Roads, Common Ways and High Ways, Part I
A brief excursion along the early roads of New England. Connecticut Road, a Country Road by any other name.
A Road
October, 1721
“Be it enacted by the Grovernour, Council and Representatives, in General Court assembled, and by the authority of the same, That from and after the first day of November next,
...That all such rum as shall be imported or brought into this Colony and landed or offered to sale in any of the roads, harbours, creeks or rivers thereunto belonging, without first paying the duty aforesaid to some naval officer of this government, shall be forfeited, the one-half to the informer that shall prosecute the same to effect, and the other half to the use of this Colony.” (Public Records of the Colony of Connecticut, May 1717 to April 1726. Pages 282, 283)
June, 1727
“...it was voted 1 that the road layd out by majr Wolcot & mr Conant begining at ye eas sid of willamantick river against Nys dwelling house being ten rods wide and called Majr Wolcots Road running to the east sid of the town shall ly and remain for a country road for ever...” (Proprietor's Meeting, June 20, 21, 1727. Willington Records, Book B, Page 41)
The word road as sometimes found in seventeenth and eighteenth century Colonial New England documents is often spelled phonetically as rod, rood, rhod, rhode, rode and like variants. The antecedents can be traced back to Old English raad, raat, rād, rodu and Middle English roode, rod, rōde, rāde and rhoade.
A road, in the nautical sense, is the course a boat or ship rides. This sense of riding can be found in the term roadstead: a place where a vessel rides at anchor. A rode (n.) is also a chain, cable or rope, tied to the anchor. Rode (v.) is the past tense of ride. The movement or act of riding can be seen with OE strēamrād (stream + road), where water rides over the course of a stream-bed, a riding of water, to put it another way, a run of water.
As encountered in seventeenth and eighteenth century documents and writings, a road is defined as a riding. Seaward, the journey of a boat riding the waves and landward a journey of a rider on horseback traveling cross-country. This country riding can be seen in OE rād-hors, a riding horse. In Colonial New England such a riding would have most likely been on a trotter or pacer. One of the breeds of sure gaited ponies used for cross-country travel such as a Fell Pony, Palfrey or the Welsh Pony or Cob.
A landward road then might be seen as a course or way convenient to riding. A roadway, a riding way, a bridle path.
In southern New England, in the early 1630s, the first English settlers or planters appropriated existing ancient foot-paths and used these as riding ways, both within and between their coastal plantations or settlements.
These riding ways or bridle paths became official town High Wayes as well as colony Common Ways also known as Country Roads. These riding ways emanated from the coastal settlements, gradually pointing inland, reaching out from the earliest Massachusetts Bay Colony towns of Charlestown, Newtowne, Watertown, Boston, Roxbury, Sagus, Salem, Wessagusset and Dorchester, inland to Concord by 1635, Dedham by 1636, Sudbury by 1639 and Nashaway, present day Lancaster, by 1643 with the siting of a trucking (trading) house on George Hill.
Routes connected Massachusetts Bay with distant settlements such as Providence, at the head of Narragansett Bay, and the Connecticut River towns of Wethersfield and Springfield by 1634, Windsor by 1635 and Hartford by 1636. The 1630s riding way to Springfield from Boston was called the Connecticut Path, sometimes referred to as Connecticut Road. From Springfield, the path pointing back to Boston was called the Bay Path.
The names and terms used in period documents to identify these common ways varied by author and date, and could vary within the same document. How a specific road was identified often depended on the insular perspective of the writer, such as with the Connecticut Path, aka Bay Path. These descriptions depending on where one started out and what the intended destination was. One finds frequent mention in town records of what would seem to be a singular “road to the Meeting House” that emanated from the outlying farms in every corner of the town.
The following description of one of the inland Nipmuc settlements is taken from a tract by John Eliot of Roxbury, it mentions the riding way to the settlement and illustrates the sometimes narrow English view of the countryside connected to the Bay.
The quote is from Daniel Gookin's Historical Collections of Indians in New England, the preface is dated December 1674 (original spelling and grammar retained, followed by a rough translation into contemporary usage):
“Haſſanameſitt* is the third town of praying Indians. The name signifieth a place of ſmall ſtones, This place lieth about thirty eight miles from Boſton, weſt ſoutherly ; and is about two miles to the eaſtward of Nipmuck river ; and near unto the old road way to Connecticut.
