped out road routes. Plainfield appointed between 8 and 10 surveyors to cover the town. The majority of men on Pleasant Street held this position for at least one year. ↩︎
- Other than the Dyer house, all the early homes on Pleasant Street were capes and were placed on the north side of the road in order to maximize the light and warmth on their facades. ↩︎
- Unlike Josiah, a direct link between Jonathan Shaw Sr. and John Shaw has not been established. ↩︎
- Already middle aged when he arrived from Abington, Jonathan Shaw Sr. settled with his wife and seven children on Stage Road, south of lot #18. Records show that he was involved in numerous real estate transactions in Plantation #5 starting in 1771, many of them involving the Farr family. ↩︎
- 151 Pleasant Street, currently owned by T. O’Sullivan and P. Bouricius. ↩︎
- A hogreeve was entrusted with preventing and appraising damage by stray hogs. Often the youngest and least high status of local men were chosen for this position. They would ensure that all hogs were yoked and had a nose ring to prevent rooting and burrowing. By the late 18th century few towns elected them by that name. Most years hogs were not allowed to run freely in Plainfield. ↩︎
- 137 Pleasant Street, currently owned by David Locke. ↩︎
- 123 Pleasant Street, currently owned by D. and R. Coletta. ↩︎
- The original price for the entire 90 acres of lot #18 had been £70 in 1778. ↩︎
- 47 Jones Avenue, currently owned by J. and K. Pugliese. ↩︎
- 43 East Main, currently owned by H. Purseglove. ↩︎
- When I first moved to Pleasant Street (the Josiah Shaw homesite), Arvilla Dyer asked me if I had ever seen any evidence of an old road which would have passed between my house and barn. At the time I said that I hadn’t, but a few years later I realized that a boundary wall running from Jones Avenue along the back of R. and J. Green’s field (107 Pleasant Street) curved up inexplicably between my house and barn. I believe this single stack wall is one side of this discontinued road (see map). ↩︎
- A fence viewer, upon request, would inspect stone or wood boundary fences and settle disputes concerning straying livestock. ↩︎
- 91 Pleasant Street, currently owned by D. and T. Shearer. ↩︎
- 95 Pleasant Street, currently owned by R. Baker. ↩︎
- 71 Pleasant Street, currently owned by R. Sadowski . All the earliest surviving houses in Plainfield are full second-story 40′ by 32′ capes. ↩︎
- Tythingmen maintained order in church and collected tythes; usually two men were chosen. Their duties were varied, ranging from collecting church taxes to detaining people on the roads on Sunday who were not traveling to church. ↩︎
- The constable kept the peace and maintained order in the community. He would levy and collect all fines and execute all town warrants. ↩︎
- 8 Old South Street, owned by P. and S. Carpenter. ↩︎
- A possible cellar hole can be seen here. ↩︎
- All nine Gloyd children settled on the east side of Plainfield with several sons further down Old South Street. C.N. Dyer’s history mentions that the Gloyd brothers were all physically large, heavy men and that Joseph had to have a door frame disassembled to remove his 300+ pound body from his house after his death. ↩︎
- 1 Pleasant Street, currently owned by J. and R. Wooldridge. ↩︎
- The town warden was a town official, in charge of all church-related matters, income, records, etc. The moderator, which every town still has to this day, presided over town meetings and insured they ran smoothly. ↩︎




