Victorian Innkeeper Edward Lemon desired guests of a more cultural bent to visit his country refuge, encouraging actors, artists, students, and professional people.
The Paint and Clay Club, a group artists, poets, and writers which included Alfred T. Ordway (1819–1897), Abbott Fuller Graves (1859–1936), Edward Filene, and Quincy Kilby, met regularly at the Inn. Lemon displayed his own art collection as well as that of Club members in a special gallery he had built (now the Ford Room).
Around 1900, Edward Lemon created the ultimate homage to Longfellow—an English country garden named for the poet, complete with a copy of the Westminster Abbey bust depicting Longfellow himself. Many artists outside the circle of the Paint and Clay Club ventured to the Wayside Inn for inspiration.
Longfellow's "Prelude" to the Tales connotes an appreciation for a vanishing countryside and a disappearing way of life, which echoed the sentiments conveyed by painters of the Hudson River School. Almost immediately after the publication of the Tales, well-known and established artists such as Thomas Hill (1829–1908) and Childe Hassam (1859–1935) came to the Wayside Inn to paint its rural landscape.
Printmakers Currier & Ives (1857–1907) produced two large-folio renditions of the Wayside Inn, one in 1867 titled "Eventide October" which was based upon a stunning oil painting by B. Hess (very little about whom is known).
Landscape artists Edmond Henry Garrett (1853–1929) and Albert Fitch Bellows (1829–1903) created vivid etchings of the old How(e) homestead in the late 1880s, testimony to the enduring quality of Longfellow's 1863 book of poems. Countless amateur painters also drafted canvases which showed an aging inn and tavern, further recognition of the far reaching sentiment created by Longfellow's writing.