*Now generally pronounced Haſſanamiſco, Grafton.” (Gookin, Historical Collections - Pages 184, 185 (25, 26 of 49))
Hassanamesitt* is the third town of converted christian indians. The name signifies a place of small stones. This place is located about thirty-eight miles south-westerly of Boston and about two miles east of the Nipmuck (Blackstone) River, near the old way to Connecticut. *Now generally pronounced Hassanamisco, Grafton.
Daniel Gookin’s description for the bridle path passing Hassanamisco, taken from John Eliot, as being the old way to Connecticut reflected that by the time of his writing, the primary route from the Bay to Connecticut had changed. While the old road remained in use, there was a “new” route to Springfield on the Connecticut River, as Gookin relates in a description of Okommakameſit (line breaks added):
“There is an Indian village, within twenty eight or thirty miles of Boſton, weſtward upon the road to Connecticut, called Okommakameſit, alias Marlborough, which lieth very near the centre of moſt of the praying villages.
This Indian plantation joineth unto an Engliſh town called Marlborough so that the Engliſh and Indian plantation bear the ſame name. In this Indian plantation there is a piece of fertile land, containing above one hundred and fifty acres, upon which the Indians have, not long ſince, lived, and planted ſeveral apple trees thereupon, which bear abundance of fruit ; but now the Indians are removed from it about a mile.
This tract of land doth ſo imboſom itſelf into the Engliſh town that it is encompaſſed about with it, except one way ; and upon the edge of this land the Engliſh have placed their meeting-house ; which is an argument to demonstrate that they look upon it as near the midſt of their town, according to general computation and practice.
This parcel of land, with the addition of twenty acres of the neareſt meadow, and a woodlot of about fifty acres, is well worth two hundred pounds in money : and yet the Indians will willingly devote it for this work : for it brings little or no profit to them, nor is it ever like to do : because the Engliſhmen's cattle, &c. devour all in it, becauſe it lies open and unfenced ; and while the Indians planted there, it was in a fort fenced by them ; yet by their improvidence and bad fences, they reaped little benefit in those times ; and that was one cause of their removal.” (Ibid, Page 220 (43 of 49))
A Connecticut Path, Wayland to Springfield
In the period circa 1634 to 1648, the route of the riding way called Connecticut Path or Connecticut Road changed. Although the physical path or course of the route changed, it continued to be called the path to Connecticut or Connecticut Road. The 1634 route to Springfield past Hassanamisco was superseded by the new 1648 route through Marlborough.
The initial route, apparently marked and used by some of the earliest English travelers to Connecticut, ran from Watertown to Wayland, around Lake Cochituate, crossing the Sudbury River in Ashland, and continued through Hassanamisco Country to Hopkinton, Upton and on to the Blackstone River crossing at or near Farnumsville, south of Grafton Center, west of Keith Hill. By the time Daniel Goodkin was writing in 1674, this route would be viewed as the “Old” Connecticut Path. The old road wasn’t abandoned as it was apparently used at least in part by Daniel Gookin and John Eliot in their Fall 1674 trip to the Nipmuc Praying Towns.
The old path to Springfield, From Keith Hill in Hassanamisco Country continued through at least part of what was known as Shetucket Country, via Sutton, Oxford, Charlton, Sturbridge, Brimfield, Palmer, Monson and Wilbraham, following along the Chicopee River into Springfield.
Connecticut Path, a branch to Hartford
The old Connecticut Path to Springfield branched just east of Oxford with a leg running south westerly through what was later known as Wabaquassett Country. This branch passed Plaine Hill in Woodstock and ran west, crossing the Still River near present day North Ashford. A bridle path from Plaine Hill across the West Hill in Woodstock was called Connecticut Road in 1691. The early 1634 route might have crossed the Quinebaug River at Quinebaug, continuing west through North Woodstock.
After the old path crossed the Still River, it branched in present day North Ashford with one leg leading west to the Freshwater Plantation, present day Enfield. Later records called this path Enfield Road. This path passed a hill called Lead Mine Hill, mentioned by Springfield’s William Pynchon.
From the fork in the path to the Enfield Road, the route ran southwest and was called Hartford Road until 1718. This bridle path to Hartford crossed the Willimantic River about a half mile above a place called Owwaenunggannunck. On the west side of the Willimantic River, Hartford Road parted with a branch pointing to Windsor. Hartford Road continued southwesterly to the outlet of the cedar swamp near Bolton Notch (present day Bolton Lakes) where it joined the path from Providence (also referred to as Connecticut Path in some sources) and continued through Bolton Notch to Hockanum.
