Longfellow’s Wayside Inn

Set alongside an old stagecoach road, Longfellow’s Wayside Inn is the focal point of the Wayside Inn Historic District in Sudbury, Mass.

It began as a home for the How family in 1707, until they received a license in 1716 to make it a “house of entertainment.” This enabled them to provide rooms, meals and drinks for travelers passing by on Old Boston Post Road, a route that connected Boston to towns west.

Featuring eight guest rooms, two historical guest rooms and ten dining and function rooms, the Wayside Inn has been operational for more than 300 years. It is the oldest operating Inn in the United States. Three period-style dining rooms round out the place, including the parlor where Henry Wadsworth Longfellow penned his work, Tales of a Wayside Inn. It also showcases historical items.

“Inspired by stories of Howe family hospitality shared with him by his colleagues and friends, Daniel Treadwell, Luigi Monti, Henry Wales, and Thomas W. Parsons, all of whom were regular summer residents of Howe’s Tavern; and the coziness of the Inn’s atmosphere and pastoral landscape, Longfellow wrote a series of poems focused on a group of fictitious characters that regularly gathered at the old Sudbury tavern,” according to the official website. “The poems were published in 1863 as the Tales of a Wayside Inn. Innkeeper Lyman Howe was the inspiration for The Landlord’s Tale, more widely known as The Midnight Ride of Paul Revere. The Tales of a Wayside Inn brought the Inn to a level of national significance.”

The inn changed ownership and was renamed Longfellow’s Wayside Inn to capitalize on the attention. It changed hands a few more times, and was acquired in 1923 by industrialist Henry Ford, who added acres, buildings and antiquities to the property.

“From 1928–1947, Ford operated the Wayside Inn School for Boys, a trade school that prepared indigent boys for potential employment in Ford’s factories,” the website says. “In 1944, a few years before his death in 1947, Henry and Clara Ford placed the central 100+acre parcel and nine buildings into a non-profit organization to preserve the Inn’s historic legacy. Henry Ford was the last private owner of the Inn.”

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