Canton Historical Society
Once Ragged Row
Pleasant Street is one of the oldest streets in the Town and one which the residents have preferred to keep winding and picturesque rather than widening it and losing many lovely old trees. A history of the street appears in Huntoons account and the following quotation gives the flavor of the past, when there were few houses in Canton and horses carried residents over roads that were often just cart-paths.
''Halfway up the Meeting-House Hill we cross the Taunton Old Way, and are now at the beginning of Pleasant Street. This street, from Washington Street to Reservoir Pond, was not laid out until 1723; it is described as running from the northerly end of the dam still standing on Pequit Brook, then called Hartwell's Dam on the east side of the old fence that stood between the land of John Wentworth and Jabez Searle, thence to Washington St. This road connected at what in 1760 was known as Bussey's Corner with the road to Dorchester Swamp. From this point in very early days, a cart-path, marked by blazed trees, meandered alternately on both sides of this present street. It was used to bring timber and shingles from the swamps in Stoughton to the landing-place at Milton. This early way, I believe, led to Stoughton through Pine Street, and was known in 1730 as the way to Nathaniel Stearns's. Huntoon believed the cart-path was the one described in Judge Sewall's diary on the date of Sept. 24, 1709, when the judge writes that he leaves "Morey's at Ponkapog and goes over the new road" without seeing a house in a stretch of 14 miles. The cart-path is also shown on Butchers map, dated 1698.
The road to Dorchester swamp, with which the 1723 road connected, was laid out in 1719-20 and followed very closely the present route of Pleasant Street to Stoughton.
By 1798 Pleasant Street led to the spot known as Withington's Corner. Huntoon writes, "From its tortuous and irregular windings, and shabby, desolate houses, it acquired, the nickname of Ragged Row. The map of 1830 calls it the Stoughton Road."
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