Connecticut Path, Sudbury to Springfield
As Daniel Gookin described in his locations of the several Praying Towns, The new road to Connecticut passed through Wayland, Sudbury, Marlborough, Worcester, past Quabaug Pond, through the heart of Nipnet Country to Springfield including a branch pointing to Northampton.
The Marlborough path through Quaboag country to Springfield was apparently in use circa 1645, with the route noted as being marked by the English and in official use circa 1648. The process of marking of the ways, essentially copying the traditional native method, is noted in a letter by John Eliot to Henry Whitfield. In Eliot’s letter entreating Whitfield for more financial and material support, Eliot describes a desire to go to Namaske (Namaoskeag or the falls at Amoskeag), a traditional gathering and fishing place on the Merrimack River. There was an English trucking (trading) house located at Nashaway (George Hill, Lancaster) at the time [brackets mine]:
“the Indians way lyeth beyond the great [Merrimack] River which we cannot passe with our horses, nor can we well go to it on this side the river, unlesse we go by Nashaway, which is about, and bad way, unbeaten, the Indians not using that way ; I therefore hired a hardy man of Nashaway to beat out a way and to mark trees, so that he may Pilot me thither in the spring, and he hired Indians with him and did it ;” (Whitfield, 19)
Given the early narratives about travel, both locally and back and forth cross country, it seems that the footpaths assimilated by English travelers and settlers were marked and in regular use by the English well before these routes were officially recorded in colonial documents.
Travel was essentially seasonal and depended on route options. There were paths fit for single riders, pack horses or driving livestock. It is likely that a variety of routes between the Bay and Connecticut were in simultaneous use early on, from Newtowne, Dorchester, and Roxbury, to Springfield, Windsor and Hartford, as well as the paths from the Bay to Providence and Providence to Hartford and New London. The following are excerpts from the diary of John Winthrop, Governor Massachusetts Bay Colony, 1630 - 1634, 1637 - 1640 etc. :
"1633 sep - John Oldham and three with him went over land to Connecticut to trade;" (Transactions and Occurrences, page 53)
"1635 8 oct - About 60 men women and little children went by land towards Connecticut with their cows, heifers and fwine, and after a tedious and difficult journey, arrived fafe there." (Ibid, page 89)
"1635 9ber 3 - There came twelve men from Connecticut, they had been ten days upon their journey and had loft one of their company drowned in the ice by the way, and had been all flarved. but that by God's providence they lighted upon an Indian wigwam. Connecticut river was frozen up the 15th of this month." (ibid, Page 90)
"1635 Mo 11 - This month one went by land to Connecticut and returned fafe." (Ibid, page 92)
"1636 Mo. 3 25 - Mr. Hooker, paftor of the church of Newtown, and the reft of his congregation, went to Connecticut ; his wife was carried in a horfe litter, and they drove 160 cattle, and fed of their milk by the way." (Ibid, pages 100, 101.) (Ed. The comment that Hooker's wife rode on a "litter" would suggest that she rode aside on a planchette saddle, a chair with a footrest, i.e. an early version of a side-saddle. The litter was perhaps noteworthy as the use of a pillion, or riding astride, might have been more common.)
"1637 Mo. 6. - Mr, Hooker and Mr. Stone came with Mr, Wilfon from Connecticut by Providence and the fame day Mr, Ludlow, Mr.Pincheon & about twelve more came the ordinary way by land," (Ibid, pages 135, 136)
Some of the information about these early colonial riding ways can be found in colonial government records. However, the details for the act and process of assimilation of the ancient paths as Town Highways and the Colony Country Roads, and the details of their physical courses, is generally found in town records.
Continued with Part II
Mark A. Palmer
Municipal Historian, Town of Willington
Shetucket Country, Eastern Algonquia
Excepting all materials in the public domain or provided under a Creative Commons Public License; Original content © 2025, all rights reserved.
References:
Ashford, Town of, Ashford records.
Boston Public Library, Norman B. Leventhal Map Center. Nova Belgica et Anglia Nova, Willem Janszoon Blaeu, 1635.
Bowen, Clarence Winthrop, The Boundary Disputes of Connecticut, Boston 1882.
Burt, Henry M, The First Century of the History of Springfield, The Official Records from 1636 to 1736, Vol I, Springfield, 1898.
Chase, Levi Badger, The Bay Path and Along the Way, Norwood, 1919.
Connecticut General Assembly. The Public Records of the Colony of Connecticut, from: May, 1678 to June, 1689. J. Hammond Trumbull. Hartford, 1859.
