The Catskill Road, also known as the Catskill Turnpike, also known as the Ancram Turnpike, was one of the most important early routes for migration out of New England into central New York. It was used by European settlers as early as 1744. It was about a 100 mile (161 kilometer) pathway from Springfield, Massachusetts to Catskill, New York, via Ancram, New York. The route went westward from Springfield, Massachusetts toward the southwest corner of that state. It entered New York State near the town of Ancram and went thence northwest to the town of Catskill on the west bank of the Hudson River. From Catskill the highway was usually called the Catskill Turnpike and hugged the north edge of the Catskill Mountains running toward Unadilla (formerly Wattle's Ferry) on the Susquehanna River, and beyond to Ithaca and Bath, New York.
The first major village began attracting European settlers into the Catskill area in 1745.
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. The establishment of the stagecoach inn in Ancram, New York, in 1798 shows stagecoaches traveled the Catskill Road even before it was made a turnpike. The inn was popular with drovers taking their cattle to the Hudson River for market.
Toll roads. 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 Catskill Turnpike was a gateway route into central New York when it opened from Catskill to Unadilla in 1804. Moreover, New York, Connecticut, and Massachusetts all approved an important network of feeder turnpike routes leading toward the Catskill Turnpike—which eventually became associated with the Catskill name.
Railroad competition. The heyday of wagon roads into central New York was the early 1800s before the coming of the railroads in the 1840s and 1850s. 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)
There may have been several variations of the Catskill Road. New York State historical roadside markers show Ancram was connected by old turnpikes both to (a) Barrington, Massachusetts via Hillsdale (Nobletown), New York, and to (b) Salisbury, Connecticut. Therefore, immigrants from Springfield could have chosen two main routes of similar length to arrive at Catskill:
Hampden County, Massachusetts
Hampden County, Massachusetts
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 Catskill Road connected with several other migration routes:
- Springfield 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:
- mid-road New York connection:
- Catskill connection:
Modern parallels. The modern roads that roughly match the Catskill Road (southern route) from Springfield to Catskill are:
- From Springfield, Massachusetts cross the Connecticut River into Agawam, and take MA‑147 / Memorial Avenue going southwest 1.6 miles until it merges into
- Southwick Street /MA-57 heading west for 37.1 miles to New Marlboro; turn south onto
- New Marlboro Southfield Road bound toward Southfield 5.6 miles to turn right onto
- the Canaan Southfield Road to Canaan, Connecticut. At Canaan turn west on
- Church Street / US-44 W head southwest to Millerton, New York; there turn northwest on
- N Elm Ave / NY-22 which eventually becomes NY-82 going past Livingston until it joins
- NY-23 / Claverack Road west bound over the Hudson River bridge into Catskill, New York.
No list is known to exist of migrating citizens who used the Catskill Road or Catskill Turnpike 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 Catskill 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 Catskill Road.
Settlers along the Catskill Road are most likely to have originally come from Massachusetts or Connecticut, especially areas near Springfield, Boston, or Hartford.
- Handybook for Genealogists: United States of America, 9th ed. (Logan, Utah: Everton Pub., 1999), pages 532 and M-48. At various libraries (WorldCat); FHL Book 973 D27e 1999. This was one of the most important migration routes for early New England settlers who pioneered into central New York.
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- 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.
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- Wood, 363-64.
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