To understand the importance of transportation to the economy of Boston, one need only look at the history of the West End. In colonial time ropewalks, mills which made rope for sailing vessels, were quite prevalent throughout West Boston. As the economy of New England shifted from maritime to industrial, the hand dug 27-mile Middlesex Canal (1803) carried goods from New Hampshire and Lowell to a terminus in the West End. This mode of transport was later pushed aside by the Boston & Lowell Railroad (1835) and the many other rail lines which sprouted up around the newly filled Mill Pond.

The first iteration of the MBTA, Boston’s public transportation system, started in Bowdoin Square with the horse-drawn Cambridge Railroad. The company was chartered and incorporated in 1853; opening the line from Bowdoin Square to Harvard Square sometime after 1856. It was later purchased, consolidated and renamed the West End Street Railway.

1676 Edward Randolph writes of Boston:

“It is the great care of the merchants to keep their ships in constant employ, which makes them trye all ports to force a trade, whereby they abound with all sorts of commodities, and Boston may be esteemed the mart town of the West Indies”

The Ropewalk
“In that building, long and low,
With its windows all a-row
Like the port-holes of a hulk,
Human spiders spin and spin,
Backwards down their thread so thin
Dropping, each a hempen thread…”
– Henry W. Longfellow (1854)


Ropewalk etching

1722 Captain Bonner’s map of Boston shows wooden buildings (ropewalks), which made marine cordage with tar and hemp. They were unfortunately severe fire hazard and their proclivity to burn necessitated the need to locate these peninsular appendages in sparsely populated or swampy areas.

1747 A town petition refers to shipbuilding as “the ancient and almost only manufacture the town of Boston ever had”

1748 The port of Boston is extremely busy, with 540 vessels leaving and 430 entering, not counting coasting or fishing vessels.

1786 Construction of West End Bridges across the Charles River start to connect Boston with towns north: Charles River Bridge (Charlestown Bridge), West Boston Bridge (Longfellow Bridge), Canal Bridge (Craigie Bridge) and the Warren Bridge (demolished)

1785 The Charles River Bridge (a toll bridge) was the first bridge chartered on this site and was opened on June 17, 1786.

1792 The West Boston Bridge (a toll bridge) was constructed in 1793, connecting West Boston to Cambridge.

1794 There were fourteen ropewalks in Boston.

1807 The Canal Bridge (a toll bridge) was named after the Middlesex Canal. The bridge was opened in 1809, and came to be known as Craigie’s Bridge.

1828 The Warren Bridge was chartered in in a location extremely close to the Charles River Bridge, the investors filed a lawsuit which eventually reached the United States Supreme Court as Charles River Bridge v. Warren Bridge. The Warren Bridge was requested in 1823 and chartered in 1828 by John Skinner and Isaac Warren, in response to the politically unpopular tolls on the 1786 Charles River Bridge.

Middlesex Canal

Middlesex Canal

1803 Middlesex Canal built.

1807 December. President Thomas Jefferson’s Embargo Act goes into effect. Since more than 1/3 of British imports pass through the Port of Boston, the law hurts the town financially. Some Boston merchants petition the president to end the Embargo; others ignore the law.

1835 The Boston and Lowell Railroad was one of the first railroads in North America and the first major one in Massachusetts. The line later operated as part of the Boston and Maine Railroad’s Southern Division.

1845 The Boston and Maine Railroad (B&M) until 1964, was the dominant railroad of the northern New England region of the United States for a century. It is now part of the Pan Am Railways network.

1848 The Fitchburg Railroad was a former railroad company, which built a railroad line across northern Massachusetts, leading to and through the Hoosac Tunnel. The Fitchburg was leased to the Boston and Maine Railroad in 1900. The main line from Boston to Fitchburg is now operated as the MBTA Fitchburg Line.
1852 The Eastern Railroad connected Boston, Massachusetts, to Portland, Maine. Throughout its history, it competed with the Boston and Maine Railroad for service between those two cities, until the Boston & Maine finally put an end to the competition by leasing the Eastern in December 1884.

1856 The Cambridge Railroad was the first street railway in the Boston, Massachusetts area, linking Harvard Square in Cambridge to Cambridge Street and Grove Street in Boston’s West End, via Massachusetts Avenue, Main Street and the West Boston Bridge.

Cambridge Railroad at Bowdoin Square

Cambridge Railroad at Bowdoin Square