Shenstone's youth was passed under the instruction of a clergyman, from whom he received a good knowledge of the classics and a taste for the best English literature. In 1732, at the age of eighteen, he entered Oxford University. In 1745, his paternal estate, the Leasowes, devolved exclusively upon his care, and from this period his life was spent in improving its natural beauties, amusing himself with occasional compositions in prose and poetry, and cultivating the society of his neighbours and visitors. Dodsley, his friend and publisher, wrote an elaborate description of the Leasowes, which drew multitudes to inspect and admire the beauties of the place. Shenstone died in his fiftieth year, after a life, which, though free from crime, seems to have been filled up with trifles, and unadorned by the elevation, or the active benevolence of religion.
Both the moral and poetical character of his writings is generally correct, though not lofty. His Pastoral Ballad contains some fine stanzas, but his Schoolmistress is by far the best of his poetical compositions. It is a natural and pleasing sketch of some of those scenes and characters in childhood, which the mind always loves to retrace. Simplicity and artlessness of description, good sense, benevolent humour, and pathetic tenderness of feeling, are here blended together in a manner very rare and delightful.
"With all the beauties of the Leasowes in our minds," says Campbell, "it may still be regretted, that instead of devoting his whole soul to clumping beeches, and projecting mottos for summerhouses, he had not gone more into living nature for subjects, and described her interesting realities with the same fond and naive touches, which give so much delightfulness to his portrait of the Schoolmistress."