Though times were hard and money scarce there was, in the community, a healthy appreciation of the cultural side of life. George Carter of Oatlands advertises the services of a professor of music, seemingly brought into the county by him, who "now offers to teach the fundamental rules of this science in 8 lessons so as to enable those who are taught by him, to pursue their studies by themselves until they may obtain a perfect practical knowledge of musick."[136] Music seemed to have been in the air. Eighteen months later, there is notice given by Henry Krebs that he has commenced teaching the piano and German flute and the French language. He could be found at Mrs. Peers' boarding house.[137] Lectures on English grammar are announced by E. Hazen at the house of Mrs. McCabe[138] and Charles Weineder, a miniature painter, came to Leesburg for two weeks to take orders in his art.[139]

The profession of the law was followed in Leesburg by Richard Henderson, Burr William Harrison, L. P. W. Balch (who was also secretary of the school board) and John K. Mines. Dr. J. Clapper practiced medicine at Hillsboro "where he may be found at Mr. Hough's tavern," we trust not indicating undue conviviality of the gentleman's disposition. There was ample accomodation for travellers, their servants and horses. Enos Wildman announced that he had lately acquired the Eagle Tavern, formerly run by W. Austen;[140] while Samuel M. Edwards presided at the "Leesburg Hotel & Coffee House" which he had recently purchased from Mr. H. Peers and which was "situated on the main street leading from Winchester to Alexandria, George Town and the City of Washington." Yet another tavern was operated by one "Mr. Foley" and, as we have seen, there were boarding-houses as well. Their bars were stocked without difficulty, for Lewis Mix & Co. had a distillery near the mouth of Sugar Land Run and called for rye, corn and oats.

But perhaps the most impressive picture painted by these old advertisements is that of the teeming industrial and commercial life of the town. It was still, happily, the age of the handicraftsman; the machinery age was yet to come. Transportation was uncertain and slow, and country towns largely produced the furniture, tools, clothing and other needed articles for their own inhabitants and those of their surrounding communities. The variety of the activities of the artisans and merchants of the Leesburg of that day paralleled those of other similar towns throughout the nation. John Carney had a "Boot & Shoe manufactory" which was conveniently located "on King street, next door to Messrs. Humphreys and Conrad and immediately opposite the Court House." In advertising his wares, he added that he wished to take on two or three apprentices of from thirteen to fifteen years of age. He had a business rival in William King, who conducted a similar activity and confidently announced that he had "some of the first rate workmen in the State."

Hats were made and sold by Jacob Martin "at his shop opposite the market house" who duly proclaimed "a very large assortment of hats on hand from the first quality to those of lowest prices; including a large assortment of Good Wool Hats, likewise some Morocco Caps."

If the Loudoun citizen of President Monroe's day needed the services of a tailor, they were made available by Thomas Russel whose business apparently flourished; for he advertised for "one or two journeymen taylors to whom constant employ and the best wages will be given." He also sought one or two apprentices to learn his craft.

Jonathan C. May was opening a dry goods and clothing shop under charge of D. Carter, next to the drug store of Robert R. Hough. As a competitor he had Joseph Beard with his "General and Seasonable assortment of Dry Goods" and Daniel P. Conrad who, "at the Stone House opposite the Court House" offered "a seasonable supply of Fall Goods"; he and George Richards meanwhile publishing notice of the dissolution of their former partnership. In nearby Waterford, B. Williamson and C. Shawen also dissolve their partnership in a general store, on account of Williamson moving to Baltimore and Shawen carries on under the name of C. Shawen & Co.

Samuel Tustin was engaged in a coachmaking business in Leesburg and sought "good tough white ash plant and timber—also a quantity of poplar half inch plank." He, too, wanted an apprentice, seeking one who was fifteen to seventeen years old. There was no lack of opportunity to earn a living offered to a steady lad with an inclination to work and a taste for trade. To the more mature, Aaron Burson offered to rent his fulling mill and dwelling house near Union, describing them as being in "an elegant neighbourhood for the fulling business."[141] John B. Bell, occupying a part of William Drish's house on King Street, was a bookbinder. Not daunted by the slump in business, James G. Jones and Company notify the Loudoun public that they have commenced the brush making business "at Mr. Wetherby's stone house, King Street, nearly opposite Mr. Murrays and that they want a large quantity of hog's bristles" for which a liberal price will be given "IN CASH."

S. B. T. Caldwell advertised for sale writing paper, wrapping paper and medium printing paper.

The present day collectors of old furniture will note that David Ogden had removed his business to the southeast corner of King and Cornwall Streets where he had on hand and offered "some fashionable sideboards, Eliptic Dining Tables, Secretary, Bureaus etc., etc., which I will dispose of on moderate terms. Orders from the adjacent country will be thankfully received." In the same year of 1818, Jacob and Isaac Thomas of Waterford announced that they had on hand a general assortment of Windsor and fancy chairs and were also prepared to do "house, sign and fancy painting with neatness and dispatch."