The western entrance to New Haven is much less complicated than the way into the town from the east.  For one thing there is only one river to cross and not a wide one at that. There were two roads that led out of town to the west: one called Derby Road which led due west to Derby on the Housatonic River about ten miles inland, and the Milford Road, which led southwest out of town to the town of Milford, about 11 miles away on the coast.  The Milford Road was the major road from the earliest date of settlement, and this is the road that was called the Post Road or the King’s Highway in the colonial era. 

            The path to New York out of New Haven is pretty clear. Wadsworth’s map of New Haven from 1748 shows one road leading southwest away from the Green near the intersection of George Street and High Street. The beginning of this road is now lost to the redevelopment of the area around Frontage Road, but it is easily traced through the modern roads to the other side and continues along what is today Davenport Avenue, which heads directly for the West River Bridge, where it crosses into West Haven and on to Milford. Before I continue with a more detailed description of the road to Milford after crossing the West River Bridge, I will first describe the portion of the old road that traverses the southwestern area of New Haven.

*****

        There are dozens of sites in New Haven listed on the Connecticut Register of Historic Sites--none of them are on or near Davenport Avenue. To reach this street from the Green involves a slight detour to account for the lost piece of road resulting from the Frontage Road development and the expansion of the Yale Medical complex.  As the original nine squares of New Haven were laid out in the 1630s, it really does not matter which route I take to get to Davenport Avenue, so I opt for York Street as it is the closest street to my starting place, the Book Trader Cafe, where I have a coffee and pastry amidst the books while planning my walk.  I follow York Street from Chapel Street for two blocks out of the center of New Haven, where I cross under a parking structure on Frontage Road and enter the warren of buildings comprising the Yale University Medical Campus. Once upon a time I visited the campus on a recruitment visit for graduate school and learned how not to hold a recruitment session for potential graduate students. The faculty are top-notch world-class scientists and their work should speak for itself, but every major graduate program was vying for the talented students that had assembled at the Sterling School of Medicine one bitterly cold January Sunday morning. The students had all arrived the night before and were treated to a couple of hours of blaring music and some free beer at some student’s house. At precisely eight a.m. the next morning proceedings began. No thought was given to the fact that we might not have eaten breakfast before our arrival, and the “moderator,” a faculty member who shall remain nameless, proceeded with hardly two minutes of “welcome to our school.” The schedule called for four speakers, followed by a break of fifteen minutes, then four more speakers, etc., for about four hours, after which lunch was scheduled. The moderator went first and spoke for twenty minutes longer than the scheduled fifteen minutes, which pretty much set the tone for the next half dozen speakers.

        Now one or two faculty talks on obscure research in crystallography or genomics is one thing, but four talks in a row with no breakfast early on a Sunday morning with no bathroom break for an hour and a half is beyond the pale.  There was open rebellion by the beginning of the second session, in what came to feel like the Attica prison riots: first some student asked if we could stick to the schedule, which met with vigorous nodding approval of the other dozen or so candidates; then someone asked if we could have a chance to get some coffee, at which point the moderator called in the program manager and chided her for not providing refreshments--she seemed stunned we had not had a chance to eat breakfast. Coffee arrived forty-five minutes later, but the damage was done.

        The most amusing portion of the whole morning was watching one student who initially was extremely engaged and vocal (and who seemed to have some form of Asperger’s Syndrome or something that caused her to  be completely oblivious to the presence of other people in the room).  After the third or fourth speaker she seemed to slow down, and by the fifth speaker, her head had drooped and she was snoring quite loudly--in the front row! She was awakened and proceeded to fall asleep again for the next hour or so, much to the amusement of the other candidates who were happy for any diversion from the endless parade of Nobel laureates presenting canned versions of their research in excruciating detail. At least that is how it seemed to me, someone who had had no breakfast, who had drunk too much the night before, who had to go to the bathroom, and who already knew after walking York Avenue to this godforsaken corner of New Haven that there was no way he would spend four or five years in the future making the same walk to that soulless neighborhood.

*****

        Davenport Avenue starts at the hospital complex, and the change in atmosphere is immediately apparent. The neighborhood is called The Hill and was once known as Sodom Hill. Recent Census 2010 data provide a demographic picture of what is clearly a poor neighborhood judging from the modest houses: the area through which I pass after the hospital complex is Census tract 1406 and contains 5,060 of New Haven’s roughly 123,000 inhabitants. 9% are White (non-Hispanic), 48% are Black, 40% are Hispanic (of any race), 1% are Asian, and 2% are Other groups). The neighborhood is rundown, and I am pretty happy to reach the West River after a fifteen minute stroll down Davenport Avenue. Here Davenport merges with Congress Avenue (US1), which was built later as the Milford Turnpike, a straight road leading directly from New Haven to Milford over the steep hills ahead.

