The toll houses were small frame structures and the gates simply heavy poles to raise and let down after the manner of the beam that lowered and lifted up “the old oaken bucket that hung in the well.”

Going westwardly from the Ohio State line, in Indiana, the first tavern was that of James Neal, at Sycamore Valley. Of Neal but little can be gleaned beyond the fact that he kept tavern at this point for several years.

The next tavern was Clawson’s, a brick building, erected about the year 1818 by Robert Hill. It stood a little distance north of the road, and near the western end of the line before mentioned, as having been located but not used, and was subsequently torn down and rebuilt on the traveled line. It is said that Robert Hill’s daughters hauled the brick for their father’s house in an ox cart. Clawson was a tall, muscular man, and beyond these facts concerning him, he is lost to the memory of the oldest inhabitant of Indiana. West of Clawson’s the first toll gate in Indiana was encountered. It stood near Glen Miller Park and almost within the suburbs of Richmond. This gate was moved several times, but never over a mile from Richmond.

The city of Richmond is the first large town on the line of the road within the borders of the State of Indiana, and the road forms its Main street. It is four miles from the Ohio line, and the county seat of Wayne county. Its present population is 25,000.

The first tavern of the road in Richmond was kept by Charles W. Starr. It was a regular old pike tavern, with extensive stabling and drove yards attached, occupying one-fourth of a square on the northeast corner of Eighth, formerly Fifth street. The building was of brick, known in later years as the Tremont Hotel. It is still standing, but not used as a hotel or tavern. Charles W. Starr was a man of medium size and of Quaker faith. He wore the Quaker garb, had Quaker habits, and was esteemed a good citizen. Some of his descendants are still living at Richmond, and three of his sons are prominent and active business men of that place.

A short distance below Starr’s, and between Sixth and Seventh streets, stood Sloan’s brick stage house, and its proprietor, Daniel D. Sloan, was at one time postmaster of Richmond. This tavern was headquarters for two stage lines, one running to Indianapolis and the other to Cincinnati. The Cincinnati line had opposition, and by cutting rates the fare was reduced by the competition and during its continuance, from five dollars to fifty cents for the round trip, distance seventy miles direct. A portion of Sloan’s old tavern still remains, and adjoins Roling’s hardware store. Sloan was heavy set, fleshy, and well poised for a tavern keeper.

On the south side of the road, between Seventh and Eighth streets, William Nixon kept a tavern on the site of the present Huntington House. He was a spare, sinewy man, of the Quaker faith. He kept the tavern at the point named from 1840 to about 1843.

A noted tavern was Gilbert’s, on the northeast corner of Sixth and Main streets. Joseph W. Gilbert kept this house for many years. It was a two-story frame building, pebble coated. Gilbert was tall and slim, polite and affable, and had many friends. He suffered the misfortune of going blind, and died at Richmond in 1890, in the ninety-second year of his age. When barely able to distinguish large objects he walked much up and down the streets, asking persons he met to tell him the time of day, always pulling out his watch and holding it up for inspection. At one time when Gilbert was moving a part of his tavern building, Charles Newman, on passing along, inquired of the old landlord, whose house was noted for its cleanliness, how many bed bugs he found. Gilbert replied with indignation, “Not a single one.” “I believe you, Joseph,” said Newman, “for they are married and have large families.” Most of the early taverns of Richmond were in the western part of the town.

It is related in the latest history of Indiana, that Jeremiah Cox, one of the earliest settlers in Richmond, regarded with disfavor the scheme of building up the town; and is said to have remarked, that he would rather see a buck’s tail than a tavern sign, and his sincerity was made evident by the fact, that he did not make his addition to the town plat until two years after the date of Smith’s survey, or two years after Philip Harter had a tavern sign swinging near a log building on lot 6, South Fifth (Pearl) street.

Another early tavern of Richmond was kept at the northwest corner of Main and Fifth (Pearl), sign of the green tree, by Jonathan Bayles, and another, of later date, on Fourth (Front) street, near the southwest corner of Main, by Ephraim Lacey. Harter soon afterward kept a tavern at the corner of North Fifth (Pearl) and Main, where the Citizen’s bank afterward stood, then called Harter’s corner.