The town of Greenwood was formed from Troupsburgh and Canisteo, Jan. 24, 1827. West Union was taken from it in 1845, and a part of Jasper was annexed in 1848. It lies upon the western border of the county, and is bounded north by Hartsville, east by Jasper, south by West Union, and west by the county line. Bennett’s Creek runs through the east part of the town through a valley excavated from four to six hundred feet below the hill-tops. The central and western part of the town is rolling upland of clayey loam, and the valleys being loam mixed with gravel and shale.

Alexander H. Stephens came up Bennett’s Creek from Canisteo, in company with Anson Robinson, popularly known as "Robinson Crusoe," and commenced the first clearing in the town of Greenwood, a mile north of the present village, on the Hovey Stephens place, in the spring of 1821.Ezra Cobey, a Prussian had previously made a small clearing three miles down the creek, in Canisteo. The road had been chopped up through the valley and south to the State line, by the land-office, but was not cleared. They worked here during the summer and part of the winter, living in a log cabin and working on their mill, Mrs. John Stephens coming up occasionally to do their cooking. The family did not move into Greenwood until the mill was running. Ezra and John H. Stephens moved up the valley first, and Phineas came soon after. The mill, to which soon added to "run" of stones, was built near the Brundage mill, and run by an undershot breast-wheel. The outlines of the old pond are still marked by willows. This was the first mill built in the town, and was operated by Uriah Stephens until 1825, when Colonel John Stephens moved into the town. At this time there was no mill in reach of the settlements down the creek nearer than at Wombough’s, on the Tuscarora, and another north, on the Canisteo.

Settlement along the creek was made very fast after the mill was built.

Deacon Jacob Manning, from New Hampshire, came in 1823, his family consisting of his wife and one son, Daniel Manning. Dennis Sanford settled back on the hill towards Krusin’s Corners, in 1824. Eleazer Woodward came in 1823, from New Hampshire, and opened a tannery on a small stream to the east, near the mill. Sebe Norton and Stephen Powell settled in the southwest part of the town, on a ridge, and Enoch Ordway and his two sons-in-law, "Hoose" Carr and Ezra Lovejoy, Hiram Putnam, John H. Hoyt, Joseph and Josephus Bachelor, and Jacob Manning settled along and near the creek. Guy Wardwell lived on the strip of land annexed to Greenwood from Jasper before any other settlement was made in the town. Next to building a mill, the opening of a tavern and crossroads was an alluring enterprise.

In the fall of 1824, Levi Davis, of Dryden, Tompkins Co., ame and bought the site of the present village of Greenwood, built a log house, and in March, 1825, moved in and opened a tavern. In one corner of the room a bar was fenced off, and in which he sold goods, which consisted mainly of tea, snuff, cotton cloth, tobacco, port, and whiskey (worth twenty cents a gallon at the still), oats, hay, and indigo for coloring cloth. This was the first tavern and store in the town. As business increased, he added a bedroom to the front stoop, and built a kitchen in the rear. Mr. Davis also commenced the manufacture of pot and pearl ashes, which he continued for thirty years. The farmers when clearing their land gathered and saved the ashes, which they boiled down in bad weather, selling the black ash at the store. Seven hundred bushels of ashes were required for a ton of potash, which would be worth from $80 to &100. A man could make $10 a month by gathering his ashes and boiling down the proceeds. This was a cash business, the Liverpool market readily absorbing these chemicals, until the Russians entered into the competition some years later. The first post office in the town was at this store. Joshua L. Chapman, then a boy of fifteen, carried the mails on horseback throught the dense forest from Hornellsville to Canisteo, passing through Greenwood, the journey taking him one day each way. This was in 1828-29. In 1826, Col. Ira Davenport, father of Hon. Ira Davenport, the present State senator, became Mr. Davis’ partner. David Foote and Wm. Ferguson, who bought two village lots of Redmond Davis, a short distance above the store, and opened a coffin and furniture factory in 1830, were the next settlers

in the future village. Some of their heavy carved work is still treasured by Mr. Davis, as specimens of artistic skill.

In 1830, Benjamin F. Brundage moved from Bath, and erected a carding and cloth-dressing factory in Greenwood, in which he did a successful business until its destruction by fire in 1846, when it was replaced by the present flouring-mill. Mr. Brundage has been a prominent citizen. Of his seven sons, Robert L. and Benjamin C. are prominent lawyers; Israel M. a successful farmer, --he has for several years been supervisor of the town; and John M. Brundage has been justice of sessions.

