By 1750, the upper Cashie River basin had become a center of commerce, population, politics and court activities. Every landing from the courthouse for two miles down river was the scene of busy shipping and trade - especially those landings with access to the main county roads. With the influx of people and trade, a pressing need for a town arose. It is not recorded who the leaders were of this movement, but in 1752, enough interest had been generated to have an act passed in the Colonial Assembly at Edenton creating the town of ''Winberly'' at Blackman's Landing on the West side of the Cashie River below Gray's Landing. It is not known what stopped formation of this town, but it was undoubtedly due to influence from the courthouse area of Cashy.
In 1756, in spite of the lack of encouragement from the government, cultivation of tobacco had increased so much that warehouses were established for its inspection before being exported from the Province. Thomas Whitmel's warehouse on Cashie above Gray's was one such government station. As such, his landing became a center of trade.
By the 1760s, the landing at Gray's was the site of much shipping and water commerce. William Gray extended a formal offer of one hundred acres for a town, and on February 14, 1766, the Speaker of the Assembly presented a petition from sundry inhabitants of Bertie County asking for the creation of a town at Gray's landing. Since the courthouse, prison, and a small village were located farther up the Cashie River at what is now Hoggard's Mill, opposition arose to this plan for a new town. A counter petition was presented to the Assembly by other inhabitants that a town be built at the courthouse. The Assembly resolved that the petitions by shelved and that Cullon Pollock, Edward Vail, James Blount, Benjamin Wynns, and Jasper Charlton be appointed to view both sites and present at the following session of the Assembly which of the two was the most convenient and best site at which to erect a town.
The main factors affecting this committee's decision was the crooked, narrow condition of the river past Gray's to the courthouse and the fact that all exisiting buildings at the courthouse were in a poor state of condition while Ballard, Gray, and others had a thriving business at the lower landings.
When the Colonial Assembly met in December, 1767, the Committee returned in favor of Gray's landing, and thus, on January 8, 1768, the Assembly passed an act to ''create New Windsor '' on the Cashie River. Cullon Pollock, David Standley, and Thomas Ballard were appointed commissioners to sell lots on which each purchaser had two years to build a suitable edifice at least sixteen feet square with a brick chimney.
Immediately upon the establishment of this new town, a bill was introduced in 1768 to move the courthouse and prison to Windsor. However, this met with stiff opposition from the group at 'Cashy,' and for several years nothing was done about it. In 1773, a petition was reintroduced by 94 citizens to the town of Windsor which was ratified by the Assembly and the courthouse was moved to Windsor. In 1774, the Assembly appointed William Gray, Thomas Ballard, Thomas Clark, Zedekiah Stone, and David Standley to build a courthouse, prison, pillory and stocks in the town of Windsor, and Windsor has been the county seat for Bertie County ever since.
In 1775, Samuel Clay Milbourn, tavern owner, sold these commissioners a half-acre lot in town for ten pounds for the purposes of erecting a courthouse. This is the same site that the present courthouse buildings are on today.
The first businesses to appear in the newly-formed town were necessarily shipping merchants, since it was a river landing site. Chief products for export were tar, pitch, staves, turpentine, and foodstuffs.
Religion and education were also a part of the growth of early Windsor. Services were held in various homes by visiting ministers, and services were attended at the Parish Church in Merry Hill. Early education took place at home with tutors. Boarding students were taken in and taught with the children of the home. Sometime around 1800, Oak Grove Academy for young men was formed near Windsor.
A Masonic Lodge was formed in Windsor in 1772, chartered as Royal Edwin Lodge #4, later renamed in 1822 to Charity Lodge. An attempt was made to erect a lodge building in 1883, but insufficient funds ended the endeavor. In 1843, the Lodge was meeting over the W.S. Pruden store. Finally, the Old Brick House, said to be the oldest brick building in Windsor, was purchased in 1848 and after several remodelings has been used continuously by the town's oldest organization.
By 1800, Windsor was quite an inland shipping center and is referred to in some documents as the Port of Windsor. Ten ships listed Windsor as their home port in Registry Books. The largest of these was the schooner Susanna, owned by Jonathan Jacocks, Benjamin Cook, Robert West, and John H. Pugh, with tonnage of 158 tons. She was equipped for West Indies trade. The rest were primarily coastal traders. The ten registered vessels had a combined tonnage of one million pounds of cargo.
