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America's Oldest Operating Inn, Steeped in History and Hauntings, Seeks New Custodian

  • Nishadil
  • September 20, 2025
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  • 2 minutes read
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America's Oldest Operating Inn, Steeped in History and Hauntings, Seeks New Custodian

Imagine owning a piece of American history, a place where legends were born, presidents rested, and spectral guests still linger. That dream could become a reality as Longfellow's Wayside Inn in Sudbury, Massachusetts – America's oldest operating inn – has officially hit the market with an asking price of $3 million.

This isn't just a property sale; it's an opportunity to become the custodian of over three centuries of heritage, a vibrant business, and a treasure trove of ghostly tales.

Established in 1716, Longfellow's Wayside Inn has welcomed travelers, dignitaries, and literary giants for generations. George Washington himself is rumored to have stayed within its hallowed walls, but it's the poet Henry Wadsworth Longfellow who immortalized the inn.

He penned his renowned collection, "Tales of a Wayside Inn," while residing here, forever cementing its place in American literature. Every creaking floorboard and flickering gaslight whispers stories of bygone eras.

But the inn's allure isn't solely in its historical significance; it's also famously haunted.

The most prominent resident ghost is said to be Jerusha Howe, the sister of a former innkeeper, whose benevolent spirit is often reported wandering the halls, particularly in what was once her bedroom. Guests and staff alike have recounted encounters with a mysterious "woman in white," inexplicable cold spots, and disembodied voices, adding a thrilling layer of supernatural mystique to this already captivating establishment.

The current owners, the Sudbury Foundation, have managed the inn as a non-profit entity since 1958.

Their decision to sell stems from a strategic shift to focus on their core mission of local philanthropy. However, they are committed to finding a buyer who will preserve the inn's unique character and ensure its continued operation as a public trust. This isn't just a building; it's a living museum, a functioning restaurant, a charming lodge, and a popular venue for events, all generating robust annual revenue.

For $3 million, the buyer won't just acquire an inn; they'll inherit a sprawling 100+ acre estate.

The property boasts a fully operational grist mill, a picturesque chapel, and the iconic Redstone Schoolhouse – a historic structure relocated from Sterling, Massachusetts, that once educated the children of Henry Ford's employees. It's a complete historical village, offering immense potential for hospitality, tourism, and educational ventures.

Nancy S.

Gould of Coldwell Banker Realty holds the exclusive listing, noting the widespread interest from both private individuals and organizations eager to safeguard such a unique cultural asset. Whether you're a history enthusiast, a paranormal investigator at heart, or a visionary entrepreneur looking for an unparalleled investment, Longfellow's Wayside Inn offers an extraordinary blend of historical depth, ongoing business potential, and a touch of the beautifully eerie.

This is more than a purchase; it's an invitation to become part of America's enduring story.

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