Roads, like celebrities, diet fads, and clothes, fall out of fashion and into obscurity more frequently than is supposed. The Old Post Road, King’s Highway, Pequot Trail, Stage Coach Route, whatever you want to call the various incarnations of the coastal road from Boston to New York, has changed over time as certain parts were bypassed in favor of newer, straighter roads, or were rerouted as bridges were built in more convenient places, or simply were neglected when a newer route proved more economically viable. Often the oldest roads are still present near or even directly adjacent to the newer road. Sometimes parts of the older roads were utilized in the construction of the newer “model.” And sometimes the old road has literally remained a dirt path in the woods.  Although parts of the old road have been obliterated by the construction of a housing development (in Sharon, MA) or broken up by the addition of a parking lot to the back of a building facing US 1 (in Norwalk, CT), most of the oldest sections of the old road from Boston to New York still survive. The difficulty sometimes lies in finding out where the old road is, and sometimes in figuring out which description of the old road is the most accurate. There are often many red herrings and misleading names, some of which continue to confuse people about the true nature of the post road from Boston to New York.  Perhaps the most misleading name is the name given to much of US 1 in Connecticut, Boston Post Road, which is a source of endless confusion to those who wonder why I spend most of my time on roads not called Boston Post Road if that is the name of the project on which I labor.

           The 1920s was a time of great change in America, led by the rapid rise of the automobile as the major form of transport. Cheap, affordable cars produced by Henry Ford and others allowed even people of more modest means to be able to purchase a family car.  The movement of all of these new automobiles was severely limited by the poor roads of the country, basically unchanged since the mid-nineteenth century when the railroad became the dominant means of transport. The highways of the United States were essentially built for stagecoaches and, with the exception of the turnpikes built in the first decades of the new republic, would not have been much different from the roads Alexander Hamilton traveled in1746.

        Many turnpike projects were undertaken in the early nineteenth century, as the roads in Connecticut (as we have seen from the descriptions of Knight, Birket, Hamilton, Finlay, Washington, and most every traveler of the colonial period) were considered to be virtually impossible to travel.  Although legislative approval for a new turnpike was often easy to win, many of these projects were unpopular with the citizens of the towns through which they passed as the road builders were often given the right to plan a road and then have the town pay for the bridges and land purchases necessary for construction of the road.(1)  Nevertheless, many new roads were built, or should I say, many old roads were rebuilt to make them straighter.  The turnpikes charged a toll which many travelers balked at paying by either sneaking past the toll gates or by continuing to use an older road whenever possible, a practice called “shun-piking.” By the late nineteenth century, every toll road in New England had gone bankrupt leaving the care for the roads in the hands of states which had little interest in their upkeep as it was seen as money poorly spent.

        By the Twenties the situation had become intolerable and demand for new road construction, or at least road improvements, to handle the burgeoning automobile traffic had reached an apogee. And so began an era of road-building, starting with the most famous of the “new” roads, the road from Maine to Florida that followed the Atlantic Coast, which is still known as US 1.(2)  The builders of this road often took the straightest parts of older roads and linked them with new stretches that bypassed the centers of towns as often as possible to keep the traffic moving. The great public works projects that were created in response to the Great Depression by the Roosevelt Administration, allowed this road-building orgy to continue unabated until the advent of the Second World War. 

        The 1920s was also a period of renewed interest in colonial America: this is when historical villages such as Colonial Williamsburg and Old Sturbridge Village were developed into the tourist attractions they are today. This nostalgia for things colonial is reflected in the name given to many stretches of the newly rebuilt road through Connecticut, also known by the somewhat uninspiring name of US 1: Boston Post Road. This explains to a large degree why I very infrequently travel on Boston Post Road even though this project is nominally about following the Post Road: much of what is called the Boston Post Road was built in the twentieth century. If a segment of the older road was utilized in the new road I travel on it; otherwise I avoid US 1 whenever possible in favor of the older road, which is usually more interesting in any case.

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       The roads in Milford are a good illustration of the complexity of the history of  the road from Boston to New York. That there were two roads from Milford to New Haven in 1789 is clear from the statements of George Washington in his diary. On October 17, 1789, President Washington traveled to New Haven via West Haven on what was called the “lower” road.(3)  Upon his return to Milford on November 11, 1789, Washington “Set out about sunrise and took the upper road to Milford it being shorter than the lower one thru West Haven.”(4) Today the two roads roughly correspond to route 162 from Milford Center to West Haven (the “lower” road) and the Boston Post Road (US1, the “upper” road). The “upper” road no longer truly exists as it fell victim to the builders of the Milford Turnpike in 1802, who were extremely unpopular in Milford as they laid claim to large tracts of land that were already occupied by farmers in the town. Nevertheless, the road was built, and it straightened the kinks out of the old road. (5) There are still vestiges of this old road as the upper road also followed what is now New Haven Avenue until it crossed the Indian River, after which it diverged to the northeast on what is now Gate Lane. After this the route of the original road becomes murky.