The two main avenues of land traveled into Windsor were the Halifax Road and the Cashy Road. A portion of the Cashy Road was laid out in 1717 and travelled through the northeastern section of the county. The Halifax Road existed in 1770 and entered Windsor from the west. This became the main thoroughfare due to the early seat of governmental affairs at Halifax, and later as the Post Road from Bertie.
By 1832, Windsor had grown until it had its own newspaper, the Windsor Herald. There were, according to Volume I, Number 22 of the paper eight businesses located and prospering in town. The population court revealed 128 white and 160 colored inhabitants, including three doctors, two lawyers, three shoe makers, a carpenter, and a tailor. Other businesses included a blacksmith, ice houses and warehouses along the river. There were two taverns or inns, four cotton gins, a turpentine still, a printing office, a post office, and twenty dwellings. The courthouse had been built a few years before, but a new jail was being constructed.
In 1847, an act was passed in the General Assembly which incorporated the town. The newly-incorporated town had now become a farm-oriented community. Plantation life prevailed, and the town became the church, social, and trade center for the many famers in the surrounding area. It also became a center for banking under the state chartered N.C. State Bank. The Windsor Branch of this bank was founded sometime in the 1830s and, by 1860, could boast of a million dollar capital and of being one of only two in the northeastern region.
By 1850, as the first hints of the upcoming Civil War began to rage, the white population of Windsor was 113, with lawyers, doctors, a shoemaker, confectioner, mechanic, tailor and painter. By 1860, the overall population had increased to 384, which included 170 whites, 28 free blacks, and 186 slaves. Professions in 1860 included coachmakers, merchants, doctors, seamstresses, lawyers, and cabinetmakers. At this time the Bertie County area's largest crop was cotton which supported large plantations. Only four other counties in the state produced more cotton than Bertie at this time. There were 25 plantations with at least 1000 acres and there were 35 slaveholders who owned 50 or more slaves apiece. These two figures made Bertie County and Windsor one of the wealthiest areas in the state prior to the Civil War.
Windsor was spared most of the ravages the came to the South with the Civil War. After the fall of Roanoke Island, the Federal forces occupied the entire sound region and held much of it throughout the war. Episcopal Bishop Atkinson was only able to visit Windsor once between 1860 and 1865, as it was held by northern troops. His journal shows a report from Reverand Cyrus Waters in 1863 stating that he had not been disturbed in the dishcarge of his duty by the enemy and that the church had given freely of its belongings for the war effort.
There was sympathy to be found for both sides during the occupation, and a certain amount of trade was conducted with the northern forces. The many excursions of the northern gunboats from Plymouth up the river to Windsor brought fire from partisans in the area. Two such encounters took place at the County Farm Landing and at the Hoggard Mill Bridge. Windsor served up her sons to fight on the battlefields across the South and suffered at home as did many other rural area. High prices, scarce commodities and lack of some necessities were prevalent. The end of the war left the area land poor and depressed.
Community life in the early 1870s centered around surviving the aftermath of the Civil War. Politics was the issue, with the Windsor township being highly disturbed over President Grant's management of the South. In 1874, the people of the state were still reeling from the shock of the war and the humiliation of reconstruction. They were ready to resume the reins of self-government which federal troops had denied thus far. Patrick Winston, Jr. of Windsor was a man who stood up for his ideals and played a major role in the call for a Constitutional Convention to rewrite the state constitution. As a result of Winston's work, the North Carolina state constitution was rewritten and North Carolina began to move ahead for the first time since the end of the Civil War.
The town's physical growth in the twentieth century has been gradual. The city limits established in 1768 were not expanded until 1883, and have since been changed several times to incorporate small subdivisions and other growth, mainly on the north and west sides of town. In 1959, the small town of Bertie on the south side of the Cashie River merged with Windsor. Since the 1890s, nearly eighty buildings, mainly residences, have been constructed in the area of the historic district, filling in the blocks of King, Queen, and York streets. The business distrcit remains concentrated on King Street above the courthouse and west along both sides of Granville Street. The 1970 population of the town was 2,199, only slightly larger than the 1924 population of 1,800.
Perhaps because of slow development, Windsor has retained intact enough of its physical fabric from the turn of the nineteenth century through the early twentieth century to form an historic district representing the evolution of a small eastern North Carolina town. The town's main thoroughfare, King Street, remains tree-lined and residential, with houses exhibiting the Georgian, Greek Revival, Victorian, and Colonial Revival styles of architecture. The business district possesses a number of two-story commercial structures dating from the turn of the century which feature handsome brickwork.
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Windsor was granted a US Post Office on January 1, 1795, and its first Postmaster was Mr. William Benson. It has been in continuous operation ever since.