With humble beginnings in 1716 as a simple, two-room family home hosting travelers along the Old Boston Post Road in Sudbury, Massachusetts, Longfellow's Wayside Inn is now the oldest inn operating in the United States. It is also one of few extant colonial taverns where locals and travelers can still enjoy a pint of ale — although the food and beverage options have vastly expanded since the building's construction. Nestled under great oak trees at the center of a majestic 100+ acre property, the Inn offers generous hospitality, delicious New England cuisine, and comfortable lodging in a warm, historic setting radiating with charm.

The Inn was known as Howe's Tavern until 1746 when Ezekiel Howe, the third generation of the Howe family to operate the Inn, renamed it The Red Horse Tavern. Howe led two companies of Sudbury militia to Concord in answer to Paul Revere's alarm on April 19, 1775 and later served as Colonel of the Fourth Middlesex Regiment under George Washington. After the war, Howe continued to operate the tavern until his death in 1796.

Henry Wadsworth Longfellow visited Howe Tavern in 1862 and consequently wrote a series of poems focused on a group of fictitious characters that regularly gathered there. Published in 1863 as Tales of a Wayside Inn, they brought the Inn to a level of national significance.

In 1923, automobile manufacturer Henry Ford bought the Inn using his vast resources to acquire acreage, buildings, and antiquities with the intention of creating a living museum of Americana. He expanded the property to almost 3,000 acres and added buildings to the property, including the one-room Redstone Schoolhouse (relocated to the property in 1925), a fully functioning Grist Mill (built in 1929), and the Martha-Mary Chapel (built in 1940 from trees felled in the historic Hurricane of 1938).

Before his death in 1947, Henry and Clara Ford placed the central 100+ acre parcel and nine buildings into a non-profit organization, now The Wayside Inn Foundation, to preserve the Inn's historic legacy. Henry Ford was the last private owner of the Inn.

Built in 1703, The Wayside Inn is considered the oldest working inn in the United States. It began as a simple two room home, located on what was the King's Highway, which was the main route heading west from Boston and south to Hartford and New Haven, Connecticut. An official license was granted by the Sudbury selectmen to David Howe “to keep a house of entertainment for travelers” in 1716. His son, Ezekiel Howe, was the next innkeeper and fought in the Revolutionary War with the Sudbury Minutemen. Over the years the Howes made considerable changes and additions to the building.

In 1862, the poet Henry Wadsworth Longfellow visited the inn with his publisher James T. Fields shortly after it had become the Red Horse Tavern. He noted it was “a rambling, tumble-down building, two hundred years old; and till now in the family of the Howes”.[3] He soon put together a compilation of poems called Tales of a Wayside Inn; it was published in 1863.

Although the Inn is best known for Colonial history and its association with Longfellow, there is a Thoreau connection; he is known to have visited the Inn once, on May 22, 1853, with his friend and walking companion Ellery Channing.

Known as the Red Horse Tavern at the time, Thoreau called it the “Howe Tavern”. He and Channing chatted with “an old woman” who was 91 years old, telling the two men that it was “the first house built on the spot”. Thoreau also noted the Tavern sign: “the oldest date on the sign is ‘D.H. 1716′”. The innkeeper at the time was Lyman Howe and the old woman told Thoreau that she'd been “a servant”.

Leaving their horse and carriage at the inn, Thoreau and Channing walked to nearby Nobscot Hill. It was, Thoreau noted, “the best point from which to view the Concord River valley”. From there they could see Wayland, Norton, Berlin, Massachusetts and the Harvard hills to the west.

Today, Longfellow's Wayside Inn is a charming hotel and restaurant. Nobscot Hill can still give the great views that Thoreau and Channing had, but much of the area is now built up with expensive homes. Some of it has been preserved however; Nobscot Conservation Land is 118 acres of woodland, meadows, Native American and colonial historic sites, and an abandoned apple orchard. Surrounding the hill are other large parks and parcels of conservation land, including Callahan State Park (958 acres), the Sudbury Weisblatt Conservation Land, and Wittenborg Woods (83 acres). All are connected by various hiking trails, including the Bay Circuit Trail.

This site is included on the itinerary Following in Thoreau's Footsteps: Exploring the Freedom's Way National Heritage Area created by The Thoreau Society with support from the Freedom's Way National Heritage Area Partnership Grants Program.