Three fourths of a mile from his master's mansion in Madison on Hunter Street, with his large plug tobacco factory across the street on the corner (where [HW: in] 1937 stands the residence of Dr. Wesley McAnally,) in some "quarters" which Nat Pitcher Scales had near Beaver Island Creek, Anderson was born to slave mother, Martha Scales of a father, "man name uh Edwards." Baby Anderson was the slave of William Scales, at one time the world's largest manufacturer of plug or chewing tobacco and he was named for Henry Anderson, the husband of Mrs. William Scales' sister. Cabins here "quarters" consisting of three or four log ones. Cabins were near the old "free white schoolhouse" or rather the "schoolhouse" for whites.
Rolling around the yards with the other pickaninnies, Anderson passed his babyhood, and when he was a boy he went to be house boy at Marse Jim Dick Cardwell's on Academy Street facing Nat Pitcher Scales' home, later that of Col. John Marion Gallaway. Here he learned good manners and to be of good service. Later he was houseboy in the big house just beyond the Methodist church at James Cardwell's who had a mill five miles west of Madison and whose wife was Sallie Martin; granddaughter of Governor Alexander Martin. Here Anderson learned more good manners and rendered more good house boy service such as sweeping floors, bringing in "turns" (armfuls) of fireplace wood, drawing water from the yard well and toting it into the house, keeping flies off the dining table, carrying out slops and garbage, for every town house had its back lot pigs.
Larger [HW correction: Later] Anderson was hired to Nat Wall, (colored) farmer and blacksmith, then to Joshua Wall, white planter of Dan Valley northeast of town a few miles.
White men would get contracts to have the mail carried to various towns and Anderson Scales was hired by one of these contractors to carry the mail from Madison to Mt. Airy, fifty miles distant in northwest Surry County. He would go by horse and sulky (sulky) on Monday, return on Wednesday; go on Thursday, return on Saturday. This was in the late 1870's and 1880's.
During the tobacco season, he worked in factories in Winston (no Salem then) and Greensboro. Then he worked in Nat Scales' factory in Madison and in that of his former Marster, William Scales. He married Cora Dalton and started his home a mile up the Ayresville road from town.
The railroads having come with the consequent transporting of freight to and fro, Anderson started a public draying business of one horse and a wagon, which lasted thirty eight years and was given up by him to his son-in-law, Arthur Cable who now, in 1937, has an auto-truck and hauls large paper boxes from the Gem Dandy Suspender and Garter Company located across Franklin Street from Anderson's house boy home, that of James Cardwell, to the post office. From the freight train depot, Arthur hauls merchandise also in paper cartons to the feed stores which do not own an auto truck of their own, and he hauls to the garter factory a few two by three foot wooden boxes loaded with metal fillings for the suspenders. This is a complete contrast to the loads "drayed" by Anderson through the 1880's, 1890's and the 1900's to about 1915 when the automobile began to change the world of transportation, and Anderson's one horse wagon dray business along with it.
For thirty-eight years Anderson met every train to capture the trunks of visitors or "drummers" in town. Two immense hogheads packed with leaf tobacco was sold on the floors of Webster's ware house and Planters' warehouse. Two stacks of tobacco baskets loaded with the bundles of leaf, Anderson, five feet high, and his lean horse could dray from the sales floors to the packing houses where the tobacco was packed and pressed into the hogsheads or else stored for removal at a greater profit. One such packing house was converted into the Gem Dandy Garter Factory about 1915, and today three of the original five remain. One or two are still used for tobacco packing, though the season of 1936-1937 marked the hauling of immense loads of tobacco direct from the sales floors to the Winston-Salem buyers. One pack house is used as a fertilizer sales house. One loaded to the roof comb with heavily insured tobacco was mysteriously burned during the World War where such insurance collections were the fashion! Thus Anderson's dray business dwindled. Any kind of hauling he could get done, and his horses, as they died from strenuous work, would be replaced by others who in no time learned the meaning of Anderson's constant pulls on their reins and his constant and meaningful clucks. With no swivel features to his wagon, Anderson could nevertheless work the horse and wagon into any kind of close position for loading and unloading. He always said the baggage of the writer was the heaviest he carried. This was so because of books packed in the trunk or in boxes and twenty-five cents a piece was the fare!
Anderson's wife and children at home were making the acre homestead pay with cow, pigs, chickens and vegetables quickly grown on soil enriched from his dray horse stable as well as the cow stable: "snaps", tomatoes, Irish potatoes, roasting ears, butterbeans, squash in the summer, in the spring mustard and onions; in the winter "sallet" from the "seven top" and turnips, too. Fruit trees planted in time gave fruit for eating, canning and "pursurving" while all the little darkies knew where wild strawberries, crab apples and black berries grew for the picking. With Mommuh taking in white folks' washing and the dray horse money coming in, Anderson Scales prospered in Madison where he started from zero scratch. He had money in the bank.
Anderson said after "Srenduh", [HW addition: the surrender] he learned to read and write at a negro free school taught by Matilda Phillips. With his wife, Cora Dalton, sister of Sam Dalton, Anderson joined the African Methodist Church fifty years ago. This was located just across the street from the home of his former employer, Nat Wall until 1925 when it was abandoned with its parsonage and a new brick church built on the Mayodan road with stained glass memorial windows, electric lights, piano, well finished interior, and christened St. Stephen's Methodist Episcopal Church. The omission of the word "South" emphasized the fact that the members considered it a northern Methodist church as well as African. In this church, Anderson was exhorter, trustee and class leader. In then religious capacities, his education by the colored teacher, Matilda Phillips was a great help to him.
Anderson's second wife was Dinah Strong who had no children. She died December, 1933 from a goiter on her throat.