The first public thoroughfare used by the settlers of Windsor in 1633 was an Indian trail between Plymouth Meadow (behind today’s Loomis Chaffee School) and the head of Hartford Meadow near the present village of Wilson. At first it was a simple footpath and was later widened for use by cart and horse. When Wethersfield and Hartford were settled in 1634 and 1635, respectively, and communication opened between “The Three River Towns,” the road way was continued from Wilson south through Hartford Meadow and on to Wethersfield.
The first reference to the present Route 159 from Broad Street to Hartford is dated 1638 when the General Court at Hartford voted that a public highway for cart and horse be built upon the upland between Hartford and Windsor. This change occurred because the old Indian trial went right through the only planting ground fit for cultivation by the Hartford settlers and everyone traveling across their lots was a nuisance. Evidently nothing happened, and in 1640 it was again voted to establish this upland road. However, travelers continued to pass through the cultivated meadows belonging to citizens of Hartford. In 1645 it was once again brought before the Court that travel along this Indian trail be stopped and Windsor and Hartford were to see to the building of a new upland road. This last order seems to have been followed, and a very crooked road around all of the swamps was laid out. Deerfield Road is evidence of this crooked layout.
Bowfield was the ancient name applied to the land west of the present Broad Street green. The early settlers’ lots had run from there down to the Rivulet (Farmington River). Not knowing that this land was prone to flooding, they built their original house at the foot of the ridge near the old Island Road. In 1639 an exceptionally bad flood destroyed all of their homes. They then built on the higher ground behind their barns (just west of the present railroad tracks near the Town Hall, post office, and Huntington House), and this later became part of the upland road. The upland road in Windsor Center later became Broad Street. The section south of Stony Hill became Windsor Avenue. The record of the opening of Broad Street and the definition of the upland road is not dated but must have taken place sometime in the 1650s or early 1660s. These highways remained dirt or gravel until 1896 when the Connecticut State Highway Department put a macadam pavement on one section. Every year another section was macadamized until by 1914 the existing highway was finished with concrete, bituminous and brick pavement, from the Hartford city line to Poquonock Avenue (Route 75).
In 1757 a faction of the Congregational church split off and built Windsor’s third meeting house on upper Broad Street, parallel to Palisado Avenue. In 1792 the two groups agreed to reunite if an academy was built south of the Rivulet and a new meetinghouse (now the fourth) was built north of the river with a bridge and causeway connecting the two. Thus came the present bridge location and causeway leading to the First Church in Windsor and Palisado Avenue.
Island Road, coming north from Plymouth Meadow, became what was later called Rowland Lane. This road continued across the Rivulet beyond the Palisado Common (today’s Palisado Green) about two miles. There, Hayden Station Road (known as “Pink Street” until the late 1940s) now branches off to the west. When Northampton, Massachusetts, was settled in the 1650s, a direct route north became necessary. This road was opened across what was called “the plains” in present day Windsor Locks and Suffield. This northern route was the main thoroughfare and mail route north until about 1820. It was originally referred to as the “Old Country Road“ and later the upper route of the “Boston Post Road.”
A road heading north from the intersection of Hayden Station Road wasn’t opened until 1815. This road had been delayed for years because of the many bridges necessary for crossing swamps, whereas the road through the plains was mostly sandy and flat.
While we complain of roads and traffic today, imagine what it was like to travel in Windsor in the 1600s and 1700s. Mud might swallow half of a large, wooden wagon wheel but early travelers were at least spared our modern problems of gridlocked traffic and road rage.
By Bev Garvan, historian, 2002