A good story is told of the young cadet which shows his ability, even at this time, to make the best of circumstances apparently untoward, and to turn to his advantage his surroundings, whatever they might be. Having been for some slight breach of discipline required to bestride a gun in the campus for a short time, he saw, to his dismay, coming down the walk the beautiful daughter of Dr. Foster Swift, a young lady who, visiting West Point, had taken the hearts of the cadets by storm, and who, little as he may at the time have dreamed it, was destined to become his future wife. Pulling out his handkerchief, he bent over his gun, and appeared absorbed in cleaning the most inaccessible parts of it with such vigor as to be entirely unaware that any one was passing; nor did the young lady dream that a case of discipline had been before her until in after years, when, on a visit to West Point, an explanation was made to her by her husband.

It was at this time of his life that the refinement and taste for which Major Whistler was ever after noted began to show itself. An accomplished scientific musician and performer, he gained a reputation in this direction beyond that of a mere amateur, and scarcely below that of the professionals of the day. His sobriquet of "Pipes," which his skill upon the flute at this time gave him, adhered to him through life among his intimates in the army. His skill with the pencil, too, was something phenomenal, and would, had not more serious duties prevented, have made him as noted an artist as he was an engineer. Fortunately for the world this talent descended to one of his sons, and in his hands has had full development. These tastes in Major Whistler appeared to be less the results of study than the spontaneous outgrowth of a refined and delicate organization, and so far constitutional with him that they seemed to tinge his entire character. They continued to be developed till past the meridian of life, and amid all the pressure of graver duties furnished a most delightful relaxation.

Upon completing his course at the Military Academy he was graduated, July 1, 1819, and appointed second lieutenant in the corps of artillery. From this date until 1821 he served part of the time on topographical duty, and part of the time he was in garrison at Fort Columbus. From November 2, 1821, to April 30, 1822, he was assistant professor at the Military Academy, a position for which his attainments in descriptive geometry and his skill in drawing especially fitted him. This employment, however, was not altogether to his taste. He was too much of an artist to wish to confine himself to the mechanical methods needed in the training of engineering students. In 1822, although belonging to the artillery, he was detailed on topographical duty under Major (afterward Colonel) Abert, and was connected with the commission employed in tracing the international boundary between Lake Superior and the Lake of the Woods. This work continued four years, from 1822 to 1826, and subsequent duties in the cabinet of the commission employed nearly two years more.

The field service of this engagement was anything but light work, much of it being performed in the depth of winter with a temperature fifty degrees below zero. The principal food of the party was tallow and some other substance, which was warmed over a fire on stopping at night. The snow was then removed to a sufficient depth for a bed, and the party wrapped one another up in their buffalo robes, until the last man's turn came, when he had to wrap himself up the best he could. In the morning, after warming their food and eating, the remainder was allowed to harden in the pan, after which it was carried on the backs of men to the next stopping place. The work was all done upon snow-shoes, and occasionally a man became so blinded by the glare of the sun upon the snow that he had to be led by a rope.

Upon the 1st of June, 1821, Whistler was made second lieutenant in the First Artillery, in the reorganized army; on the 16th of August, 1821, he was transferred to the Second Artillery, and on the 16th of August, 1829, he was made first lieutenant. Although belonging to the artillery, he was assigned to topographical duty almost continually until December 31, 1833, when he resigned his position in the army. A large part of his time during this period was spent in making surveys, plans, and estimates for public works, not merely those needed by the national government, but others which were undertaken by chartered companies in different parts of the United States. There were at that time very few educated engineers in the country, besides the graduates of the Military Academy; and the army engineers were thus frequently applied for, and for several years government granted their services.

Prominent among the early works of internal improvement was the Baltimore & Ohio Railroad, and the managers of this undertaking had been successful in obtaining the services of several officers who were then eminent, or who afterward became so. The names of Dr. Howard, who, though not a military man, was attached to the Corps of Engineers, of Lieut.-Col. Long, and of Capt. William Gibbs McNeill appear in the proceedings of the company as "Chiefs of Brigade," and those of Fessenden, Gwynne, and Trimble among the assistants.

In October, 1828, this company made a special request for the services of Lieutenant Whistler. The directors had resolved on sending a deputation to England to examine the railroads of that country, and Jonathan Knight, William Gibbs McNeill, and George W. Whistler were selected for this duty. They were also accompanied by Ross Winans, whose fame and fortune, together with those of his sons, became so widely known afterward in connection with the great Russian railway. Lieutenant Whistler, says one who knew him well, was chosen for this service on account of his remarkable thoroughness in all the details of his profession, as well as for his superior qualifications in other respects. The party left this country in November, 1828, and returned in May, 1829.