The pioneer cotton spinner of Willimantic was Perez O. Richmond, who came here from Rhode Island some time in the year 1822, and purchased the privilege at the lower end of the borough now known as Willimantic Linen Company’s Mill No. 2. On this site he built a mill of wood, about forty by sixty feet, one and a half stories high, put in machinery and commenced making cotton yarn. He also built a cheap row of tenements, six in number, just north of the mill, for his operatives. Mr. Richmond continued to run this mill until 1827, when it passed into the possession of Messrs. Hawes, father and son, of Providence, R. I., who made extensive repairs to the mill and tenements, and also erected a large boarding house and the best store in the place.
In 1823 Major Matthew Watson, Hartford Tingley, Rathbone Tingley and Arnnah C. Tingley. all of Providence, R. I., purchased the privilege and land adjoining, at the upper end of the village, and formed a corporation by the name of the Windham Cotton Manufacturing Company. They built a dam across the river and put up a mill, which is now the south half of the west mill belonging to the Windham Company. Here they put in machinery and commenced making cotton sheetings and shirtings. They also erected some six dwelling houses for two families each, which were known then,. as now, as the “Yellow Row.” A store on Main street at the head of the row of houses was built and filled with goods for the operatives. Arnnah C. Tingley, one of the owners, removed here from Providence and became the local agent of the corporation. He built and occupied the dwelling house west of the store on Main street. The erection of a dam for this corporation caused a set back of the water for two miles or more, overflowing large tracts of meadow on this river and on Hop river and Ten Mile river as well. This caused much damage to lands overflowed, and quite a large amount was paid by the company in settlement of such claims.
About the time the Windham company commenced operations Deacon Charles Lee, of Windham, purchased the site of what is now the Smithville Company’s property, and erected a mill for the manufacture of cotton goods, four dwellings and a barn and store house. In the spring of 1827 a store was erected by him on the corner of Main and what is now Bridge street, in which were kept a general assortment of dry goods and groceries. Associated with him in the store was Royal Jennings, who came from Windham and remained here until 1840, when he removed to Milwaukee, Wis. Deacon Lee removed to Norwich and was for many years the head of the firm of Lee & Osgood. They were active business men and took a deep interest in the moral and religious welfare of this young and growing community.
In 1824 Messrs. William, Asa and Seth Jillson, three brothers from Dorchester, Mass., purchased land on the south side of Main street, with the water privilege attached thereto, built the dam and laid the foundation of a cotton mill on the site of what is now the Linen Company’s spool shop. At that time this was the largest cotton mill in Willimantic. In connection with the manufacture of cotton goods. quite an extensive business was done by this firm in the manufacture of machinery for cotton mills. The stone building opposite the mill, and five dwellings for four families each, were erected by this corporation. An additional mill was erected a few rods below for the same purpose, greatly enlarging what for that time was an extensive business in cotton manufacture. The senior brother built the stone house between Main and Union streets for his residence. Asa built the fine house on the south side of the river, and Seth built another on South Main street, the three being at that time the finest residences in the village.
Thus, in 1826, Willimantic had four cotton mills in successful operation, and began to assume considerable importance: Peter Simpson built a one-story dwelling on the site of the present Brainerd. House. The old State powder works had passed into the hands of Samuel Byrne and David Smith, who were operating under the firm name of Byrne & Smith. Guy Hebard had erected a brick house on the south side of the river and opened it for the entertainment of the public. Of this we have already spoken. Here all public gatherings, Fourth of July celebrations, trainings, dancing schools, balls and other carousels of festivity were held. The old Hebard tavern was known far and wide. The first grog-shop in the village was opened by Thomas W. Cunningham, and was located on what is now the west corner of Walnut. and Main streets.
Philip Hopkins, one of the first to build on private account, built a house on what is now the site of Levi A. Frink’s block on Main street. He also had a general blacksmith shop on Main street, near his residence. Alfred Howes had a similar shop at the lower end of the village at the same time., He soon gave up the business, purchased land between Main, Union, Jackson, Maple and Church streets, and engaged in the first drug business in the village, in association with Newton Fitch and Doctor John A. Perkins of Windham.
Jairus Littlefield, one of the earliest settlers in the village, built and occupied a house on Main street where C. E. Carpenter & Co.’s store now stands. He spent the remainder of his life here, representing the town in the legislature, and was a trial justice for many years. Stephen Hosmer built the second house on Pleasant street, west of Young’s residence. He moved here from Columbia in the fall of 1827. He was a lively business man, owned a good deal of land and was an extensive farmer. He also owned the turnpike road from Hebron to Hebard’s tavern. At that time there were no streets south side of the river except Columbia Turnpike (now Pleasant street), Card road and South street. Main street was the only one on the north side of the river. Through the efforts of Mr. Hosmer the courts ordered Bridge street to be opened.
About the year 1825, under the administration of John Quincy Adams, a post office was established here by the name of Willimantic Falls, which form the name retained until about 1833, when the `1 Falls ” was dropped from it. Henry Hall, at that time a bookkeeper and clerk for the Windham Cotton Manufacturing Company, was appointed postmaster. The most convenient location seemed to be at the Hebard -tavern and there the office was established and kept, Mr. Hebard having charge of the office as Mr. Hall’s deputy. All the mails in those days were carried by stages or other vehicles, and the tavern was a handy place for mail carriers to stop at. After Mr. Hail resigned the position George W. Hebard was appointed postmaster, and he removed the office to the stone store opposite the present Linen Company’s spool shop. Here it remained for some time. Thence it was moved to a building near the Iron Works bridge, about opposite the south end of the Linen Company’s Mill No. 1. Mr. Hebard kept also a grocery store. The next postmaster was Colonel Roswell Moulton, who after keeping the office for a while at the old location, removed it to his new store nearly opposite the building now occupied by Edward F. Casey. There it remained until July 1st, 1843, when Lloyd E. Baldwin was appointed postmaster and removed the office to the store nearly opposite the Revere House. The pay of the office at that time amounted to about $300 a year, being based on commissions. The next postmaster was Joshua B. Lord, who removed the office to his store in what is now Hanover’s Block. He was succeeded by William L. Weaver, who removed the office to his store, but retained it only a few months. James H. Work was the next occupant of the office, which was now kept in the twin buildings west of the Franklin Building. Then followed Thomas Campbell, whose office was where the Adams Express Company is now located. He was succeeded by William H. Hosmer, whose term closed in July, 1861, he being succeeded by James Walden, who held the office eight years. His successor was John Brown, who held the office twelve years, and filled the post of assistant for as long a term on the end of that. He was succeeded by his predecessor Mr. Walden, who held it for an equal term of years, and gave place to Henry N. Wales, the present incumbent.
No private individual contributed more in his time to the growth and prosperity of the village than Daniel Sessions. He was a farmer, living some two miles west of. the village on the turnpike road to Coventry. Almost all the brick used here in early days were made and furnished by him. He also furnished timber, erected the frames and finished the buildings ready for occupancy in many instances. Apollos Perkins, William W. Avery and John Brown, living in the near vicinity, did more or less in this line of business, contributing essentially to the growth and prosperity of the village.
Source: History of Windham County, Connecticut, Bayles, Richard M.; New York: W.W. Preston, 1889