His schooling was finished when he was sixteen. His elder brothers had attended college, and he never knew exactly why he did not. But he was not fond of hard study or hard work. He lived in a sort of dreamy leisure, which seemed particularly suited to his light, airy genius, so full of humor, sunshine, and loving-kindness.
After leaving school, he began to study law in the office of a certain Henry Masterton. This was in the year 1800. He was admitted to the bar six years later; but he spent a great deal more of the intervening time in traveling and scribbling than in the study of law. His first published writing was a series of letters signed "Jonathan Oldstyle," printed in his brother's daily paper, "The Morning Chronicle," when the writer was nineteen years old.
Irving's first journey was made the very year after he left school. It was a voyage in a sailing boat up the Hudson river to Albany; and a land journey from there to Johnstown, New York, to visit two married sisters. In the early days this was on the border of civilization, where the white traders went to buy furs from the Indians. Steamboats and railroads had not been invented, and a journey that can now be made in a few hours, then required several days. Years afterward, Irving described his first voyage up the Hudson.
"My first voyage up the Hudson," said he, "was made in early boyhood, in the good old times before steamboats and railroads had annihilated time and space, and driven all poetry and romance out of travel…. We enjoyed the beauties of the river in those days.[+]
[Footnote +: Irving was the first to describe the wonderful beauties of the Hudson river.]
"I was to make the voyage under the protection of a relative of mature age—one experienced in the river. His first care was to look out for a favorite sloop and captain, in which there was great choice….
"A sloop was at length chosen; but she had yet to complete her freight and secure a sufficient number of passengers. Days were consumed in drumming up a cargo. This was a tormenting delay to me, who was about to make my first voyage, and who, boy-like, had packed my trunk on the first mention of the expedition. How often that trunk had to be unpacked and repacked before we sailed!
"At length the sloop actually got under way. As she worked slowly out of the dock into the stream, there was a great exchange of last words between friends on board and friends on shore, and much waving of handkerchiefs when the sloop was out of hearing.
"… What a time of intense delight was that first sail through the Highlands! I sat on the deck as we slowly tided along at the foot of those stern mountains, and gazed with wonder and admiration at cliffs impending far above me, crowned with forests, with eagles sailing and screaming around them; or listened to the unseen stream dashing down precipices; or beheld rock, and tree, and cloud, and sky reflected in the glassy stream of the river….
"But of all the scenery of the Hudson, the Kaatskill Mountains had the most witching effect on my boyish imagination. Never shall I forget the effect upon me of the first view of them predominating over a wide extent of country, part wild, woody, and rugged; part softened away into all the graces of cultivation. As we slowly floated along, I lay on the deck and watched them through a long summer's day, undergoing a thousand mutations under the magical effects of atmosphere; sometimes seeming to approach, at other times to recede; now almost melting into hazy distance, now burnished by the hazy sun, until, in the evening, they printed themselves against the glowing sky in the deep purple of an Italian landscape."