Daniel McCormick came from the county of Antrim in 1832, and built a grist-mill at Rough and Ready. In 1834 his brother James came, bringing his wife and two little children, arriving in the winter at New York City, where he bought a one-horse wagon, and started up the North River on his overland journey to his new home, which he reached abut the middle of January, after twenty four days of almost insufferable hardship, arrived at his destination, and purchasing an improvement, made that summer the first three firkins of butter for market which were shipped from the town. He soon increased his dairy to 30 cows, and built him a house, three stories in height, on the point of a high hill overlooking the village, from which he took the name of "High Jimmy" McCormick, as he is popularly known throughtout the surrounding country.

Among the earlier settlers are also Henry Young, who came from Tompkins County in 1826, and settled where his son William now lives. George Updike came from Seneca County in 1828; Benjamin Edwards from Newfield, Tompkins County in 1830; Wm. Atkins from Enfield in 1832; Abram Williamson and daniel Richey from Ulysses in 1827, settling in the west parat of the town. John J. Dutcher settled near Krusen’s in 1826. John Rogers from Lansing, Cayuga Co., settled in the south part of the town, near the old Catholic church, in 1832. Hiram Burger, who lives near Greenwood village, came with his father Ezekiel Burger, from Troupsburgh, where he was born in 1815. Enos Smith came from Seneca Country in 1828, and settled on the hill west of the village. Homer Mallory, supervisor of Greenwood for the past six years is a son of Samuel Mallory, who came from Connecticut and settled near Krusen’s Corners in 1838. John Balsby settled in the northwest corner of the town in 1828.

Charles C., son of Ezra Stephens, was the first white child born in the town, his birth occurring in 1824. The first marriages were, on Christmas 1828, Hiram Putnam, to Lucinda, daughter of Ezra Stephens; and June 14, 1829, Redmond Davis, son of Levi Davis to Jane, daughter of Nathaniel Porter. The first school was taught by Sarah Carr. 

When the first settlements were made, the valley was filled with a heavy growth of nutritious herbage, upon which the cattle were driven up from the river to fatten. The first settlement south was Mr. Olmstead’s, now Rexville.

Richard Krusen came from Dryden in 1825, and opened the cross-roads, four miles west of Davis’ Store, towards Andover, where he kept a tavern until the country had become well settled, and railroads changed the routes of travel. Acting as a sub agent for the land-office at Bath, he did much towards attracting a good class of settlers from his native country.

In 1828, the first clearing west of Greenwood was that of Joseph Crossing, and just beyond on the Ridge road, lived Randall Pease and Daniel Richey, who came in 1827. The next place west, on the hill, was Aden Lewis, William Brown, and Timothy Terpeting. Then, nearly opposite each other, were James and William Bess; and back some distance from the road was John Potter. Timothy Holloway from Dutchess County, on the right was the next settler, and half a mile through the dark woods was the little clearing of Elisha Sanford. Joining the Sanford place was Anson Cook, Esq. Robert Richards lived where Alva Richards, who came in 1834, now lives. Nathaniel Richards, their father, came in 1828.

Enos Mead, from Newfield, Tompkins Co., made the first clearing west of Krusen’s Corners in 1827. His son, Alvin Mead, who came a few months later, brought the first wagon into that part of town, his brothers chopping the road ahead for him to drive through. Mr. Mead contracted for 1050 acres of land, and brought several families of his relatives. The Mead settlement became a centre of improvement, and a post-office was established there in 1842, with Alvin Mead postmaster. The post-office was discontinued on the opening of another at Rexville, in the north part of West Union.

William Burrows was an early settler still west, near the county line, and built a saw mill in 1830. Joshua Goldsmith, a son-in-law of Derrick Krusen, the school-teacher, lived near him. Half a mile north of Krusen’s Corners was the log school-house where Sophie Phelps taught school. There were many small clearings in that part of the town as early as 1830.

