The Greenwood Road, also known as the Greenwoods Turnpike, connected Hartford, Connecticut to Albany, New York on a 111 mile (179 kilometer) route. 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.
Albany on the Hudson River was settled in 1614 by colonists from the Netherlands. The Dutch also settled close to Hartford in 1623 but abandoned that outpost in 1654. Hartford on the Connecticut River was founded in 1635 by Puritans from Boston, Massachusetts, who were formerly from England. To connect these two colonies Indian footpaths were apparently expanded into horse paths, and later widened further into wagon roads.
Stages. Stagecoaches generally began regular transport of mail and passengers on long trips in the American colonies in the 1760s. They made regular trips between stages or stations where travelers were provided food and rest. Where available, stagecoaches became a preferred way for settlers to travel to a new home.
Tolls. As traffic increased along a roadway American political leaders turned to toll roads (turnpikes) to raise money to improve, clear, and repair their local highways. Toll revenue from stagecoaches, drovers, and other travelers was used to maintain the roadbeds and bridges, and, if there was enough left over (rarely happened), to pay a turnpike stockholder dividend. If turnpike revenue decreased too much, the roadway maintenance was typically turned over to the state and the path was made a free public road.
The Greenwoods Turnpike was chartered by the Connecticut legislature in October 1798. It was open as a toll road from 1799 to 1872. In Massachusetts it was also called the Twelfth Massachusetts Turnpike chartered in 1801, and was a toll road until 1857. Sometimes it 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. 
Railroad competition. 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) normally became less used. Railroads like the following 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)
The Greenwood Road originally went 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
New York main routes west moving New Englanders into central New York (listed north to south)
- Erie Canal from Albany, NY to Buffalo, NY; opened 1825.
- Mohawk or Iroquois Trail from Albany, NY to Fort Oswego, NY; opened 1722.  
- Catskill Turnpike (aka Susquehannah Turnpike ) from Catskill, NY to Unadilla, NY; route travelled by Europeans by 1792; toll booths opened by 1804.   
- New York feeders from Massachusetts / Connecticut connected to NY main routes west
- Rensselaer and Columbia Turnpike from Massachusetts 10th Turnpike at New Lebanon, NY (Pittsfield, MA) to Rensselaer, NY (Albany, NY); opened 1799; now US-20.
- Hillsdale and Chatham Turnpike from the Alford and Egremont Turnpike at Alford, MA to Albany, NY; opened 1805. 
- Columbia Turnpike from the Massachusetts 12th Turnpike and Great Barrington and Alford Turnpike at Hillsdale, NY (Egremont, MA) to Hudson, NY (Catskill, NY); opened 1799; now NY-23.
- Ancram Turnpike from the Salisbury and Canaan Turnpike at Millerton, NY to Catskill, NY; opened 1805; now NY-82.
- Ulster and Delaware Turnpike from the Salisbury and Canaan Turnpike at Millerton, NY (Salisbury, CT) to Rhinebeck, NY (Kingston, NY), continuing west to the Catskill Turnpike at Bainbridge, NY; opened 1802; now NY-199. 
- Massachusetts feeders connected to New York feeders
- Massachusetts 10th Turnpike from Connecticut Turnpike at Sandisfield, MA to the Rensselaer and Columbia Turnpike at Hancock, MA (New Lebanon, NY); toll booths open 1800 to 1854; now US-202 and US-20.
- Housatonic River Turnpike from the Massachusetts 10th Turnpike to the Rensselaer and Columbia Turnpike at West Strockbridge, MA (Hillsdale, NY); toll booths open 1809 to 1853; now in part MA-102.
- Alford and Egremont Turnpike from the Massachusetts 12th Turnpike at Egremont, MA to the Hillsdale and Chatham Turnpike at Alford, MA (Hillsdale, NY); toll booths open 1812 to 1842; now MA-71.
