Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Dedham, Massachusetts. Mile 10: Trials and Tribulations (WTPR#12)

Norfolk County Courthouse, Dedham, Massachusetts

“He told me that this place was the most sharping country ever I was in and that this little piddling trick was only the beginning of it and nothing to what I should experience if I stayed there but some weeks.”1Dr. Alexander Hamilton, Gentleman’s Progress: The Itinerarium of Dr. Alexander Hamilton, 1744. edited with an introduction by Carl Bridenbaugh. (Pittsburgh: University of Pittsburgh Press, 1948), 105-106. This is one of my favorite books, a diary kept by a doctor from Annapolis Maryland who traveled to New England for his health in 1744.

Dr. Alexander Hamilton, in Gentleman’s Progress, p.105, describing his encounter with a bar maid who “secret(ed) one of our lemons” in Ames Tavern, Dedham, Massachusetts, Wednesday July 18, 1744.


This is entry #12 from my previous project, Walking the Post Road. I have been slowly transferring the entries over to this project for a number of reasons. The first reason is that they are relevant to this project in that the first dozen or so are ‘rambles’ about Boston. Even the entries that are not about Boston are about the Boston Post Road. Indeed, writing about places outside of Boston gives me a fresh perspective which is useful when I am writing about Boston. The main reason, however, is that the previous project was done on Apple’s iweb, which is no longer supported by Apple and, consequently, the website is slowly decaying. I will eventually revisit that project and bring the entire site up to date. In the meantime readers are welcome to comment upon this entry as part of this project. It has been updated and edited slightly from the original version which was published on Friday, June 11, 2010, as entry #12, Mile 10.


As a teenager, my image of Dedham, Massachusetts was colored by my limited interactions with the town and its inhabitants. I occasionally went to the Dedham Mall, a monstrously ugly collection of big box stores on busy Route 1, which I reached from my house in Braintree via Route 128, the major highway circumnavigating Boston. I played on the high school tennis team, and although Braintree High School had a mediocre team, we were guaranteed to beat the crap out of the awful Dedham High School team, even accounting for their ability to use their terrible, cracked, and run-down courts to their advantage (they knew which direction the ball would go when it hit certain seams in the court). I played a church team from Dedham in a CYO basketball league once, and the kids on that team were such thugs that we got into a fistfight with them as soon as the game was over. In short, I thought Dedham was a complete dump full of white trash and jerks, which seems to also have been the opinion of Dr. Alexander Hamilton in 1744 (see above quotation).

        Imagine my surprise when I entered Dedham Centre for the first time on foot and discovered an amazingly well-kept New England village squirreled away behind the highways and the strip malls that seem to be the only Dedham one sees from a car. Beautiful old houses line elegant squares. Old church buildings are everywhere, and the elegant Norfolk County Courthouse is only the most impressive of a series of lovely buildings on High Street. The Dedham Public Library and the Dedham Historical Society are also housed in stately buildings, there is an old community movie theater, and there is even a beautiful old former prison building that has been converted into an apartment building. I was completely taken aback and pleasantly surprised to discover this hidden gem; then I discovered that Dedham has a deep and rich historical past and has had a significant role to play in the development of the Post Road, and I became even more interested in the town.

The Post Road in Dedham dies out at a brook at the end of Lower East Street, but I rediscover it on the other side of the brook, as a short street called Eastbrook Road. The original road continues across Washington Street (The former Dedham Turnpike) and becomes East Street. Looking over the fence and through the trees at Mother Brook, part of a man-made canal from the 1640s to connect the Charles River to the Neponset River in Dedham. The change in height of the water from the Charles to the slightly lower Neponset provided suitable power to operate mills along the Brook for centuries.


