Winona, the county seat of Montgomery County, is situated on the Illinois Central rail-road, at its intersection with the Richmond & Danville road, two hundred and seventy-one miles from New Orleans and two hundred and seventy-nine from Cairo. It has a population of twenty-one hundred people, contains between twenty and thirty substantial stores, and does a trade of over half a million dollars a year. Winona has a good bank with ample cap-ital, which moves the extensive cotton business of the town, which amounts to over two thou-sand bales yearly, the bulk of which goes East.
Winona is said to be the name given by an Indian chief to his first-born female child. The building of what is now the Illinois Central railroad caused a small town to spring into existence within two miles of Middleton, then the educational center of Mississippi. The new town was christened Winona, and it soon distanced its older neighbor. Middleton is now a place of the past; its famous schools have been scattered over the state, but Winona lives and grows. Winona has two banks. Its railroad facilities make it a very desirable location for mills and factories of any kind, and such enterprises would receive great encouragement and support in the town. At present there are here two carriage and wagon factories and a gristmill. A compress has been talked of, and will soon be built if it has not been already. Among the other institutions of Winona is the rifle corps, of which it is justly proud, an exceedingly well-drilled body. The town also has a brass band and a capacious public hall.
Winona is in no respect lacking in educational facilities. There are three very well organized public schools, largely attended. Two private academies of a high order are also located here. Winona is in the mineral district in which Duck Hill is the most conspicuous point, and must profit by the general development of the district, some of its capitalists being interested in Duck Hill’s mineral land company.
Winona has the following named churches: Methodist Episcopal, Presbyterian, Baptist and Christian, all strong of membership and having good houses of worship; and Methodist, Baptist and Presbyterian colored congregations all have adequate buildings. Here are two Masonic lodges, one of white men, the other of blacks. The business buildings in Winona are mostly of brick, and with few exceptions they are large and in every way creditable to their owners and to the town. The Winona Times is published by Walter N. Hurl. It is in its ninth volume, in size a five column quarto. The Winona Democrat was published for a time under that name and was afterward known as the Advocate.
Duck Hill is the name given to a pleasant little town in Montgomery County, and situated on the Illinois Central railroad between Winona and Grenada, at a distance of two hundred and eighty-two miles from New Orleans, ninety-nine miles from Jackson, and two hundred and sixty-eight miles from Cairo, Illinois. Duck Hill lies in one of the most beautiful valleys in the state, which extends for miles up to the road. Near the town towers the real hill called after the Indian chieftain Duck, while on either side, for miles up the valley, and running back for miles on ridges on either side lie the hills lately discovered to be rich in ores. Almost within a stone’s throw of the town in its rear there appears to be a solid mountain of iron. Professor Johnson, the well-known United States geologist, has distinctly located these ores. A strong company of local and outside capitalists has been formed under a state charter to purchase and to operate these mineral lands.
Other towns in Montgomery County are Lodi, Mayfield, Sawyers and Kilmichael.
Source: Biographical and Historical Memories of Mississippi, Goodspeed Publishing Company, 1891