From Cowpaths to Highways

Prior to the Town of Fairfield’s purchase of approximately 52,000 acres of land from Native Americans during the 1660’s, the land that now comprises Easton was unsettled. The early colonial families from Britain were mostly a sociable lot, mainly divided only by their particular brand of Christianity. They weren’t inclined to head off into Connecticut’s hinterlands in search of better farmlands than could be had closer to the coast where there were established churches and merchants to trade amongst. It was the division of the newly acquired long lots that began the interior expansion of Fairfield, and much of that expansion was slow to materialize. What is now the Town of Easton consisted of fifty of the original long lots that were awarded to the land holding families of Fairfield based upon the size of their taxable estates in 1681. While all the lots were similar in depth, the width was determined by the relative wealth of the original grantees. Nathan Gold was awarded the widest parcel at 879 feet, while orphan sisters Phoebe and Deborah Barlow received the narrowest strip of land at only 31 feet. Access to these lots would be by a series of upright highways that were bounded by the Stratford Town Line on the east and the Mile Common on the west. A total of five upright (north-south) highways in what would become today’s Easton were surveyed in 1714 and the rights-of-way mapped out for their eventual construction. The Stratford Town Line Highway (today’s North & South Park Avenues) had a 99-foot right-of-way, followed by Jackson’s Highway (Sport Hill Road) at 74-feet, Morehouse Highway at 83-feet, Wilson Highway with only a 51-foot right-of-way and Burr Highway with 99-feet. Morehouse, Wilson, and Burr were never fully constructed, nor regularly maintained along their entire length, and some of the rights-of-way in the original grants were either abandoned or exchanged for alternate ones during the 19th century.

While the town granted the rights-of-way for these highways, it didn’t provide much in the way of funds for their construction. The surveyors were tasked with gathering enough men – generally the property owners who would benefit from those roads – to cut the pathways that would provide access to the land. Initial roads were not roads at all, the land was simply cleared of enough trees to allow livestock and ox drawn carts access to the interior. These “cowpaths” were often strewn with stumps and large rocks, making travel slow and tedious whenever carts or wagons were involved. Maintenance was non-existent at first, and bridges were slow in coming; usually built at the expense of those who benefited most from their construction. Luckily, the upright highways had very few river crossings that required actual bridging to be passable for most of the year. The earliest bridges weren’t much more than felled tree trunks bound together that spanned the waterways, often only used when the rivers were running high and too deep to safely ford with an ox drawn cart. They were prone to wash away during spring floods and rapid ice melts and were replaced much more often than their European counterparts.

Settlement of the North Fairfield Parrish (Easton) was rather slow in coming. East-west travel was mostly non-existent during the first quarter of the 18th century. There were a few cowpaths and old Native American trails, but nothing in the way of actual roads. In 1724, the first three of what would become the five cross highways in Easton were surveyed and laid out. The first cross highway ran along what would now be Congress Street and Jefferson. The second cross highway ran west from the Stratford line across Flat Rock Road, Beers Road and North Street. The third was essentially made up of Adams Road, Center Road and Westport Road.

Ten years later, the fourth and fifth cross highways were surveyed. Number-four closely followed today’s Church Road, then north on Sport Hill Road to Silver Hill Road. From there it ran west where in connected to Black Rock Turnpike and then south until it then turned west again over Freeborn Hill. The fifth cross highway ran west across Rock House Road and then connected to Den Road where it continued to Valley Forge in Weston. The latter two cross highways appear to more closely follow trails that were already established when they were surveyed.


Easton HSE Long Lots Highways Reeve 2009
North Fairfield long lots and highways with dates on a map overlay done by Stuart Reeve for the 2009 Historical and Archeological Assessment of Easton


By the mid-1700’s, the population had grown large enough to require at least a minimum amount of road maintenance. Road surveyors were again tasked with recruiting – willing or not – local men to repair the roads. Failure to appear for roadwork resulted in a trip before the local justice of the peace. While most of the recalcitrants were given a stiff warning in lieu of a fine, they were also then required to report for road duty. This occurred during two time periods each season: late April through early June and mid-September through mid-October.