As I enter Dedham from Boston on Centre Street in West Roxbury, my first inauspicious observations do nothing to alter my preconceived notions about the town. The street name changes to Lower East Street, but one would be hard pressed to know that without a map as the street signs are conspicuously absent, as are sidewalks in stretches here. Shortly I arrive at what appears to be a dead end as the road peters out into some bushes. Peering through them I see a small brook meandering across the route. There is a road that leads left off East Street, and in a few yards I arrive at busy, wide, straight Washington Street, which, as I mentioned in a previous post, was originally built in the early 1800s as the Dedham Turnpike to shorten the distance from Boston to points south. I am forced to follow this road a few hundred yards, and it is an unpleasant experience compounded by the massive road construction project being undertaken at the moment. I am already beginning to miss the anodyne but quiet street I had been following until just a few minutes ago. On my right looms the gigantic parking lot and collection of the world’s worst mall architecture called the Dedham Mall. Just before I begin to despair of the entire endeavor I spot a small sign, which reads Eastbrook Road and leads to the right and down a small incline. I follow this “road” a few yards until it reaches a dead-end at a small white fence just in front of some trees. I look through the trees and discover the same brook– only I have reached the opposite side and am looking back. Eureka! This must have been the original route, there must have been a bridge over the brook, and this road must have fallen into disrepair at some point and been bypassed in favor of Washington Street. I quickly scramble back up the incline and look around for the continuation of the road which I see up ahead about one hundred yards on the left-hand side of Washington Street. I cross Washington Street with some difficulty as there are no crosswalks, and cars and trucks are flying by at breakneck speed, and make my way over to East Street, where I turn left, pass a cemetery and enter a tranquil, boring, and somewhat ugly residential neighborhood. Now I am deeply appreciative about this circumstance after the experience I have just undergone.  I continue walking for about half a mile and come to an intersection with High Street, Dedham and the first difficult decision concerning the route of the Post Road I have faced on my brief adventure thus far.

Update April 22, 2022. The little fence in front of the site of the old bridge over Mother Brook is gone, the little creek that ran into the brook has been put underground and the site is quite ugly these days as can be seen in the photo below left. The construction project along Washington Street has finished but it is still very busy and full of traffic and unpleasant to walk along. However, it is now possible to see the old Post Road across the Dedham Turnpike (Washington Street) sloping downwards toward Mother Brook.

View across Washington Street, formerly the Dedham Turnpike, to the remannt of the original road from Boston to Dedham. Today Eastbrook Road, which formerly crossed Mother Brook to become East Street, is a dead end
Same place in April 2022 as the photo above with the white fence. Progress?
Detail from Hales’ 1831 map of Dedham, showing the area walked in this entry. The Dedham Turnpike is today’s Washington Street (the Dedham Mall is basically the area immediately above the word ‘Dedham’). As can be seen on the map above, the original road to Dedham before 1800 and the arrival of the turnpike once crossed Mother Brook and then crossed the turnpike. This is the road that comes in from the right above the ‘Ro’ of Roxbury and above the ‘turnpike’. Mother Brook leads from the Charles River down the map, eventually linking up with the Neponset River. After crossing Mother Brook and the Dedham Turnpike, the old Post Road, today called East Street, continues into Dedham Center (it is the curving road under the word Dedham running just beneath the turnpike) until it reaches High Street. The junction at East and High Street is the point where the two possible Post Roads to Providence diverge. The entries for these two separate walks through Dedham will be transferred to this website soon. The walk described in this entry continued into Dedham Center along High Street, ending at the Courthouse, which is shown on the map at top left.
A beautiful sight– East Street sign post indicates I have rediscovered the Post Road after a short but harrowing adventure on busy Washington Street in Dedham, near the Dedham Mall.


As I make my way into Dedham center away from the noise, traffic, and general ugliness of the Washington Street, Dedham Mall, Route 1 conglomeration, I smile when I think that the town was originally proposed for settlement in 1635 as the town of Contentment.2Robert B. Hanson, Building Dedham: 350 Years of History, 1636-1986. (Dedham Historical Society, 1986, p. 3.) The original land grant comprised 177 square miles, which eventually became sixteen towns, leaving the town today with only 11 square miles. The town of Dedham was officially established in 1636 and was one of the earliest towns not directly on the ocean. The history and settlement of Dedham is, however, linked directly to water: the town is bordered by two major watershed rivers, the Charles on the west and the Neponset on the east.3 Erastus Worthington, The History of Dedham, From the Beginning of Its Settlement in September, 1635 to May 1827 (Boston: Dutton and Wentworth, 1827), Chapter 1, passim. The earliest English-built canal in America was constructed to connect the two rivers, the flow from the higher to the slightly lower river providing the energy to power mills. This canal was called the Mother Brook and is the very brook that I encountered earlier.4Hanson, p. 26.

The down side of following the exact route of the old road. Construction on Washington Street near the Dedham Mall.

Another body of water, Dwight’s Brook, ran across East Street where I stand now. A bridge was built in 1637 called Dwight’s Causeway, and this bridge provided an easy and direct connection to Boston unless the brook overflowed, which happened to another of my fellow travelers, Madam Sarah Kemble Knight, who traveled the Post Road from Boston to New Haven and back in 1703/4 on horseback, accompanied only by local guides. Her very interesting diary recounting her journey is one of the earliest travel accounts in North America and is much more in the spirit of Paul Theroux than the pollyanna style of Rick Steves. Her account of her attempt to get back to Boston on March 2, 1704 is a great example of her writing style:

     “Wee were now in the colony of Massachusetts and taking lodgings at the first Inn we had come to had a pretty difficult passage the next day which was the Second of March by reason of the sloughy ways then thawed by the Sunn.