A spring of salt water was discovered by Ezekiel Burger, a native of Delaware County, while hunting, before the settlement of the town. This spring was a resort for deer and elk, and was well known by the Indians, who watched for them as they came to drink its waters. Mr. Burger and a Mr. Mathews had built a couple of cabins at the spring, one roofed with elm-bark, and the other with what was called a "stake and ridered roof;" that is, built in at the top, and the rough-split shingles laid in courses and held in place by logs laid over each course and held in place by stakes or wooden pins. The spring was closed to the creek, but a drill had been erected and a well sunk sixty-four feet by hand, when the drill was broken off in the well. Boiling was carried on in kettles until Mr. Davis bought the land, and Mr. Mathews died, when the enterprise was abandoned.

After the well had been abandoned for a few days the settlers would come and pump out the water and boil down a sack of salt in Burger’s kettles until they were taken away. Salt was hard to get in those days, and the well was much frequented. Afterwards, when the roads were opened salt was important so cheaply that the well was abandoned. In 1870, a well was drilled at this place for oil to a depth of 600 feet, resulting in gas, which would burn freely for several minutes, and salt water in small quantities with some indications of oil. The well was abandoned when the contract under which it was drilled had expired. The north part of the town, west of Bennett’s Creek, is quite broken, and its settlement is comparatively recent. The western and central part, which has the appearance of high rolling prairie, is well cultivated, and the view from almost any point is magnificent. Descending into the deep, narrow valley of Bennett’s Creek, in the north part of the town, the change is very abrupt. The hills on either side of the deep, narrow valley are cleared and cultivated, and a continuous row of farm-houses extends along the left bank of the stream to the village, some three miles south. Following the hill on the right bank of the stream is the partially completed grade of the Rochester, Hornellsville and Pine Creek Railroad, which was abandoned in 1875, and which has made the town of Greenwood famous for its refusal to pay its assessment of tax upon bonds issued for its construction.

One of the principal citizens of the town, Alexander H. Stephens, the first settler, is a son of Col. John Stephens, one of the earliest settlers of the county, and Olive Franklin, daughter of Capt. John Franklin, the hero of the Wyoming massacre. Uriah F., Phineas, Elias, John H., Alexander H., and Franklin Stephens are the members of the family. Alexander H. Stephens, who was born in 1801, has been a leading spirit in the affairs of this town, from its erection to the present time. Mr. Stephens is a man of high literacy attainments, and one of the most influential citizens of the town. He was a member of the State Legislature I 1848, and ably represented its interests while there. His wife, Mary M. Davis, was a daughter of Levi Davis, the firs merchant, and for years the leading business man of the town. James H. Stephens, son of Phineas Stephens, and Redmond Davis, and John Davis, both sons of Levi Davis, have also been sent to the State Legislature from Greenwood.

The village of Greenwood contains nine stores; harness, cabinet, wagon, shoe and blacksmith shops; a large steam saw-mill, and flouring-mill; the "Stage House" and Greenwood Hotel, a large three-story building; two churches, a fine two story school-house, and an unusual number of fine residences. Elias V. Davis has conducted a jewelry establishment here since 1841, at which date there was but one store in the place. The village extends along both sides of a single street filling the space between the hills and the creek, and a street starting from the central part of the village and continuing west, and contains about 200 inhabitants. There is a flouring-mill at Rough and Ready, a mill settlement in the south part of the town, where was once a post-office, named from the Rough and Ready Presidential candidate; and north of the village are two flouring-mills and a saw-mill.

The first town election of the town of Greenwood was held at the house of Levi Davis, March 6, 1827, when the following officers were elected: Levi Davis, Supervisor; Anson Cook, Town Clerk; David Murray, Randall Pease, Uriah Ingley, Aden Lewis, Commissioners of Highwas; Jacob Manning, James Bess, Overseers of the Poor; Abram V. Olmstead, Joseph Batchelor, Thomas Johnson, Commissioners of Common Schools; John H. Stephens, Collector; John H. S. Stephens, Ira S. Mills, Constables. John J. Holt, John Stephens, Amos Lewis Jr., Linden Lewis, Francis Pilgrim, Amos Labar, Enos Mead, John Krusen, Wm. Brown, Wm. M. Blair, Sylvanus Strang, wm. Crampton, Joseph Davenport, Seba Norton, John Matteson, and A. V. Olmstead were made pathmasters.

The name of Greenwood was given it by Hon. Alexander H. Stephens, through whose exertions a half mile was added to the east end of the town from Jasper.