By the early 1800’s, the area boasted some of the worst roads in Connecticut. Easton was then part of Weston and in 1801, the town passed a tax of one cent on every dollar of assessed property to be specifically used to repair the town’s roads.

It wasn’t enough.

In December of 1802, the levy was raised to three cents per dollar. The tax could be paid in either currency or labor. The spring labor rate was set at sixty-seven cents per day for a man and his tools. If he chose, in addition to his labor, to supply “a yoke of oxen, cart and chains, or a plow, he would be paid one dollar and thirty-four cents.” Those rates dropped to fifty cents per day for labor and tools, or one dollar for the man and his oxen during the fall season. Timbers needed for bridges were directed to be purchased by the surveyors and they then were reimbursed by the town.

Easton HSE Morehouse Highway looking S (2)
Morehouse Highway looking south from Center Road c.1907

During the first half of the 19th century, several private corporations were established and granted charters for the establishment of privately held turnpikes supported by tolls. A definite financial relief for the town, but not particularly popular with the general populace. Several of these turnpikes operated in Easton during that time span. Sport Hill Road, Valley Road, parts of Black Rock Turnpike, Westport Road, and the main road (current State Route 59) to Monroe were all supported by tolls. One by one, these companies began to falter and the roads were then taken over by either the state or the town during the middle to late 1800’s.

State maintained roads were the first to see pavement in Easton. Such as it was anyway. Early hard surfaced roads in town were covered with a mixture of oily tar and sand. If you are old enough to remember this miserable process, enough said. If you’re not, suffice it to say that it was an environmental nightmare with oil and tar running off into every stream and swamp near the roadways that were covered in this fashion.

State aid helped the town with bridge building and road improvements throughout the first half of the 20th century. In the1940 fiscal year alone, the state appropriated $10,000 in aid to maintain and improve town owned roads. That year the entire highway account was given a $24,500 budget, so the state was contributing a full 40% in addition to the roads where they covered 100% of the cost of construction and maintenance (today’s Black Rock Turnpike, Center Road, Sport Hill Road and the section of Route 59 between Union Cemetery and Monroe).

It wasn’t until after WWII that Easton established a full-time highway department, complete with enough equipment and manpower to maintain the town’s constantly growing number of roads. And it was well into the 1950’s when the last of the dirt roads that the town maintained were finally paved. What we take for granted today was over 250 years in the making.

Information for this post was obtained from various Easton Town Reports; the 2009 Historical and Archeological Assessment of Easton written by Stuart Reeve, Kathleen von Jena and David Silverglade; the Read Family Papers assembled by Stuart Reeve in 2000; and various records of town meetings from the Towns of Fairfield and Weston between 1681 and 1850.


  1. Great article! Love all of this info. Wondering how the purchase was made from those indigenous to this land, in the 1600s? Is there any info on That?

    1. There is and that will be told in a future post that outlines the basic conflicts between English law and culture with that of the Native Americans who once lived here.

    2. All of the lot dividends- and many details of the upper Long Lots given to the early Fairfield settlers are detailed in Elizabeth Schenck’s “The History of Fairfield – From the Settlement of the town in 1639 to 1818” Volume I. It’s also searchable with dozens of mentions of the words “Long Lot”. Both volumes are available and downloadable online at . The Fairfield Museum and History Center also holds a very large map of all the various lots with the original owner’s names, including all of the early families of Fairfield and Black Rock. The Concord Settlers who arrived with Rev. Jones received the “Eastern Long Lot” land grants now in Easton, such as Wheeler, Bennett, Sherwood,

  2. Nice article, thank you. During my youth growing up in the 1950 and 60s Weston, the history of road development was never explained, the names of roads such as Cross Highway or Long Lots never given any context. We learned how to get about from school bus routes, and visiting friends on bikes, a process of osmosis. By the time we had drivers licences all the roads were mapped out internally, but I remember new people arriving and finding the lay of the land very perplexing.

    I regret that my parents’ generation expressed little curiosity or enthusiasm and seemed to feel no need to educate us about the town history, about the old farms and families that were quickly disappearing as the new generation of suburbanites washed over the landscape.

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