Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Building Bridges in Boston, or How to Lose Friends and Money.

Charlestown Bridge, the contemporary successor to the original bridge at the mouth of the Charles River, seen from the Charlestown side. The first bridge was built in 1786, 156 years after the settlement of towns of Charlestown and Boston; prior to this a ferry carried passengers across the river.

“One if by land, and two if by sea:

And I on the opposite shore shall be.”

The Midnight Ride of Paul Revere, Henry Wadsworth Longfellow. First published in The Atlantic Monthly in 1861 .

“We returned from Cambridge by way of Charlestown. Crossing that ferry to Boston…”

Dr. Alexander Hamilton, Entry Wednesday, August 15, 1744 in Gentleman’s Progress, p.142.

Thus far in this project I have written twenty essays on walks I have taken in Boston. However, with the exception of a brief foray into Harvard Square along JFK Street after walking across the Anderson Memorial Bridge (the modern successor of the original bridge across the river from what is now Allston to Cambridge), I have spent little time on the other side of the Charles River. Charlestown, an important town of its own in colonial Massachusetts and today a neighborhood of Boston, is located directly across the Charles River from Boston. Two other important towns in the Colonial era, Cambridge and Watertown, which have been mentioned in previous entries but have not been discussed in detail, are also located on the north bank of the Charles River and thus also require passage across the river.

The Charlestown Bridge, at the mouth of the Charles River as it empties into Boston Harbor, is the first of many bridges across the river that blueback herring and alewives pass under on their annual spring journey up to their freshwater spawning sites. Yet, until 1786, the first bridge across the river encountered by these anadromous species of fish was the aforementioned Cambridge Bridge (now the Anderson Bridge), five miles upriver from the Charlestown Bridge. I need to cross the Charlestown Bridge in order to follow the last of the old roads leading out of Boston which are the subject of this series of essays. This main road in and out of the town of Boston in the Colonial era deviated from the road previously discussed which crossed the river at the bridge in what is now Watertown Square to Newton, Brighton, Brookline, and Roxbury. Instead of crossing the bridge at Watertown, this alternate road continued on the same side of the river through Watertown to Harvard Square, then across Cambridge, through what is now Somerville, and then traveled the length of the Charlestown peninsula before reaching the mouth of the Charles River directly across from the North End of Boston. From this point a ferry was required to cross over to the town of Boston until the end of the eighteenth century when a bridge was finally built to connect Boston directly with its neighbors on the opposite side of the river. Subsequently many more bridges were built until crossing the river, once a tedious endeavor, became something hardly noticed by a modern traveler.

However, the astonishing fact that for over one hundred and fifty years, two small bridges located five miles and nine miles upriver from Boston Harbor provided the sole crossing points to the important towns of Cambridge and Watertown across the Charles River lured me to investigate the history and development of the various bridges that cross the river from the bridge to Charlestown up the river to the crossing at Watertown, where one of the previous entries ended.

Detail of Bonner Map of Boston (1722) showing the site of the ferry crossing to Charlestown from Boston, located at the end of Prince Street in the North End.  Bonner conveniently includes a drawing of a ferry boat with passengers being rowed across the river. Also note Gee’s Shipyard adjacent to Ferry Way, mentioned below as a putative location for a bridge as early as 1712.


From my vantage point at the foot of the Charlestown Bridge near the North End of Boston it is barely a third of a mile to the first settlement of John Winthrop and the Puritans just across the river in Charlestown. This short distance across the Charles River which separates Charlestown, Cambridge, and Watertown from Boston appears to be inconsequentially small and yet it proved a major obstacle to travel and thus to development and even to warfare as we shall see. In fact, the earliest roads were built precisely to minimize topographical complications such as large steep hills and even more importantly in the context of the current discussion, to make river crossings as simple as possible. Hence, the importance for two centuries of the bridge over the Charles at Watertown, the first place a boat traveling upriver would encounter a waterfall requiring portage, and also the first reasonably narrow distance between the banks of the river to build a simple bridge.

From today’s City Square, the historic center of Charlestown just across the bridge from the North End of Boston, it is about a mile to the Old State House and about 7.1 miles to Watertown Square following the old roads through Charlestown, Somerville, and Cambridge. Thus a walk from the Old State House in Boston to Watertown via the Charlestown Bridge is about three quarters of a mile shorter (8.2 miles) than a walk along the route to Watertown I have described in previous entries (down Washington Street through Roxbury, Brookline, Brighton, and Newton Corner, a total of 9.0 miles). Only there was no bridge to Charlestown until June 17, 1786, when the first bridge at the mouth of the Charles River was opened, beginning a process of land filling and bridge building which dramatically transformed the topography and development of the compact town on the Shawmut peninsula.