- Great Barrington and Alford Turnpike from the Massachusetts 15th Turnpike at Great Barrington, MA to the Columbia Turnpike at Alford, MA (Hillsdale, NY); toll booths open from 1812 to 1846; now MA-23.
- Massachusetts 12th Turnpike from Sheffied, MA (North Canaan, CT) to the Columbia Turnpike at Egremont, MA (Hillsdale, NY); toll booths open from 1803 to 1857; now US-7 and MA-41.
- Hampden and Berkshire Turnpike from near Springfield, MA to the Becket Turnpike at Becket, MA; toll booths open from 1829 to 1852; now I-90.
- Connecticut feeders connected to New York feeders
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:
Modern parallels. The modern roads that roughly match the Greenwood Road route from Hartford, Connecticut to Albany, New York are:
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.
- The Greenwood Road (map)
- Greenwood Road in Routes in the Northeast United States in RootsWeb (accessed 5 October 2014).
- Greenwoods Turnpike
- List of Connecticut turnpikes
- Albany, New York in Wikipedia: the Free Encyclopedia (accessed 30 October 2014).
- Hartford, Connecticut in Wikipedia: the Free Encyclopedia (accessed 30 October 2014).
- Frederic J. Wood, "The Twelfth Massachusetts Turnpike" in The Turnpikes of New England and the Evolution of the Same Through England, Virginia, and Maryland (Boston: Marshall Jones, 1919), 26-27. Internet Archive version online.
- Stagecoach in Wikipedia: the Free Encyclopedia (accessed 30 October 2014).
- Wood, 33-36.
- List of turnpikes in Connecticut in Wikipedia: the Free Encyclopedia (accessed 24 October 2014).
- US 44 Turnpikes in Connecticut Roads (accessed 24 October 2014).
- Wood, 79-80.
- Wood, 79-80.
- U.S. Route 20 in New York in Wikipedia: the Free Encyclopedia (accessed 30 October 2014).
- Wikipedia contributors, "Erie Canal" in Wikipedia: The Free Encyclopedia at http://en.wikipedia.org/wiki/Erie_Canal (accessed 24 June 2009).
- Handybook for Genealogists: United States of America, 10th ed. (Draper, Utah: Everton Pub., 2002), 851. WorldCat entry. FHL Book 973 D27e 2002.
- Wikipedia contributors, "Fort Oswego" in Wikipedia: the Free Encyclopedia at http://en.wikipedia.org/wiki/Fort_Oswego (accessed 2 July 2011).
- Mohawk Trail in Routes in the Northeastern United States: Historic Trail, Roads, and Migration Routes in RootsWeb (accessed 6 October 2014).
- List of turnpikes in New York in Wikipedia: the Free Encyclopedia (accessed 1 November 2014).
- Almira E Morgan, The Catskill Turnpike: A Wilderness Path (Ithaca, N.Y.: DeWitt Historical Society of Thompkins County, 1971). Online digital copy.
- Anastassia Zinke, The Susquehanna Turnpike and America's Frontier History in Catskill Mountain Foundation (accessed 1 November 2014).
- Joan Odess, The Susquehanna Turnpike (pdf accessed 1 November 2014).
- Wood, 168.
- Isaac Huntting, History of the Little Nine Partners of North East Precinct and Pine Plains, New York, Dutchess County (Amenia, NY: Chas. Walsh, 1897), 99-101. Google Book edition
- Wood, map between pages 56 and 57, and pages 76-78.
- Wood, map between pages 56 and 57, and pages 166-67.
- Wood, map between pages 56 and 57, and page 168.
- Wood, map between pages 56 and 57, and pages 186-87.
- Wood, map between pages 56 and 57, and page 80.
- Wood, 203-206.
- Wood, 363-64.
- Connectiuct Route 126 in Wikipedia: the Free Encyclopedia (accessed 3 November 2014).
- "Salisbury and Canaan Turnpike" in Routes in the Northeastern United States: Historic Trails, Roads, and Migration Routes in RootsWeb (accessed 3 November 2014).