John Nussman was the first white settler, wagon maker by trade, and operated a whiskey still in the woods behind his cabin.
John Tillson operated a store in one room of his log cabin home, and became Hillsboro's first merchant. He opened a general store where he also conducted the duties of county postmaster, treasurer and his land agency.
John Prentice opened the second store in 1825 after moving here from St. Clair County.
Benjamin and Joseph Miller were given lots for establishing a tanyard at the foot of Seward Street in what is now Central Park.
John Hawkins Rountree [brother of Hiram] received a lot to open a blacksmith shop and he became sheriff in 1826.
Early tavern keepers were licensed and were required to furnish people with food and lodging, provide stables and feed for horses. The maximum prices in effect in 1823 were: whiskey, wine or brandy- 37 ½ cents per pint; cider-12 ½ cents per quart; lodging-12 ½ cents per night per person; stable fee-12 ½ cents per horse; feed for horses-12 ½ cents per head; breakfast- 12 ½ cents; dinner and supper 18 ¾ cents each.
James Rutledge opened the first tavern-hotel in 1825 on the site of the present Red Rooster Inn. He had a sign embodying a large tiger on a white background surrounded by the owner's name and occupation.
David B. Jackson operated an Inn which was a 2 story frame hotel and tavern known as the American House on the southeast corner of Main and Wood streets in 1829.
C.B. Blockburger a tinner and brickmaker who made bricks used in building a 2 story brick stagecoach inn on the northwest corner of Main and Tilson streets in 1830.
Wesley Seymour and John Nussman were wagon makers.
John Meisenheimer and William Loomis were carpenters.
Jacob Wilson, John Slater and Deacon Alexander Scott were shoemakers.
Dr. Levi Boone – physician. Was elected coroner in 1830.
Charles Holmes, Thomas Sturtevant and John S. Hayward were also early merchants.
James Blackman, Alfred Durant and E.B. Hubbell were furniture makers.
Pioneer blacksmiths included Nathan and Burton Harmon, W.A. Morrison, Kimball Prince, Fred Hillsabeck and Ned Gorsage.
Early brick masons and makers were: John Dickerson, David Eddy, Ira Boone, Isaac Horner and Hudson Berry.
Solomon Harkey opened a tanyard about 1830 and built a 2 story frame house on Broad Street in 1832.
Others were D.B. Starr, James Card, Peter Hill, Lloyd Marten, “Granny” Wright and son James and Stephen Fullingsworth, “keeper of the stray pen”.
The five Clotfelter brothers – Amos, Lee, William, D. Stokes and James, and their sister, Zikpha, arrived in 1833 from North Carolina.
John Tillson built the first brick house in the county. It was started in 1825, it was a massive 2 story structure located on the northwest corner of Main and Tremont streets, and was completed in 1827. It was built by John Dickerson and David Eddy from bricks made by Isaac Horner, a talented black man who was raised a slave in Maryland and was freed there by his master. Clay for the bricks was dug from Tillson land.
Also built during that period was a 2 story brick and stone residence erected in 1831 by Hiram Rountree on the southwest corner of Rountree and Wood streets. Four generations occupied the property until it was torn down in 1962.
The Gazeteer of Illinois reported in 1834, Hillsboro, the seat of Justice of Montgomery County, has 6 stores, 4 taverns, 3 blacksmiths, 2 tanneries, 1 shoemaker, 2 tailors, 1 tinner, a post office, land agency, 50 families, 250 inhabitants. Principal roads pass through Hillsboro.
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