Greenwood Road

United States Migration  Trails and Roads  Connecticut  Massachusetts  New York  Greenwood Road

Did an ancestor travel the Greenwood Road of Connecticut, Massachusetts, and New York? Learn about this settler migration route, its transportation history, and find related genealogy sources.

History
The Greenwood Road, also known as the Greenwoods Turnpike, was chartered by the Connecticut legislature in October 1798. In Massachusetts it was also called the Twelfth Massachusetts Turnpike chartered in 1801, and sometimes was locally called the Litchfield Turnpike. It connected to and became the Hudson Turnpike (aka Rensselaer and Columbia Turnpike) charging tolls from 1799 to 1896 in New York State bound for Albany. The Greenwood Road was one of the most heavily used roads to transport New England residents to Albany, New York, gateway to the Erie Canal.

The Greenwood Road route likely existed as a horse path, or no-charge wagon road prior to being chartered as a turnpike (toll roll). The Connecticut part of the turnpike was in operation (assessing tolls?) from 1799 to 1872. Railroads were faster, less expensive, and safer to use than overland wagon roads. As railroads entered an area, the long distance overland wagon roads (especially the toll roads) became less used. Railroads like these began moving settlers and replaced much of the wagon road traffic in the area:


 * 1831 Mohawk and Hudson Railroad (Albany, NY - Buffalo, NY)
 * 1833 Hartford and New Haven Railroad (Hartford, CT - New Haven, CT)
 * 1836 Albany and West Stockbridge Railroad (Albany, NY - West Stockbridge, MA)
 * 1836 Housatonic Railroad (Bridgeport, CT - Hudson and Berkshire Railroad)
 * 1838 Hudson and Berkshire Railroad (Hudson, NY - Housatonic Railroad)
 * 1841 Boston and Albany Railroad (Boston-Worcester-Sprinfield-Pittsfield-Albany)

Route
The Greenwood Road goes 111 miles (179 kilometers) from Hartford, Connecticut through North Canaan, Connecticut, then north into Massachusetts along the east side of the Housatonic River to Great Barrington, from there to Pittsfield, and then over the hills northwest into the corner of Columbia County, New York, and from there northwest to the city of Albany, New York.

Migrants who traveled the Greenwood Road route passed through these counties:


 * Hartford County, Connecticut
 * Litchfield County, Connecticut
 * Berkshire County, Massachusetts
 * Columbia County, New York
 * Rensselaer County, New York
 * Albany County, New York

Connecting Routes. The Greenwood Road connected with these additional migration routes:


 * Hartford, Connecticut connections:


 * Old Connecticut Path a pre-historic Indian path from Boston, Massachusetts to the Connecticut River Valley at Springfield, Massachusetts and south to Hartford, Connecticut.
 * The upper King's Highway, also known as the upper Boston Post Road, went from Boston to Springfield in Massachusetts, to Hartford and New Haven in Connecticut, and then on to New York City. From Boston to Hartford it followed the same route as the Old Connecticut Path. From New York City the King's Highway continued south to Charleston, South Carolina.


 * Mid-road Massachusetts/Connecticut connections:


 * Catskill Road from Springfield, Massachusetts to Ancram, New York to Catskill, New York and the Catskill Turnpike from Catskill to Unadilla, New York and beyond. The Catskill Road (north) crossed the Greenwood Road at Great Barrington, Massachusetts. The Catskill Road (south) crossed the Greenwood Road at North Canaan, Connecticut.


 * Albany, New York connections:


 * Albany Post Road from New York City to Albany, New York
 * Mohawk or Iroquois Trail from Boston, Massachusetts to Albany to Fort Oswego, New York
 * Erie Canal from Albany to Buffalo, New York
 * Champlain Canal from Albany to Lake Champlain between New York and Vermont

Modern parallels. The modern roads that roughly match the Greenwood Road route from Hartford, Connecticut to Albany, New York are:


 * U.S. Route 44 Hartford, CT to North Canaan, CT
 * U.S. Route 7 North Canaan, CT to Pittsfield, MA
 * U.S. Route 20 Pittsfield, MA to Albany, NY

Settler Records
No list is known to exist of migrating citizens who used the Greenwood Road and decided to settle along it. However, many of the earliest settlers in the area would have used this road to reach their new home. The Greenwood Road would have attracted nearby settlers because it helped them reach markets for buying and selling goods and services. Therefore, the land records, tax records, and histories of the earliest settlers along the route would list the names of people likely to have used the Greenwood Road.

Settlers along the Greenwood Road are most likely to have originally come from Connecticut or Massachusetts.