James Birket, in his Some Cursory Remarks, an account of a voyage to North America in 1750-1, writes that on September 7, 1750 he “Dined with Jacob Ryall Esquire in company with Henry Vassels and in the evening went with said Vassels to Cambridge in his chase being 8 miles the land way but over Charlestown ferry tis only recon’d 4 miles (page 17)” an early record of the notion that a bridge would make life easier for people wishing to travel between Boston and points north.

The absence of a bridge was also noted by Thomas Anburey, a British lieutenant serving under the command of General John Burgoyne, during his period of captivity in Cambridge following the surrender of the army at the Battle of Saratoga in October 1777. In a letter dated December 9, 1777, Anburey records:

“Opposite to the northern part of the peninsula on which Boston stands, are the remains of Charlestown, which had the same connection with Boston as the Borough has with the city of London; the river that divides the two is not much wider than the Thames, and it appears rather singular, that the inhabitants never erected a bridge, as it would have greatly contributed to the prosperity of both, especially as it was the direct entrance from the inland towns into Boston. Unless you cross the ferry, you have to make a circuit of several miles, over swamps and morasses, from this place to Boston, which is only two miles in a direct line; no doubt, as the Americans are become so expert in making bridges across rivers of greater width than this, they will, when the contest is ended, erect one; for what was formerly either through indolence or individual concerns considered as impossibilities and arduous undertakings, will now be thought matters easily accomplished.”

Indeed, the absence of a bridge directly resulted in two of the most famous events associated with the American Revolution in Boston. The first of these was of course the famous ride of Paul Revere and the equally famous lanterns discussed in Longfellow’s well-known poem. Revere was one of the riders assigned to warn the citizens of Lexington of the impending arrival of troops sent by the Royal Governor Thomas Gage on the night of April 18, 1775. The troops had two options to reach Lexington, also on the north side of the Charles River: travel the aforementioned long and winding road “over swamps and morasses”, or cross the river by boat to a point in Cambridge and continue on foot. The soldiers were ferried across the river. Revere, as one of the messengers, awaited a signal from lanterns hung in the North Church steeple in the North End, which would be visible across the river in Charlestown, where Revere was conveniently located, having surreptitiously rowed across the river earlier in the evening.  Once the two lanterns were hung, Revere could then ride his horse along the road out of Charlestown and warn of the impending arrival of the troops. The rest, as they say, is history.

The second event affected by the absence of a bridge was the Battle of Bunker Hill, which took place just above Charlestown on June 17, 1775. On the previous evening colonial forces under the command of William Prescott occupied the high ground above Charlestown, which offered a clear view of the mouth of the Charles River, and put the harbor and Boston within range of colonial artillery. As mentioned countless times in these entries, Boston was located on a peninsula with only one way out by land along the road to Roxbury. Colonial forces had already seized the high ground in Roxbury preventing British forces from traveling the road out. Now, with forces occupying the high ground in Charlestown, the army was forced to send troops across the water or be subject to bombardment and be forced to evacuate the town of Boston. Thus the first major battle of the American Revolution was fought in Charlestown, resulting in a pyrrhic victory for the Royal troops: they managed to seize control of the hill but with massive casualties, which gave the colonial troops much-needed confidence in their fighting ability. As a result of the damage done at the battle of Bunker Hill, when General Washington’s troops placed artillery on top of Dorchester Heights to the south of Boston in March 1776, also putting both the town and the harbor within striking distance, the choice was clear and the British army evacuated the town of Boston. The war was over in Boston, and the lack of a bridge across the river from Boston played a major role in the outcome.


From New York Magazine, September 1795. Found opposite page 19 in Hunnewell’s History of Charlestown (1888). Based upon an image published in Massachusetts Magazine, September, 1789.


As Anburey predicted, a bridge was built across the Charles River from Boston to Charlestown shortly after the conclusion of the Revolutionary War. And it seems he was accurate too about the engineering acumen of the American bridge builders. As another visitor, Jacques-Pierre Brissot de Warville noted in his New Travels in the United States of America in 1788, “The greatest monuments to the industry of the state are the three bridges at Charles, Malden, and Essex (p. 107),” a reference to three bridges across rivers (The Charles, Mystic, and Danvers River) north of Boston recently constructed. Later, visiting Charlestown, Brissot de Warville states “you arrive at Bunker Hill by the superb bridge at Charleston [Note: Charlestown is frequently and confusingly spelled in the manner above in in the eighteenth century], of which I have previously spoken. This town was entirely burnt by the English in their attack of Bunker Hill. It is at present rebuilt with elegant houses of wood (p. 121).” Even George Washington had high praise for the newly constructed bridge across the mouth of the Charles River. In his diary of the trip made to New England as President of the United States, Washington records on October 29, 1789, that he “Passed over the Bridge at Charles-Town,” which he extols as “useful and noble—doing great credit to the enterprising spirit of the People of this State. (p.38)”