        On the other hand the lower road from Milford to New Haven is mostly the same road as it was in colonial Connecticut.  This road was the route I followed in the last entry, diverting from the main road today in only a few small segments, including the final few hundred yards on Buckingham Avenue, today the “back alley” of many of the businesses lining New Haven Avenue as it reaches the Wepawaug River in Milford Center (see the photo above).  Heading west from the center of Milford is slightly more complicated, and that is the direction in which I am heading.

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        In early America main roads still passed through the centers of towns as this was where the commercial activity was centered. On the other hand, the planners of the Boston Post Road in the twentieth century deliberately rerouted the road around the centers of towns to avoid congestion.  This led to commercial development outside the centers of towns, and the construction of the interstate highways in the second half of the twentieth century exacerbated this trend. It was here in Milford that this trend began in earnest with the construction of a shopping mall at the junction of Boston Post Road and Interstate 95 called Connecticut Post Mall.(6)  Thus the Milford Turnpike, despised by the residents of Milford whose land was seized, at least went through the center of town, while the Interstate and US1 both skirted the town center and shifted commerce away from it. As early as 1939 a history of Milford noted that the “ Boston Post Road, constructed in 1932...rerouted through traffic and relieved congested conditions in the center of Milford...the old Boston Post Road, still passes Milford Green, but is used chiefly by local traffic.”(7)

        Today Milford center is happily not a desolate wasteland despite the presence of the mall only a few miles away. Milford is lucky to have a pleasing architectural landscape with an abundance of high quality residential buildings to attract an affluent population who patronize the numerous small restaurants and stores and cafes that line River Street, the main commercial street west of the river, and other nearby streets. Other cities have not been so lucky as we have seen.

        Milford’s roads are somewhat confusing to untangle as the town was settled around the river in a peculiar manner that resulted in the presence of two streets flanking and running parallel to the river as well as two streets flanking and running parallel to a smaller creek a little distance west of the river called West End Brook. To connect these two areas of settlement there was a road on the south side, today’s Broad Street, and a road that curved in a southwest direction from the northern area settlement on the Wepawaug to the northern end of the settlement on the creek to the west, today’s West Main Street.

        The first meetinghouse was built at the north end of the Wepawaug River settlement on the west bank and it was here in 1641 that the first bridge was built across the river as “the river was too deep to cross except by fords, of which there were many. The crossing was easy for riders...but difficult for those on foot...a church site had already been selected at the junction of West Main and River Street...and a bridge (at that site) afforded easy access to church for those living across the river, and successive bridges at this point have been appropriately called “Meeting House Bridge.”(8)  Thus the main road through town became West Main Street and it was here in 1654 that the first tavern was built by Henry Tomlinson “so that the town might not be destitute of acomodation for travelers.” (9)

        A second bridge was built in 1648 on the site of what is now the Memorial Bridge where New Haven Avenue meets the Wepawaug River, and so it is likely that the traveler had the choice of crossing either bridge and following the roads on either side of the river to the meeting house where a left turn led the traveler through to the tavern and on to the Housatonic River on the west border of Milford.  It is entirely plausible that the traveler from New Haven might have crossed at Memorial Bridge, continued on Broad Street, and met the old Country Road to the ferry at the Housatonic River, bypassing West Main Street entirely. Yet the presence of a tavern from an early date on the more northerly West Main Street indicates that the main traffic flowed through that street instead. Clark’s Tavern, a later Milford tavern, was also sited near the meeting house, and it was here that Washington stopped in 1789 on his tour of New England.

        A second tavern run by John Camp had come into existence in 1705 on West Town Street, on the western edge of the town, and still another tavern run by a Samuel Miles existed from 1710 on West Main Street. The common denominator in all these various taverns is that they were all on the West Main Street route through town.  The construction of a turnpike leading away from Milford center to the Housatonic River rerouted traffic away from West Main Street and onto Broad Street. Thus, according to a nineteenth-century writer, by the “beginning of the present century (i.e. 1802) Broad Street has become the major east west thoroughfare,” and a milestone on the western edge of Broad Street is a symbol of that transformation. (10)

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        A second milestone, which can found somewhat to the north of the meeting house on Maple Street and River Street, is illustrative of the pitfalls of believing everything you read. This stone (see photo below) has a plaque which reads “Milestone on Original Boston Post Road set by order of Benjamin Franklin, Postmaster General, 1735.”  I call this the milestone of the three lies. It is very unlikely that the Boston Post Road passed this way for reasons I have already stated. It is also unlikely Benjamin Franklin placed this stone for at least two reasons: first, he probably did not place any milestones contrary to the lovely story as I have discussed in previous entries, and second, he did not become postmaster of Philadelphia until 1737 and was not deputy postmaster of North America until 1753.(11)  A third reason I think this stone is a red herring is that the inscription, which says, presumably, NH, is carved in such a neat hand that it is completely unlike any stone from the colonial era that I have ever seen; I suggest it is either from the era of stagecoaches and turnpikes in the early nineteenth century, or that it is completely fake. As regards the plaque and its assertions, I am put in mind of Jake Barnes’s comment at the end of The Sun Also Rises : “Isn’t it pretty to think so?”