Connecticut General Assembly, The Public Records of the Colony of Connecticut, from: May, 1717 to October, 1725, Lib. Charles J. Hoadly, Hartford, 1872.
Crane, Ellery Bicknell, Historic homes and institutions and genealogical and personal memoirs of Worcester County, Massachusetts, with a history of Worcester society of antiquity; New York, 1907.
Eliot, John; A Brief Narrative of the Progress of the Gospel Among the Indians of New England in the year 1670, London, 1671; Boston, 1868.
Eliot’s description of Hassanamico:
“Haffunnimefut is the next Town in order, dignity, and antiquity ; fundry of our chief Friends in the great work of Praying to God, came from them, and there lived their Progenitors, and there lieth their Inheritance, and that is the place of their defires. It lieth upon Nichmuke River ; the people were well known to the Englifh fo long as Connecticot Road lay that way, and their Religion was judged to be real by all that travelled that journey, and had occafion to lodge, efpecially to keep a Sabbath among them. The Ruler of the Town is Anuweekin, and his Brother Tuppukkoowillin is Teacher, both found and godly Men.” (A Brief Narrative, Pages 26, 27)
In the fall of 1674, John Eliot and Daniel Gookin traveled through Nipmuc country installing men they had chosen to serve as ministers, teachers and constables, responsible and reporting to English authorities, eliminating the traditional roles of the Powwow and Sachem. The role of teacher was that of one who saw that the established Puritan dogma was adhered to. From Gookin:
This year again on the 14th of September last, 1674, we both took another journey. Our deʃign was to travel further among them and to confirm their ʃouls in the chriʃtian religion, and to ʃettle teachers in every town, and to eʃtabliʃh civil government among them, as in other praying towns. We took with us five or ʃix godly persons, who we intended to preʃent unto them for miniʃters. (Historical Collections, Page 189 (27 of 49))
In the summer of 1675, Metacom led a revolt against English incursions in Wampanoag country and many in Nipmuc country followed suit.
Gookin, Daniel, Historical Collections of the Indians in New England, Cambridge, 1674, Sandwich 1792. Special Collections (Miscellaneous). Paper 13. https://digitalcommons.uri.edu/sc_pubs/13.
Grafton, Town of, Documenting Hassanamesit Woods, Its History and Cultural Resources, the Town of Grafton Hassanamesit Woods Management Committee, Grafton, 2006.
Judd, Sylvester. History of Hadley Including the Early History of Hatfield, South Hadley, Amherst and Granby Massachusetts. Springfield, 1905. Web.
Lawson, Rev. Harvey M., The History of Union Conn, Founded on Material Gathered by Rev. Charles Hammond, Principal of Monson Academy, Compiled by Rev. Harvey M. Lawson. New Haven, 1893.
“In 1633 John Oldham, the first European who ever traveled this section, obtained from the Indians in this vicinity some specimens of black lead or graphite. It was found in two places in this vicinity; one in Sturbridge, near Mashapaug, the other on the hill called Ocquebituque, south of where Mr. Henry Corbin now lives, and lying partly in Union and partly in Ashford. As early as 1644 they were known to William Pynchon, the founder of Springfield. He describes the one in Union as being "five or six miles south of the one in Quassink (Sturbridge), in Tantousque, and the lead is of better quality." This mine was considered quite valuable. As early as 1657 the General Court of Massachusetts Bay granted the land upon which it was situated, as a reward for public service, to Captain Thomas Clarke, of Boston, “ (History of Union, 36)
Lincoln, William. History of Worcester Massachusetts, From its Earliest Settlement to September 1836, With Various Notices Relating to the History of Worcester County. Worcester, 1862.
Nourse, Henry S. Early Records of Lancaster Massachusetts, 1643 – 1725. Lancaster, 1884.
Temple, J. H. History of North Brookfield Massachusetts. North Brookfield, 1887.
Town Reconnaissance Survey Reports, Massachusetts Historical Commission, 1979 – 1987.
Whitfeld, Henry. A farther Discovery of the Present State of the Indians in New-England, Concerning the Progresse of the Gosple amongst them. Manifested by Letters from Such as Preacht to them there. London, 1651.
Willington, Town of, Willington Records.
Winthrop, John, A Journal of the Transactions and Occurrences in the Settlement of Massachusetts and the other New-England Colonies, from the year 1630 to 1644. Ed John Porter, Hartford, 1790.
Woodstock, Town of, Woodstock Records.