        The bridge over the river provides a moment of scenic relief, with views of salt marsh extending away in both directions and a couple of great blue herons perched on a branch overhanging the river.  The earliest bridge at this spot was built in 1639, leading first to what was the West Farms neighborhood of New Haven until 1822, when the town of Orange was formed from the territory of New Haven west of the river. In 1921, Orange split into two towns, Orange to the north and West Haven to the south, the last of Connecticut’s 169 towns to be created.(1)  My first impressions are not positive: KFC, Penske/Firestone Tire Dealer, Dunkin Donuts, a car wash. Soon I reach a junction called Allingtown Green (they don’t use ‘Square’ much in Connecticut) where US 1 heads uphill, while Campbell Street heads south to West Haven Center. I have to make a decision: US1 has no sidewalks at all and is VERY narrow here as it heads sharply uphill, making it impossible to walk, but Campbell Street heads for what seems to be a very far off-course route to Milford, so I am not sure which road is the right road. Perhaps US 1 obliterated the original road or maybe the builders of the Milford Turnpike (which was the previous name for this road) straightened the old one, because there is no evidence at all of a winding road that might have been a precursor to the modern one. Also the hill is very steep as I mentioned earlier, very uncharacteristic of the old roads I have followed to date.  Plus, none of the diaries I have been following mention anything about steep hills on the way to Milford. But heading down Campbell Street also seems wrong as it appears to make a huge detour south through the center of West Haven.

        If only I had done a little local research before I embarked on my walk.  I have done this once or twice before, and it has never been a big problem but today it is a disaster. Whenever I am walking in a new area for which I have done little advance research I am always liable to take a wrong turn or head down the wrong street. I call this “outrunning my coverage” or sometimes “over-stretching my supply line,” like Napoleon in the infamous Winter Campaign in Russia in 1812. I decide initially that the level road is the sensible one so I start down Campbell Street. As I walk I impulsively change my mind and cut through the campus of the University of New Haven to reach the top of the hill, avoid the dangerous US 1 walk, and continue along US 1 at the top of the hill, where there is a sidewalk for a few yards. The view back to New Haven is quite nice from this elevation. I decide that this must be the way and continue on down the road. Pretty soon I start to have doubts as the road continues ahead in a dead straight line and cuts through an endless sea of commercial development.  I am constantly on the lookout for a promising side road or any evidence that this road predates its early nineteenth-century incarnation as the Milford Turnpike, but the absence of any sign at all makes me very nervous.  When I realize the road is still rising in elevation (226 feet high according to my iPhone elevation app at this point and still rising) I finally come to my senses and decide that Boston Post Road (US1) cannot possibly be the old road. I decide to cut my losses, and I turn away at the next left to find my way to the West Haven Library in the center of town to do some research before proceeding.

        A little research immediately proves the folly of altering my initial decision. Two separate sources point to Campbell Avenue as the main route from New Haven to Milford, passing through the center of West Haven.  I decide at this point that I should rename this project the “Main Street Project” because I am determined to not walk stretches like Boston Post Road in West Haven again; I would rather be wrong and enjoy the walk than be right and walk through a commercial wasteland. In the event I was right initially and should have ignored the direct road in favor of the more scenic route. Lesson learned. Except I make yet another mistake as the day progresses.

        I retrace my steps to Allingtown Green and follow Campbell Street about a mile into the center of West Haven, passing a Turkish Cultural Center and a Turkish restaurant called Saray from which nice smells emanate (no time to stop as I have a lot of walking to do still), as well as a Salvadoran restaurant, and continuing under the train tracks and Interstate 95.  West Haven Green is pleasant, and there is a nice multicultural mix in the city, although it is a slightly dogeared commercial center (perhaps because all the retail has moved to Boston Post Road).  I stop for lunch in the center of West Haven at a great diner called the Four Burritos, which is actually a Mexican restaurant disguised as a Greek Diner. I have a fantastic torta de carnitas, which is basically a grilled pork sandwich with avocado (trust me, it is out of this world. I don’t understand why tortas have not yet hit the mainstream like burritos here in the USA). A man named Louis sitting next to me tells me, apropos of nothing, that  the United States has never fought a war against a Catholic nation. I point out that Italy was part of the Axis during World War II, but Louis seems unimpressed with that fact. I think I see where he is going with this conversation when the discussion moves into whether Islam is a violent religion, so I start chatting with the waitress behind the counter to change the subject. She is a friendly young woman recently arrived from Ciudad Juarez, who pretends that my paltry Spanish is amazingly good (bless her), and the conversation drifts into a discussion of the high homicide rate in her hometown (Louis again!), so I decide to strike out for Milford at this point.

        West Haven Green is a large and pleasant park.  Main Street continues away from the Green as Route 162 and is a pleasant residential street dotted with the occasional eighteenth-century house, quite unlike the unremitting wasteland that lined Boston Post Road. After only a few minutes I reach another decision point as I arrive at a split where Main Street continues while Route 162 veers slightly south and becomes Platt Avenue and then Jones Hill Road which goes all the way to the Milford line. Lacking any historical evidence to help me, I decide that Jones Hill Road is the more likely and direct road so I start down Route 162 but change my mind after a couple of minutes and backtrack to follow West Main Street. Why? This time I reverse my initial instinct because I see what looks like a more low lying and winding route that follows Island Lane, which seems a better choice than the short but nevertheless hilly climb I have just embarked upon. Half an hour later, I pass the Ora Mason Branch of the West Haven Public Library and stop in to see what I can find out. I finally track down a book specifically about the history of West Haven from which I learn that my second-guessing has AGAIN been wrong! It turns out that Jones Hill Road was originally called THE KING’S HIGHWAY, and I have made the opposite mistake that I made this morning by looking for something too winding and complicated.(2)  Again, though, I should have trusted my initial instincts. 