What took so long? There was certainly interest in a bridge for many years. A ferry had been established as early as 1630, when at a Court of Assistants, Nov. 9, 1630, it was ordered “ that whosoever shall first give in his name to Mr. Governor that he will undertake to set up a ferry betwixt Boston and Charlestown, and shall begin the same at such time as Mr. Governor shall appoint, shall have one penny for every person, and one penny for every hundred weight of goods he shall so transport.” (Memorial History of Boston, Volume I, pp.227-8). Apparently a man named Edward Converse was the first to give in his name as he was licensed to run the ferry in 1631 (Memorial History of Boston, Volume I, p. 393.)  In November, 1637, “the Governor and Treasurer were authorized to lease the ferry for the term of three years at the rate of £40 per annum; and at the expiration of that time it was granted to the college.” (Memorial History, Vol. I, pp227-8). Thus, in what seems to be an early example of ‘rent-seeking’, the license was conveyed to Harvard College, who continued to employ a ferryman but recovered most of the profit. As we shall see, the Harvard deal did not go quietly into the night when the Charlestown Bridge was built.

Map of Boston by Osgood Carleton likely from 1805 (not 1803 as shown at bottom). At the top of the map is the Charlestown Bridge, opened in 1786. To the left is the West Boston Bridge, opened in 1793. At bottom right is the South Boston Bridge, opened in 1805. Also shown is a proposed second bridge to South Boston. Also about to be built roughly at the R in Charles at top left is the Craigie Bridge, opened in 1809.

According to Henry Edes in his chapter on the history of Charlestown in the provincial period in The Memorial History of Boston, (Volume II, p324) “As early as 1712, it was proposed to build a bridge ‘at the place where the Ferry is now kept; viz., from below Mr. Gee’s [Note: Gee’s is shown on the map above] and Hudson’s Point to the landing place on this side.’ This was to be a private enterprise, encouraged and sustained by a proper toll, authorized by the General Court. The project was renewed in 1720, and again in 1738. In the last-named year it was proposed to establish a ferry, or to build a bridge, from ” the Copper Works ” in the westerly part of Boston to the farm of the Hon. Spencer Phips in Cambridge. This town was opposed to both plans.” According to an early chronicler of Boston history, Thomas Pemberton, Governor Thomas Hutchinson, last colonial Governor of Massachusetts Bay Colony thought the project a “Quixote enterprise” (cited in Whitehill, p. 255).

Finally, in 1785, a group of investors, including John Hancock put up £15,000 to build a bridge 1503 feet in length, over a river “wider and deeper than the Thames at London” and the impact was immediate. Not only was there a large celebration, but the success of the bridge prompted immediate speculation about the construction of additional bridges to connect Boston more directly with its various hinterlands across the water. A second bridge was opened to Cambridge from the west end of Cambridge Street in Boston in 1793. This ‘West Boston Bridge’ (now the Longfellow Bridge) resulted in the rapid development of both the West End of Boston and East Cambridge. The distance from Boston to Harvard Square was reduced from eight miles to a little over three miles. In 1805 a bridge to South Boston was opened and in 1809 a third bridge across the Charles, The Craigie Bridge (now the Charles River Dam Bridge), was built. The transformation of Boston from an isolated town on the Shawmut peninsula to the “Hub of the Universe’ had begun.

Milestone in Cambridge near Cambridge Common, reading “Boston 8 miles 1734 AI” AI stands for Alexander Ireland, a surveyor. This distance indicated the circuitous route required to get to Downtown Boston, a trip of 3.4 miles today.

Obverse side of milestone at left with an update from 1794, reading “Cambridge New Bridge 2 1/4 miles 1794.” The ‘New Bridge’ is the West Boston Bridge, the contemporary version being the Longfellow Bridge over which the Red Line Train travels.




