Dorchester Avenue

Road patterns set in early times still influence life today.  The starting point for the story of Dorchester Avenue goes back to colonial times.

As you can see from the 1788 map of Boston, there was only one land connection between Boston and the mainland and one bridge to Charlestown.  Notice Nook’s Hill, outlined in red.

No. 21930 Detail from the 1788 map of Boston

There was no corresponding bridge to the south, so travelers and freight including produce from the farms of Brookline, Dorchester and Roxbury all converged onto what is now Washington Street.  At that time the road ran along a narrow neck of land connecting Boston to Roxbury.  Although there were wharves along the Boston side of the South Bay, Dorchester Neck (South Boston) was sparsely settled during the Colonial period.  In the 17th century South Boston had been Dorchester’s cow pasture, where the herds foraged during the day. (Columbia Point was the calf pasture).

In 1804, Dorchester Neck was taken from Dorchester to create South Boston. This did not include the area around Andrew Square, but the Andrew Square or Washington Village part of Dorchester was later annexed to Boston in the 1850s.

In 1804, at the same the state legislature approved the annexation of South Boston, they authorized a toll bridge to link South Boston to Boston.  The bridge was about a block south of what is now the Broadway Bridge.  On the Boston side, the bridge was called the Dover Street Bridge and on the South Boston side, it was called the Bridge at West Fourth Street.

This 1803 map shows the proposed bridge, outlined here in red.  The vertical line of a proposed bridge at the end of what would become Dorchester Avenue was not built until 1826. It was called the North Free Bridge and is in approximately the same location as the Dorchester Avenue Bridge or overpass near Gillette Shavings headquarters today.   The area between the edge of land at the left and South Boston on the right was a channel of water and tidal mudflats.

No. 14907 South Boston Bridge 1805

In comparison, this map shows the current configuration with a huge area of land made by bringing in fill from outside the city.

No. 21949 Modern map showing location of former South Boston Bridge

21931 Modern map showing comparison of made land in the area of the South Boston Bridge

While the bridge was under construction in 1804-1805, a proposition for a turnpike to lead from it toward points south was brought forth, and in consequence the Dorchester Turnpike Corporation was created by act of the legislature on March 4, 1805, with a franchise to build a road from the bridge over the Neponset River at Lower Mills, commonly called Milton Bridge, to Nook Point, in Boston.

This was the era of Turnpike construction.    “In nearly every case the road was finally given up as an almost total loss.”   They became public roads in the middle of the century.. and we will see that the Dorchester Turnpike did indeed become Dorchester Avenue.

At Milton Lower Mills, the road connected to Adams Street for travel to points south and, except for a short intervening distance, its terminus was not far from the Blue Hill Turnpike, leading south on an inland route, which offered a direct and improved road all the way to Taunton. Taunton was foremost in the production of brick and iron as well as a shipping port.

This was the era of Turnpike construction.

The road costs were more than anticipated, which obliged the corporation to charge higher tolls, making the road unpopular. Many people preferred to go a longer route through Roxbury without the toll. Returns show that this was one of the best paying of the turnpikes. Receipts began to climb in 1826 and reached a peak in 1838, when the gross earnings were fourteen percent and the net earnings were nine percent. Earnings dropped immediately upon the opening of the Old Colony Railroad in 1844.

The Dorchester Turnpike was laid out as a public way April 22, 1854 by public subscription and was then named Dorchester Avenue. In 1856 the name was changed to Federal Street, but Dorchester Avenue was restored in 1870.

Two years after the Corporation relinquished its control, horse cars appeared on the new public street.

No. 14622 Photograph of first street card service by horse-drawn street car. This scene was probably in South Boston.

This map from 1876 shows the horse railway routes active at that time, highlighted with blue lines.  The red lines are steam railroads.

No. 21899 detail from 1876 map of horse railroads, indicated with blue lines.  There was a horse railroad route along Dorchester Avenue.

20307 Detail from 1831 Baker map of Dorchester.  The very nearly straight road that enters the map at the to right and travels diagonally toward the bottom is Dorchester Avenue.

The following is from “The Dorchester and Roxbury Street Railroad.” Louis P. Hager. History of the West End Street Railway In Which is Included Sketches of the Early Street Railways of Boston. (Boston, 1892), 14, 18-19.

This was in 1852, and the corporators named were William D. Swan, Charles C. Holbrook and William Hendry. By a special act passed May 30, 1857, they were empowered “to construct, maintain and use a railway or railways, with convenient single or double tracks, from a point on Meeting House Hill, in the town of Dorchester, upon and over Hancock and Stoughton streets, so called, in said town of Dorchester, to the line separating said town from the city of Roxbury ; and also from a point near the Town House in said Dorchester, upon and over Washington street, so called in said town, to the line separating said town from the city of Roxbury, and at said line to connect with the Metropolitan Railroad Company,” etc. The duration of this corporation was extended by the Legislature, but on October 1, 1864, its property and franchise passed into the hands of the Metropolitan Railroad Company.

Dorchester Railway

The Dorchester Railway Company succeeded the Dorchester Avenue Railway Company in January, 1858, by decree of the supreme judicial court, the company failing to meet the provisions of its charter, which was granted in 1854. Its corporators were Cheever Newhall, Edward King and John J. May, the first location granted being “from a point near the Lower Mills, so called, in the town of Dorchester, upon and over the way or street heretofore known by the name of the Dorchester turnpike, or Turnpike street,

to the line of the city of Boston, and thence upon and over such’ streets in South Boston as the Board of Aldermen of the city of Boston may determine, upon and over the North Free bridge (Federal street bridge), and upon and over Sea and Broad streets in the direction of State street.” All subsequent locations were granted the Dorchester Railway as successors of the Dorchester Avenue Railway Company. It is related of the latter organization that it was equipped at one period of its brief existence with double-deck

cars, and that after passing through a series of discouraging annoyances by its competitors, met its death by an accident to four of its passengers, who purposely tumbled from the top of the car on which they were riding and then sued the company for damages. Judgment was rendered against the corporation, and this with other unfortunate circumstances caused its collapse. As stated elsewhere, the property and franchise of the Dorchester Railway Company passed into the hands of the Metropolitan Railroad  Company, October 1, 1863.

Dorchester Extension Railway

Henry L. Pierce, Asaph Churchill and Edward H. R, Ruggles were the corporators of this company, which received its charter February 18, 1859. Its line was located from a point near the Lower Mills in Dorchester, and connected with the (then) terminus of the Dorchester Railway at Centre street in that town. This road was purchased by the Metropolitan Railroad Company in October, 1863, and the several locations thereafter were granted the latter corporation.

PDF1199 Old Dorchester South Boston Turnpike by Lawrence Berry parts one and two

PDF1199 Lawrence Berry. “Old Dorchester South Boston Turnpike.”

PDF1038 Sammarco Former Dorchester Turnpike Jan1997

PDF1038 Anthony Sammarco. “Foremer “Dorchester Turnpike” had rich, vibrant history.”


Orcutt, William Dana. Good Old Dorchester: A Narrative History of the Town, 1630-1893. (Cambridge, 1893).

Wood, Frederic J. The Turnpikes of New England. (Pepperell, MA: Branch Line Press, 1997. Originally published in 1919).

Louis P. Hager. History of the West End Street Railway In Which is Included Sketches of the Early Street Railways of Boston. (Boston, 1892)


Posted on

December 31, 2021

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