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        Following the old road from New Haven to New York through Milford is thus quite a convoluted route: first I leave New Haven Avenue, and I follow Buckingham Avenue the final few hundred yards to reach the Wepawaug River. I cross the Stone Bridge and follow River Street on the west side of the river (although I also could follow Prospect Street up the east side of the river) to the meeting house on West Main Street, with a small detour over the Meeting House Bridge, and another short side trip up West River to the “milestone” at Maple Street. Then I follow West Main Street as it curves down to intersect with Clark Street, which I cross to follow Washington Street until it peters out just short of today’s Boston Post Road.  On older maps of Milford the old road is referred to as the Old Country Road. Later maps from the nineteenth century show the Old Country Road merging with the New Haven and Milford Turnpike which followed the course of Broad Street from Milford Center and continued west to cross the Housatonic River. The old road, the turnpike road, and US1 all run along the same track today, which is called Bridgeport Avenue where the roads come together. Where Washington Street dead ends I am forced onto Boston Post Road, which skirts Milford Center to reconnect with the original road here west of the center. My first experience with Boston Post Road west of Milford is extremely unpleasant as I am forced onto a narrow shoulder of the road as it crosses the railroad tracks, with cars screaming past within a couple of feet away from me.

        The old road would have continued in a direct line leading from Washington Street but for the current Boston Post Road and the railroad tracks which split the road into two. Following Boston Post Road until it joins the old turnpike road and becomes Bridgeport Avenue, I discover the final small vestigial piece of Washington Street, the old road, behind a Subaru dealership on Bridgeport Avenue and today little more than a dead-end back alley behind the car dealership. After this the old road ends as we know it. It is difficult to know the exact course of the old road west from Milford at this point as there has been so much road rebuilding along this stretch. So I opt to follow Bridgeport Avenue the final two miles to the Housatonic River.

        The rest of the trip along Bridgeport Avenue is more pleasant than my initial experience with US1. Although the strip of road here is primarily lined with car dealerships and fast food restaurants, there is a sidewalk.  I head in the direction of the setting sun as hundreds of starlings swirl overhead and gather on the electric wires above me. The road is not completely straight as I would have expected from a turnpike road, lending some credence to the idea that this may in part be the original road. After a mile of commercial development I reach an area of older residences and then, much to my surprise, the road becomes narrower and passes through a pleasant village called Devon, lined with old street lamps, cute shops, a couple of bars and restaurants, and brick sidewalks.

        Old histories of Milford refer to the road from Milford to the ferry across the Housatonic as Witch Road, but I can find no evidence of such a road. The ferry was located somewhat near the first bridge built across the Housatonic River, the Washington Bridge, built at the same time as the development of this road into a turnpike in 1802. This bridge was rebuilt several times, most recently in 1921, as a plaque on the bridge informs me. The ferry had existed since 1650, so for over a century and a half, horses and people were ferried across the wide river to and from Stratford and Milford in a flat-bottomed scow, originally for the price of a halfpenny per person and twopence for a horse or other beast.(12)  A tavern also existed here at the ferry from at least 1761.(13)

        There is a pleasing curve in the road as it reaches the Washington Bridge. From the bridge the railroad bridge is visible to the north as is the Interstate 95 bridge to the north. To the south the wide river leads to Long Island Sound, and the town of Stratford is visible along the west bank. Crossing the river, I leave Milford and New Haven County and find myself in a very busy commercial area at the intersection of US1 and Interstate 95 in Stratford in Fairfield County, the last county in Connecticut along the post road. Ahead of me is a Staples and a BJs Wholesale, among many other big box stores. Happily, Ferry Boulevard veers left away from this area toward the center of Stratford, about a mile to the south. Ferry Boulevard is still US 1, and for a few hundred yards the traffic stays with me. Shortly I reach a junction with East Broadway, the old Ferry Road that leads into Stratford center. This is a much quieter residential road that is much more pleasant to walk along. As I cross a grassy patch between East Broadway and Ferry Boulevard, I spy a milestone set in the middle of the patch. It turns out to be an extremely interesting stone that begins the final stage of my walk through Connecticut and sets up the entire remaining 73 miles to New York. But you will have to wait until the next entry to find out about that.