Building bridges is a common term for bringing people together. However the history of bridge construction in Boston is one of acrimony, political battles, greed, and anger.  From the earliest days building bridges was guaranteed to start conflicts between and among the townspeople of Boston and other towns on the Charles River. The first bridge across the Charles River, first opened in 1641, was the aforementioned bridge across the river at Watertown Square, a “footbridge over Charles River at the head of tide-water, very near the first mill, usually called Mill Bridge, or the Great Bridge.” (Drake, Middlesex County, Vol. I, p.426). This bridge was an instant source of tension in Watertown as well as other towns affected by it. Who was responsible for upkeep, Watertown alone or other towns benefiting from the use of the bridge? Who would repair the bridge when, as frequently happened, it was pulled down by currents, winds, ice and snow, or wear and tear from hooves, feet, and carts crossing? These and many other controversies plagued the various versions of the Watertown bridge from the start.

A few years later, in 1662, a second bridge was built from Allston to Cambridge at roughly the location of today’s Anderson Memorial Bridge which also resulted in bitter disputes over upkeep. As we have seen in the case of Allston and Brighton, disputes over this bridge and a proposed new bridge led to the secession of Brighton (along with what became Allston) from Cambridge. No wonder these two bridges were the sole crossing points for the first ten miles upriver for so long.

As mentioned earlier, there was long-standing strong opposition to the construction of the Charlestown Bridge. However, once built, coupled with the burgeoning population of Boston, the bridge opened the floodgates as it were to more construction and eventually to the filling of the Back Bay. The relationship between Boston and Cambridge is completely different today compared to the relative isolation of the two towns in the colonial era, and the impetus for the topographical  transformation of the land bordering the Charles River can be traced to the early flush of engineering enterprise at the opening of the river into Boston Harbor.

However, the story has a more complicated ending than the somewhat uplifting tale of the progressive spirit of the young Republic unshackled from the bonds of royal servitude. Enter Harvard University, an institution that seems to hover over most events in the history of Boston like a dark masonic force. Harvard, the reader may recall, was given the rights to the ferry across the river. The government continued to modify the rules governing ferries and Harvard benefited from near monopoly status on the transport of passengers from Boston to Charlestown. In 1641, for example the Court passed a general order regulating the use of ferries, and providing that every person to whom a ferry was granted should have “the sole liberty of transporting passengers from the place where such ferry is granted to any other ferry, or place where ferry-boats used to land, and that any ferry-boat that shall land passengers at any other ferry may not take passengers from thence, if the ferry-boat of the place be ready; provided that this order shall not prejudice the liberty of any that do use to pass in their own or neighbors’ canoes or boats to their ordinary labors or business” (Memorial History, I, 228.)

It should come as no surprise that Harvard was none too pleased about the loss of revenue resulting from the construction of the Charlestown Bridge. Thus, although the investors each stumped up £100 for a share in the bridge, “The company was empowered to collect tolls (which were to be doubled on the Lord’s Day) for a term of forty years, on condition of paying two hundred pounds annually to Harvard College, to compensate that institution for the loss of the ferriage between Boston and Charlestown. Subsequently the right to take tolls was extended for thirty years, on account of the charter granted for the building of the West Boston Bridge; but the double Sunday toll was abolished. ” (Memorial History, Vol IV, 26-7.)

Not only were the investors annoyed at this unmerited redistribution of profits, travelers across the bridge were not happy about the tolls, particularly the obnoxious doubling of the rate on Sundays. The subsequent bridges were also toll bridges until in 1828, under strong pressure from voters, Mayor Josiah Quincy authorized construction of the Warren Bridge, a free bridge across the river to Charlestown. Finally it was possible to walk freely to Charlestown from Boston.

The story does not end here either, and once again Harvard and the largely Harvard-affiliated investors in the Charlestown Bridge were the primary source of friction. The investors in the Charlestown Bridge Company sued the state of Massachusetts and the Warren Bridge Company, arguing that they had received a monopoly from the state and that the authorization of a new bridge, particularly a ‘free’ bridge was illegal and would hurt their profits. In what became a landmark case in the Supreme Court, Charles River Bridge v. Warren Bridge (1837), A majority of justices led by Chief Justice Roger B. Taney delivered a verdict favorable to the Warren Bridge, arguing that the state had a right to promote the well-being of the citizens, and indeed were obligated not to give up “any portion of that power over their own internal police and improvement, which is so necessary to their well-being and prosperity.” (cited in Howe, What God Hath Wrought, p. 443) In other words, the needs of the community were of greater import to the state than the rights of a company to a profit, especially if the profits of the company are an impediment to progress.

