At that time he was apprenticed as a stonemason to his elder brother James, learning a trade that would support him for the rest of his life. He continued to develop literary interests and began writing poems on Scottish subjects. When Burns died in 1796, Cunningham went to see Burns's body and was a part of the funeral procession; he later wrote a valuable essay on the funerals of Burns and Byron (
London Magazine, August 1824). He also idolized Walter Scott: when
Marmion (1808) was published, Cunningham walked all the way to Edinburgh just to lay eyes on the author. After catching sight of Scott returning to his home one evening, Cunningham was satisfied and returned to Dumfriesshire. In 1806, seeking out advice and criticism, he sent some of his poems to a local minister who was respected for his learning, Reverend John Wightman. Wightman's response was only partly encouraging: he did not really approve of poetry though he thought young Cunningham was promising, and he sent him a list of books that he should read to put his education on a more solid footing--chiefly historical and religious works. Cunningham persevered, however, and managed in 1807 to get some poems printed in
Monthly Literary Recreations, edited by Eugenius Roche in London; this short-lived periodical also published some of Byron's earliest works.
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