    “Missing my way in going up a very steep Hill, my horse dropt down under me as Dead: this new surprise no little hurt me meeting it just at the Entrance into Dedham from whence we intended to reach home that night. But now was obliged to get another Hors there and leave my own, resolving for Boston that night if possible. But in going over the Causeway at Dedham the bridge being overflowed by the high waters coming down I very narrowly escaped falling over into the river Hors and all wch twas almost a miracle I did not- now it grew late in the afternoon and the people having very much discouraged us about the sloughy way wch they said wee should find very difficult and hazardous it so wrought on mee being tired and dispirited and disappointed of my desires of going home that I agreed to Lodge there that night wch wee did at the house of one Draper, and the next day being March 3d wee got safe home to Boston.5Sarah Kemble Knight, The Journal of Madam Knight in Colonial American Travel Narratives, edited by Wendy Martin (New York: Penguin Books, 1994), p. 53.

Tranquil Dedham Common, the town originally called Contentment when it was settled in 1635.

The Draper she refers to ran a tavern in West Roxbury. We met the father of the tavern keeper in my last entry at the Westerly Burying Ground. Madam Knight also visited the tavern in Dedham that another of my fellow travelers visited in 1744, and her experience was not much more enthusiastic than Alexander Hamilton’s (He is not the Hamilton you probably are thinking of. I will spend a lot of time describing his journey in future entries.)  Knight had arrived in Dedham to “meet ye Western Post. Post didn’t show so I resolved to go to Billingses where he used (usually) to lodg, being twelve miles further.” She goes to the tavern to get a guide but finds it difficult as “they, being tyed by the Lipps to a pewter engine” were unhelpful.6 Ibid, p. 53. In other words, she had gone to Dedham to meet up with the Postal Rider in order to have a guide to accompany her. Having missed him, she went to the tavern to find another guide but she had difficulty finding help because everyone was busy drinking.

A reproduction of the famous tavern sign created by Nathaniel Ames, mocking the legal abilities of Chief Justice Paul Dudley (at center with back turned).

            Taverns served many functions in colonial New England. They were, first and foremost, drinking and eating establishments, but they also served as inns, post offices, courthouses (Samuel Sewall often held his court sessions in the local tavern), places to change horses, and as centers of news or gossip.7 David Conroy, In Public Houses: Drink and the Revolution of Authority in Colonial Massachusetts (Chapel Hill: UNC Press, 1995),13. The tavern in Dedham, for much of it’s early history, was originally run by Joshua Fisher, who in 1658 was allowed “to sell strong waters to relieve the inhabitants, being remote from Boston…”8 Robert B. Hanson, Dedham, Massachusetts, 1635-1890 (Dedham Historical Society, 1976), 122. After his death in 1709 the tavern passed into the hands of his son, also Joshua Fisher, who ran it until his death in 1730, at which time his widow Hannah and her four daughters took control. One of the daughters, Mary Fisher, married Nathaniel Ames in 1735, and he became involved in running the tavern, until his wife died giving birth to a son, Fisher Ames, who also died. At this point Ames remarried a cousin of Mary’s and relinquished the tavern back to Hannah Fisher, who died in 1744. Another daughter married Benjamin Gay, who took over the running of the tavern. However Ames sued for the rights to the tavern under the complicated claim that his dead son Fisher should be the rightful heir, and thus Nathaniel Ames inherited the tavern. The case became quite well known and, after many twists and turns, reached the Superior Court of Massachusetts in 1749, where a majority of the justices decided in favor of Ames. Ames proceeded to create a complicated tavern sign consisting of the Superior Court Justices grouped around a table studying an open book called “Province Law.” However two of the Justices, have their backs turned to the law book. One of the Justices is clearly Chief Justice Paul Dudley, who sided with Gay in the case. Paul Dudley, you may recall, is discussed in some detail in WTPR entry #6.  Ames eventually passed the almanac and the tavern on to his son Nathaniel who left the tavern to his mother who remarried,and the tavern became known as Woodward’s tavern until its demise in the early nineteenth century.

