Insuring The Story of Longfellow's Wayside Inn

Insuring The Story of Longfellow's Wayside Inn

Having been around for over 300 years, Longfellow’s Wayside Inn is the oldest operating inn in the United States. The inn is located in Sudbury, Massachusetts and was opened by David How in 1716; the inn was originally named How’s Tavern. How started the inn as an expansion of his own home where people often stayed when traveling to and from cities such as Boston, Worcester and New York. The inn was passed down through the How family until the last How passed away in 1861. For the next 30 years, How’s Tavern served as a homestead and boarding home for farmers and temporary guests.

In 1862 Henry Wadsworth Longfellow, a famous poet, visited the old How Tavern. Longfellow found inspiration at the inn and made the tavern the gathering place for his characters in his 1863 book Tales of a Wayside Inn. Longfellow’s first printing sold out within a single day. Because of the immense popularity of the poet and his book, generations of people would seek out to visit How’s Tavern.

In 1896, Edward River Lemon, a wealthy man from Malden, purchased the How property. Lemon wanted the inn to become a summer retreat that focused on its artistic and literary history. Lemon renamed How’s Tavern to Longfellow’s Wayside Inn. He wanted the inn to be a place of culture where artists and other professionals could gather. He even had the Society of Colonial Wars to gather at the inn in 1897, where Samuel Arthur Bent gave his speech ‘The Wayside Inn – Its History and Literature.’ In addition, groups such as The Paint and Clay Club met regularly at the Inn to find inspiration. Around 1900, Lemon created an English garden in remembrance of Longfellow that had a copy of Westminster Abbey that depicted Longfellow himself.

Henry Ford purchased the Inn in 1923 and had the plan to transform it into a living museum of American history as well as continue to operate as a hotel and restaurant. Ford said in an interview for the New York Times that some of his motivation to buy the property came from his love for Longfellow. Ford purchased 3,000 acres around the property and added eight new buildings including The Grist Mill, a school for children, and the Wayside Inn School for Boys, which trained boys to become employees of his Michigan factories. Henry Ford brought international significance to the inn which brought in visitors such as Calvin Coolidge and Charles Lindbergh. Ford also had an annual retreat at the inn with his friends Harvey Firestone, Thomas Edison and John Burroughs called the ‘Vagabond’ retreat.

Henry Ford and his wife Clara, preserved the original inn by placing the 125-acre parcel into a non-profit trust. When Ford died, his family served as the board of governance for the property. The family sold most of the 3,000 acres and secured the preservation of the property by placing 50-year development restrictions on each parcel sold. When a devastating fire occurred in 1995, most of the inn was destroyed and the Ford family hired architects and historic preservationists to restore the building. After the fire, the Ford family decided to transition the governance to the National Trust of Historic Preservation.

The Inn went on to become successful and is still a popular tourist destination today. The inn became a Local Historic District in 1967, a Massachusetts Historic Landmark in 1970 and a National Register District in 1973.


For more information about Longfellow’s Wayside Inn visit their website at


This blog is a part of our Insuring The Story Project, where we are featuring some of our clients who have interesting stories behind their historic property. If you’re one of our clients and think your property is worth writing about, please email us at