The effect was immediate: “Soon after that time the draw of Charles River Bridge was permanently raised, and the use of the highway was discontinued. In 1840 the State bought the franchise and property for $30,000, and re-established tolls for the purpose of keeping the two Charlestown bridges in repair. They both afterward passed into the hands of the municipalities of Boston and Charlestown jointly, and are now free highways maintained by Boston alone.” (Memorial History, Vol. IV, 27.) Today the site of the Warren Bridge, taken down in 1962, is occupied by the New Charles River Dam built in 1978 to replace the old dam at Lechmere. It is a pleasant experience to cross the dam over the locks, occasionally being halted by the passage of a boat through one of the locks. For two years I made the trip across the locks daily when I worked at the Charlestown Navy Yard, but that is a story for another entry.

The history of infrastructure development in Boston and in America is filled with similar tales of infrastructure improvements leading to monopolistic power, followed by rampant speculation leading to large scale over-building in an effort to cash in, soon followed by financial failure and the intervention of the state to maintain the bridges or turnpikes which failed to make the anticipated riches for the zealous investors. Charlestown Bridge and the preceding ferry proved to be a cash cow until speculative pressure as well as public disenchantment with high costs forced the hand of the market and ultimately the government. Surely there is a lesson in this story about the most useful way in which to build infrastructure. One certainty is that building bridges is guaranteed to not build bridges between people.


Below is a list of the principal bridges across the Charles River in order of their initial construction. Most have been rebuilt several times over the years. Note: the list does not include the numerous rail bridges except when they are part of a multipurpose bridge such as the Longfellow Bridge. Also does not include on ramps or off ramps of highways, such as the Leverett Connector.

Earliest Bridge- Watertown (1641) Current bridge (1907)

Second bridge- Cambridge (1662) Current bridge is the Anderson Memorial Bridge (1915)

Third bridge- Charlestown (1786) Harvard allowed £200 a year to replace income lost from ferry (1631). Current bridge (1900) Free of Charge! Appropriately, this is also the ‘Freedom Trail’ bridge.

Fourth Bridge- West End Bridge (1793) Current bridge Longfellow Bridge (1906)

Craigie Bridge (1809) (Lechmere Bridge, Middlesex Canal Bridge, Old Charles River Dam Bridge)

River Street Bridge (1810) New bridge (1925) replaced the one from Brighton discussed in previous entry. This bridge caused Brighton to become an independent town from Cambridge.

Mill Dam (1821) Now Beacon Street, but originally a bridge. The beginning of the creation of the Back Bay neighborhood.

Arsenal Street Bridge (1824) replaced 1925. A bridge built as a direct consequence of the establishment of a turnpike to more directly connect Boston and Watertown.

Warren Bridge (1828) (demolished 1962, replaced by Charles River Dam 1978)  built as a result of protests at tolls on Charlestown Bridge.

Boston University Bridge- 1850s drawbridge (replaced 1928)

North Beacon Street Bridge (1917) but must be earlier as there is a bridge at the site on an 1852 map. further investigation required.

Harvard Bridge (1891)  i.e Mass. Ave Bridge, rebuilt several times

Western Avenue Bridge (1924) the actual site of the original River Street bridge

Weeks Footbridge (1927). Probably the closest thing to the original Watertown Bridge of 1641.

Eliot Bridge (1950). Named for Charles Eliot, noted landscape architect and a founder of the Trustees of Reservations and his father Charles Eliot, president of Harvard.

Charlestown High Bridge (1956)- Zakim Bridge from 2004 replaced bridge from 1956 i.e. Interstate-93 North bridge.



Walter Muir Whitehill, Boston: A Topographical History, 2nd edition. Cambridge, Belknap Press, 1968.

Thomas Anburey, Travels through the Interior Parts of America by Thomas Anburey, lieutenant in the army of General Burgoyne; with a foreward by Major-General William Harding Carter. Boston, Houghton Mifflin, 1923.

Samuel Adams Drake, History of Middlesex County, two volumes. Boston, Estes and Lauriat, 1880.

The Memorial History of Boston, including Suffolk County, 1630-1880. Four Volumes. Justin Windsor, Editor. Boston, Osgood & Co., 1882.

Daniel Walker Howe, What God Hath Wrought: The Transformation of America, 1815-1848. New York: Oxford University Press, 2007.

Special thanks to Dr. Dana Comi for reviewing this manuscript and pointing me towards the Taney ruling of 1837.

2 Responses to Building Bridges in Boston, or How to Lose Friends and Money.

  1. […] difference between the earliest route and the distance between these two points today reflects the building of bridges across the Charles River. The West Boston Bridge (now the Longfellow Bridge) for example, which was […]

  2. […] the distance to Boston from the west by two miles, as I have discussed in previous entries (and this one). I am in the process of creating a map that color codes every mile from Boston along the old roads […]


Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes:
<a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>