The Wayside Inn in Sudbury, Massachusetts, holds the title of the oldest continuously operating inn in the United States. Established in 1686 as Howe's Tavern, it has served travelers for over 335 years. The inn gained literary fame through Henry Wadsworth Longfellow's Tales of a Wayside Inn (1863) and hosted luminaries like Longfellow, Ralph Waldo Emerson, and Henry Ford (who later purchased and restored it). Today, it remains a functioning inn, restaurant, and historic landmark.