America’s Oldest Inn: Discover the Historic Charm of Massachusetts’ Wayside Inn

In 1716, a man named David Howe decided to become an innkeeper in Sudbury, Massachusetts. Howe converted a private residence that was built in the late 1600s into an inn known as Howe’s Tavern. Three centuries later, Howe’s Tavern—which is currently known as the Wayside Inn—is still offering cozy accommodations, piping hot meals, and a pastoral tract of land where visitors can explore several historic buildings, including a schoolhouse, a barn, and a chapel.

The Wayside Inn holds the distinction of being the oldest continuously operating inn in the United States. High-profile guests have included President George Washington, transcendentalist writer Henry David Thoreau, and poet Henry Wadsworth Longfellow. Longfellow was so taken with the Wayside Inn—known as Red Horse Tavern at the time of his visit in 1862—that he wrote a collection of poems called ‘Tales of a Wayside Inn.’ Thanks to Longfellow, the name ‘Wayside Inn’ graces the property once known as Red Horse Tavern to this day.

In addition to spending the night at the Wayside Inn, visitors can explore the historic grounds, which include several displays of colonial furniture and artifacts, an antique grist mill that produces flour available for purchase in the gift shop, and a one-room schoolhouse that was transported to the property when automobile magnate Henry Ford owned the inn. Local lore states that Mary from the nursery rhyme ‘Mary Had a Little Lamb’ was a student at the Wayside Inn’s Redstone Schoolhouse.

The Innkeeper’s Loop Hiking Trail allows visitors to explore tranquil streams, lush gardens, and stately forests. This trail is especially breathtaking in the fall when New England’s vibrant changing leaves are on display. You don’t have to be a guest at the Wayside Inn to traverse the Innkeeper’s Loop Hiking Trail and visit historic buildings such as a root cellar, a cider mill, and an ice house.

If you work up an appetite while exploring the Wayside Inn grounds, you can stop at one of the Wayside Inn’s cozy dining rooms for an English ale and a New England lobster roll. Every dining room features colonial decor, including fireplaces that always have a roaring fire during the colder months.

A trip to the Wayside Inn is an absolute must if you love places that are steeped in history. There’s a good chance that the sheer beauty of the grounds will inspire you to write your own book of poems.