Sudbury’s Wayside Inn is still attracting visitors centuries later


By Colin McCandless, Contributing Writer 

The Wayside Inn in Sudbury, dating back to 1716, is believed to be one of the oldest inns in America.
The Wayside Inn in Sudbury, dating back to 1716, is believed to be one of the oldest inns in America.
Photo/Courtesy of the Wayside Inn Foundation

SUDBURY – The Wayside Inn in Sudbury isn’t your typical accommodation. Believed to be one of the oldest inns in America, the site was added to the National Register of Historic Places in 1973. It has been memorialized by a famous poet, operates as a nonprofit run by a foundation and was once owned by automobile magnate and industrialist Henry Ford. And that’s just for starters. 


Early history

The earliest available documentation indicates that David How launched the first iteration of the inn, called How’s Tavern, in 1716, according to Wayside Inn archivist Lauren Prescott, who has worked with the property’s foundation department since 2021. Prescott said there is also documentation showing that How’s home, which would later become the tavern, was constructed around 1702. The How family ran the inn for four generations and made numerous additions over the years.

After that fourth generation, the inn was sold at auction and became private housing, with tenants renting the building for nearly 40 years. On Oct. 31, 1862, the esteemed New England poet Henry Wadsworth Longfellow visited the inn, which he later immortalized in his popular 1863 compilation “Tales of a Wayside Inn.”

Although Longfellow only visited once, he had friends who summered there for years and their experiences inspired his collection of poems about Wayside Inn, which ironically wasn’t an inn at that time. 

Nevertheless, his work piqued people’s curiosity about Wayside. “So, even though we had tenants that were renting the building, we actually started having guests that would come visit the grounds,” explained Prescott. “And they would give tours. People could not stay at the inn. There was no food, but people were still giving history tours, which I find really interesting.”


20th century changes

The Wayside Inn in Sudbury, shown here in 1904 with electric cars passing by, underwent numerous improvements in the early 20th century.
The Wayside Inn in Sudbury, shown here in 1904 with electric cars passing by, underwent numerous improvements in the early 20th century.
Photo/Courtesy of the Wayside Inn Foundation

Edward Lemon purchased the inn in 1897 and turned it back into what it is today: a tavern. Lemon changed the name to Longfellow’s Wayside Inn. He also built the Gate House in 1913. Henry Ford bought Wayside in 1923. He owned it until 1944 and spent $3 million expanding and improving the site. “A lot of what you see when you come onto our grounds is because of the Ford ownership,” conveyed Prescott. That includes the Grist Mill, Ice House, Cider Mill and Martha Mary Chapel. “And he really envisioned this colonial village. It was his first preservation project.”

Ford ultimately converted the inn into the nonprofit that it is today, run by the Wayside Inn Foundation, to help preserve the property as a living museum of American history.  

Despite its rich history, Prescott clarified that some stories and legends surrounding Wayside are apocryphal. For instance, George Washington and Marquis de Lafayette never stayed there—they only passed by the inn. “If he had stayed here (Washington) we would have known,” asserted Prescott.  


Now a historic district

Today, the campus and grounds are known collectively as the Wayside Inn Historic District, consisting of nine historic structures and more than 100 acres.

The Wayside Inn in Sudbury’s Old Grist Mill is a popular destination for painters and photographers.
Photo/Courtesy of the Wayside Inn Foundation

Some buildings are only open on certain days or seasonally, such as the Redstone Schoolhouse and the Grist Mill. A sweet little trivia crumb to chew on: the Pepperidge Farm cookies logo is based on the Grist Mill at Wayside Inn, shared Prescott. During summertime you can enter the Grist Mill, learn about its history and observe the mill grind corn and wheat used in the restaurant’s baked goods.

The chapel is not typically open to the public, but occasionally it hosts programs and weddings.  The Cider Mill and Cooling Plant are not open to the public. The Old Barn is rented to a small business open seasonally that sells flowers, plants, artwork and local goods.

In the main house, still referred to as Longfellow’s Wayside Inn, you’ll find the restaurant, while the Gate House is home to the Foundation offices and archive. Ford established the archive in 1927 and it has grown considerably over the past century, stated Prescott.
Their biggest collection, the Wayside Inn Collection, contains records spanning the early 1700s to the present. “So, it’s constantly evolving because we’re still an inn,” said Prescott.

“Our most interesting collection is probably the How Family Collection.” Donated in 1995, it features records and objects related to the How family (the last name later changed from How to Howe), particularly those who ran the Wayside Inn, including fans belonging to Jerusha How (the eldest child of the third innkeeper, Adam Howe) and a hunting sword owned by David’s son, Col. Ezekiel How. It also entails a bill of sale for one of Ezekiel’s slaves who lived on the property.

Additionally, there is a museum exhibit and gallery room on the inn’s first floor where people can learn about its history. In 2023, they presented an exhibit on the 100th anniversary of Henry and Clara Ford purchasing the inn. Prescott is currently working on a Longfellow exhibit tentatively slated to open in spring. 


A community resource

Another unique facet of Wayside Inn is that you don’t have to dine at its restaurant or book a room to explore the tranquil property. The Innkeepers Trail loop provides walking trails for the public to stroll the grounds and observe the buildings. Scenic ponds, like Carding Mill Pond, allow public fishing. When the weather is nice, you can take a drink outside and soak up the pastoral surroundings. 

“What’s nice is our site really attracts artists,” said Prescott. “So you will see people setting up by the Grist Mill, having a picnic that they just brought from home, or they’re painting. So yeah, we really encourage people to enjoy our grounds.”

Because the inn is located on the border of Sudbury, Framingham and Marlborough, they serve people from all three communities. Summer and fall are peak times for visitors, especially leaf lookers coming to glimpse the dazzling autumn colors.

They do need to stay busy, stated Prescott, since they are not federally funded and rely on income from the inn, private donations or their membership program.


TV appearances and programming

While funding can be a challenge, the Wayside Inn has managed to promote themselves in other ways. The historic site appeared in a 2011 episode of “Ghost Adventures,” when the show filmed a Valentine’s Day special at the inn to investigate claims that the spirit of Jerusha How still resides there.

Prescott was interviewed for a 2023 episode of the PBS series “Treasures Inside the Museum,” which discussed Wayside’s museum and some of its collections.

They also offer programs throughout the year, including on April 19, when the Sudbury Companies of Militia & Minute (SCMM) march from Sudbury to Concord and Lincoln. The event reenacts and commemorates the first day of the American Revolution (April 19, 1775). SCMM then stops by The Wayside Inn for the flag-changing ceremony. 

“A lot of people do enjoy coming to the inn for that,” said Prescott.
Another popular program is the foraging walk and workshop, held twice a year during spring and fall, which wanders the grounds and teaches participants how to safely identify wild edibles. When Halloween rolls around, the inn hosts Jerusha’s Halloween Ball, a “spirited” costume party and the biggest fundraiser supporting the Wayside Inn Foundation, with over 200 attendees.  

For more information about Wayside Inn, visit



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