His first experience in journalism was as editor of the _Tablet_ in Boston, May 19, 1795. The paper lived just thirteen weeks.
Dennie next tried his Bohemian fortunes in Walpole, N. H., and contributed to the _Farmer's Weekly Museum_, a good and popular journal that had been founded in 1790, the papers entitled "The Lay Preacher," upon which rests his literary fame. Of this magazine he became editor in 1796, and at once gathered about him a number of noble swelling spirits who contributed racy and original reading to the "Farmer's" subscribers.[10]
[10] Dennie always remained faithful to his New England friends. T. G. Fessenden had been one of the contributors to the _Farmer's Museum_; when his "Terrible Tractoration" appeared, Dennie wrote to the _Port Folio_, "To Connecticut men studious either of Hudibrastic or solemn poetry, we look with eager eyes for the most successful specimens of the inspiration of the Muse." Fessenden was the last to maintain the fame of the "Hartford Wits;" and the glory of "McFingal," and "The Conquest of Canaan" and the "Anarchiad," and the "Political Green house" and "The Echo" faded with the failing of the _Farmer's Museum_.
The publisher became bankrupt in 1798, and Dennie pilgrimaged to Philadelphia, without fortune and without a patron. His service under Pickering was of short duration.
In connection with Asbury Dickins, a son of John Dickins of the _Methodist Magazine_, he began, January 3, 1801, the publication of the _Port Folio_, by Oliver Oldschool, Esq., the best of Philadelphia magazines, which he continued to edit until his death, in 1812. Dennie's strong personality and engaging qualities of mind and heart attracted attention, and made him many friends. With genuine editorial tact and skill he drew to himself all the literary ability of the city, which was then "the largest and most literary and most intellectually accomplished city in the Union," to quote the words of a later editor of the _Port Folio_, Dr. Charles Caldwell. There was scarcely a more picturesque figure in Philadelphia in the first decade of this century than that presented by the editor of the _Port Folio_. It would be necessary to go to London and to Oliver Goldsmith to find another to outshine this Oliver Oldschool as Buckingham saw him slipping along Chestnut Street to his office "in a pea-green coat, white vest, nankeen small-clothes, white silk stockings and pumps, fastened with silver buckles which covered at least half the foot from the instep to the toe." Dennie was but 44 years of age when he died; Buckingham says he was "a premature victim to social indulgence." Those were the days of hard drinking and of high thinking. Nothing so frugal as a cup of Madeira and a cold capon's leg would satisfy Dennie's epicurean soul. He was a social creature, and those _noctes ambrosianæ_ of the Tuesday Club when Tom Moore, who celebrated the club in his eighth epistle, or some other lover of Anacreon was the guest, were often kept up until it was too late to go to bed. Wine songs and Martial-like epigrams of pointed indecencies are correspondingly brisk and plentiful in the pages of the _Port Folio_.