       Nathaniel Ames was perhaps more famous as a writer of an almanac. Almanacs in the colonial era served many purposes, one of which was to describe the roads the traveler might encounter in a journey to unknown parts. In particular almanacs often listed the names of taverns and the distances from one tavern to the next. Thomas Prince, minister of Old South Meeting House, published an almanac called Vade Mecum for America in 1732 in which he provides, among other things, a chart with all the taverns between Boston and Jamestown, Virginia along the Post Road, with the town in which they are located and the distance between each tavern as well as the total distance from the Boston to each tavern. The first two entries are for Shippey’s tavern in Roxbury, two miles from Boston Town House, and Fisher’s tavern in Dedham, nine miles from Shippey’s and eleven miles from Boston. This almanac will be an invaluable guide to me on my travels.9Thomas Prince, Vade Mecum for America, or a Companion for Travelers and Traders (Boston: Kneeland & Green for D. Henchman and T. Hancock, 1731, in Evans #3470), p. 199.


   Fisher/Ames/Woodward’s  Tavern was at the junction of High and Court Streets in Dedham Center, a few hundred yards away from East Street. In the 1790s Norfolk County was created out of all the towns in Suffolk County except Boston and Chelsea, and Dedham was chosen as the shire town. Thus a courthouse was built across the street from what by then was called Woodward’s tavern. This courthouse was replaced a century later by a much larger, more ornate courthouse which remains today. One of the most famous trials in the history of the United States occurred at the Norfolk County Courthouse in the 1920s. Two Italian men, Nicola Sacco and Bartolomeo Vanzetti, were accused of robbing a shoe factory in Braintree and murdering two of the employees in 1920. Convicted of armed robbery and murder, the two men were electrocuted on August 23, 1927 amid vociferous international protests at what was perceived by many to be an unfair trial against two men who were convicted not because of the robbery and murder but because they were Italian and Anarchists. To this day arguments persist over whether the two men were guilty of the crime and whether, even if they were guilty, the trials were fair.


        The original Post Road originally passed to the east of the center of town. However, at some point in the mid-eighteenth century, High Street to Court Street to Highland Street became the preferred route. I will discuss these changes and other changes to the main route of the Post Road in the next and future entries. My problem is which way to go? Do I continue along the road via East Street or do I follow the newer route from the 1750s via Court and Highland Street? Both are valid, one is older and as we shall see, there are even more possibilities as one road branched off west to Medfield and on to Connecticut, the so-called Middle Post Road. There are many “Post Roads,” and it will be difficult to decide which route is the best.

        For now I will settle into one of the cafes in Dedham and relax in “Contentment.” After a pleasant walk around the quiet neighborhoods I will take in a movie at the Dedham Community Theater and then grab some dinner at one of the pleasant restaurants in town. Tomorrow is another day, and I can leave the decision to another day and then head back out on the road or roads. I will keep an eye on my waitress though, as I have been warned she might try to steal my lemons.   

1795 painting of Dedham, courtesy of Dedham Historical Society. The Fisher (Ames, and by this time Woodward) tavern is adjacent to the white building at center left, which is the new court house built in 1793 when Dedham became the shire town of the newly created Norfolk County. The road in the foreground is Highland Street, the Post Road at the time of the painting since about 1760, when it was rerouted from East Street, the original road to Narragansett Bay. At top in this entry is the current Norfolk County courthouse, located directly across the street from the original courthouse. The newer building above was the scene of the infamous Sacco and Vanzetti trial in the 1920s.

Distance Traveled in this entry: 1.0 miles

Total Distance traveled for this project: 11.0 miles

2022 update: There is a reason I am publishing this entry after publishing the entries on Watertown. Both towns are sufficiently removed from Boston (Colonial Boston, basically today’s Downtown) that a traveler in the eighteenth century would be inclined to stop here as Adams and our spies Browne and DeBerniere did in Watertown (or in the case of Brewer’s Tavern, just over the line in Waltham). Watertown and Dedham were two focal points for the two main roads to New York from Boston: the Lower Post Road for Dedham, and the Upper Post Road in the case of Watertown. Both are about 10-11 miles out of town along the old roads and there are numerous narratives that mention each place and their taverns. Thus there is a symmetry between the the new entries I am writing about the Upper Post Road and the corresponding entry from the walk along the Lower Post Road and the entries I wrote about in 2010 that I am transferring here. I will try to keep this symmetric alternating pattern of newer Upper Post Road and older updated Lower Post Road entries going on this website. WTPR #X in the title represents the older entries while UPBR #X represents the newer entries for anyone who wants to follow the walks in sequence rather than jump back and forth in time like Dr. Who (that analogy is for you Cheryl!).

High Street in Dedham looking East from Court Street, showing the Registry of Deeds, the District Court, and the former Christian Science Church. The registry is the site of the Ames (Woodward/Fisher) Tavern mentioned in the text.

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