Greensboro, which lies at the southern tip of Orleans County, is bounded on the northwest by Craftsbury, on the northeast by Glover, on the southeast and southwest by the Caledonia County towns of Wheelock, Stannard and Hardwick.

The construction of the Bayley-Hazen military road ordered by George Washington in 1776 led to the settlement of Greensboro. The road was built for an anticipated invasion of Canada that never happened. The road reached Greensboro by 1779 and continued northwest before the project was abandoned. Wooden blockhouses, including one at Greensboro, were erected at intervals for protection. Responding to Indian raids on Peacham in 1781, four scouts, all young boys, were stationed at the Greensboro blockhouse near the southwest corner of Caspian Lake. The four were surprised by Indians who killed two of the scouts and took the other two to Quebec. They were later traded for Indian prisoners in Vermont.

The township was granted to Harris Colt and 66 associates in 1781. The town’s original name of Coltkiln was later changed to Greensboro in honor of Timothy Green, another proprietor. There is no record that either man ever lived in Greensboro, according to the town’s website.

Greensboro’s first sawmill and blacksmith shop were built in 1790, and a second major road was built by Timothy Hinman between 1791 and 1793. That road, known as the Hinman Settler Road, branched off from the Bayley-Hazen Road and ran northeast to Derby. Those two roads were of major importance to the settlement of northern Vermont.

By 1795, there were 23 families and a total of 108 residents in Greensboro. The railroad reached the town in 1872, spurring a period of prosperity with a large sawmill, a box factory and numerous stores.  In the 1870s, the Vermont Historical Gazetteer said the village of Greensboro at the eastern extremity of beautiful Caspian Lake had “some 25 neat dwellings, a hotel, three or four stores, excellent mills for sawing and grinding,” and several shops.

In the early 1900s, the character of the town began to change, evolving into more of a summer community. The number of dairy farms declined, as did the year-round population. Greensboro, according to the town’s website, now reflects a mix of groups who historically arrived at different times: the English of the 1790s; the Scots of the 1830s; the Irish of the 1870s; the Portuguese and French Canadians of the early 1900s. The summer community includes authors, academics and professionals, many of them drawn to Greensboro by beautiful Caspian Lake. One of the most notable summer residents was former Supreme Court Chief Justice William H. Rehnquist, who died in 2005.

In the last few years, many Greensboro visitors have been drawn by the Hill Farmstead Brewery, which was ranked number one in the world by Ratebeer.com in 2013. Its fame led to long waiting lines, but relief is expected this year due to an expansion that is projected to double the brewing capacity. Owner and brewmaster Shaun Hill’s family has been in Greensboro more than 200 years, and his brewery’s logo is adapted from a sign that once hung in his great great great grandfather Aaron Hill's tavern in the early 1800s.