In 1716, David Howe began what was then called a "hous of entertainment" along the Old Boston Post Road, one of the first mail routes in the country (operating since 1673). Known as Howe's Tavern, the Inn was an expansion of Howe’s own private home. Business thrived by way of the busy coach traffic to and from the cities of Boston, Worcester, and New York. Four generations of Howes operated the Inn, including Ezekiel Howe, a Lieutenant Colonial who led the Sudbury Minute and Militia to Concord center at the beginning of the Revolutionary War on April 19, 1775. Each generation expanded the Inn’s main building as business thrived. After the death of Lyman Howe in 1861, the Inn was inherited by relatives who ceased formal operation of the Inn for short overnight accommodation, but continued renting out the hall for dances and rooms for lengthier stays.
Henry Wadsworth Longfellow visited the Howe Tavern in 1862. Inspired by 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. 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. Capitalizing on the Longfellow connection, Edward Rivers Lemon purchased the Inn in 1892, renamed it “Longfellow’s Wayside Inn,” and operated it as “a retreat for literary pilgrims.”
In 1923, automobile manufacturer Henry Ford bought the Inn from Cora Lemon. Ford used his vast resources to acquire acreage, buildings, and antiquities. With the intention of creating a living museum of Americana, he expanded the property to 3,000 acres in the towns of Sudbury and Marlboro. He added buildings to the property including the one-room Redstone School (relocated onto 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). 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. In 1944, a few years before his death in 1947, Henry and Clara Ford placed the central 125-acre parcel into a non-profit trust to preserve the Inn’s historic legacy. Henry Ford was the last private owner of the Inn.
From 1944 to 1957, the Inn was governed by a Board of Trustees made up of Ford family members and their associates. In 1957, they transitioned governance to the National Trust for Historic Preservation.
In 1960, Boston-based trustees assumed responsibility for the Inn, with no further involvement or support from the Ford family, the Ford Foundation, or the National Trust. With no endowment for ongoing maintenance, the Inn had to become successfully self-sustaining in a short period of time. Since 1960, the Inn’s success is due to the dedication of local trustees committed to historic preservation of the buildings and property and to Innkeepers with sound hotel and restaurant management skills.