        After returning to the original junction where I had followed the wrong road I start down what I hope is finally the original road to Milford. Soon I reach Jones Hill Road which, as you may have guessed, gradually climbs Jones Hill. The views of the area are quite nice from the higher points of the hill and a subsequent analysis of the topography indicates that the traveler had little choice but to cross over the hills west of New Haven en route to Milford. The decision seems to have come down to which was the easiest climb, and Jones Hill, the last high point before the ocean seems to have been the choice made by Indians and colonists.  At the corner of Jones Hill Road and Hubbard Road is what was clearly a colonial farmhouse, which confirms for me that this road existed in the colonial era, thus satisfying any lingering doubts I may have had about the choice of roads. Third time’s a charm they say. At four p.m. in the afternoon, as the sun starts to set over Long Island Sound, Jones Hill Road ends at the ocean, where the Oyster River flows into the sea. The Oyster River has marked the boundary between West Haven and Milford since 1674, and it is likely that this narrow and shallow tidal part of the river may have been easier to cross than points further upstream.

        Once I cross the bridge over the river I am in the Woodmont neighborhood of the town of Milford, and I have left West Haven after traversing many more roads in the town than I would have liked. But I eventually got it right and followed the road that George Washington mentions as the “lower road to West Haven” in 1789.(3) It should be noted that Washington took what he referred to as “the upper road to Milford, it being shorter than the lower one thru West Haven.”(4)  What this means is unclear to me as I can see no road that would qualify as a shorter road to the north of the King’s Highway except Boston Post Road, which did not exist at that time, at least not in the straight route it takes today. Perhaps he took the road to Derby and then the road from Derby to Milford which he thought was shorter or perhaps there is some evidence I am missing, but I am sure that in the colonial period (i.e. well before Washington’s 1789 trip) the road was called the King’s Highway, and that I am standing on it  here on Route 162, which in Milford is helpfully called New Haven Avenue. 

*****

        Washington actually did travel the “lower road through West Haven” on June 28, 1775, on his way to Boston to take command of the nascent Continental Army. A “Pilgrimage” on the route Washington took was undertaken by the Sons of the American Revolution in 1914, and the road he traveled was carefully researched by a local historian.(5)  Milford histories are more plentiful and discuss the road to New Haven in more detail than do the few books on West Haven. George H. Ford, in his Historical Sketches of Milford, states that “some roads were laid out on the Indian trails, such as the old road to New Haven by Burwell’s Farm and Oyster River.”(6) A map of Milford in 1874 shows the area then called Burwell’s Farm in the southeast corner of Milford, what today is called Woodmont. The road in 1874 is very much the same road as New Haven Avenue (Route 162) today, with a few of the bends and kinks removed from the original road.

        I follow New Haven Avenue through the Woodmont neighborhood as the sun begins to set. A short distance down the road I encounter a side street called King’s Highway, which heads straight for a few yards before ending at Chapel Street, which I turn right on to rejoin New Haven Avenue. At the junction of New Haven Avenue and Chapel Street is a red colonial house that has a Milford Preservation Trust sign on it, indicating it is old and that most likely the original road followed Chapel and King’s Highway. In other words, this little detour off New Haven Avenue is likely one of the “kinks” that got straightened out over the course of almost four centuries. As darkness starts to take over I reach a hill which is referred to in older histories as Eels Hill until I reach a heavily trafficked commercial area called Pond Point near the Indian River.  Old maps show the road that heads northeast here and is now called Gates Lane (although Lane is a misnomer today--this is a very busy road that leads to Interstate 95).  Perhaps that is the upper road that Washington took to New Haven fourteen years later.

        At this point it is completely dark but at least the way is clear because of the street lights, traffic, and lights from the abundant restaurants, shops, and gas stations that have now appeared as I approach the Indian River.  The Indian River is a wide river compared to the Oyster River Bridge. A bridge existed at this spot as early as 1662 when the Indian or Great River Bridge was built as the Indian River was “impassable at high tide.” (7) After crossing the bridge I find more bars, pizzerias, gas stations, florist shops, office buildings, a couple of modest apartment blocks with views of the estuary. At Buckingham Avenue I turn right (another ‘kink’ that was later straightened) which I follow for a few minutes, until it rejoins New Haven Avenue at the library. Darkness has set in, I have reached the center of Milford after a long day of wandering the wrong roads, and I want to make sure that does not happen again, so into the library I go for a few hours of research. As the Boy Scout motto says, “Be Prepared.”