Sudbury and the Wayside Inn in 2026

Drive west on Route 20 past the town line and you pass a low red building set back from the road, older than the country it sits in. Longfellow's Wayside Inn has been serving travelers since 1716, which makes it the oldest operating inn in America. I bring clients here for lunch when they're deciding whether Sudbury is home. The place tells you more about the town than any listing sheet can.

A tavern older than the republic

David Howe was granted a license in 1716 to keep a house of entertainment for travelers on the Old Boston Post Road. It ran as Howe's Tavern, then became the Red Horse Tavern after 1746. Ezekiel Howe, the third Howe to keep the place, marched two companies of Sudbury militia to Concord on April 19, 1775, when Paul Revere's alarm reached town. Sudbury itself was incorporated in 1639. So when people say this area has deep roots, they mean it literally. The town is older than the inn, and the inn is older than the United States.

The name we use now comes from Henry Wadsworth Longfellow, who visited in 1862 and published Tales of a Wayside Inn the following year.

Henry Ford's second act

By the 1920s the building was fading. Henry Ford bought it in 1923, restored it, and eventually handed it to a charitable foundation that still runs it. He didn't stop at the inn. He built the Grist Mill nearby, finished in 1929 and grinding its first cornmeal on Thanksgiving Day. He raised the Martha-Mary Chapel in 1940 from timber downed in the 1938 hurricane, and in 1926 he moved the little Redstone schoolhouse, the one from "Mary Had a Little Lamb," onto the grounds. Today the Wayside Inn Foundation stewards more than 100 acres of fields and forest around it.

What history does to a market

Here's why I raise it with buyers and sellers, not just history buffs. Land like that, protected and permanent and green, is a big part of why so much of Sudbury still feels rural even as it sits roughly 20 miles from Boston. It's part of what people are paying for.

And they are paying. Over the three months ending this spring, the median sale price in Sudbury sat near $1.1 million, up about 8 percent from a year earlier, with homes going under agreement in roughly 19 days. Zillow puts the typical home value close to $1.08 million. It's one of the more competitive markets in MetroWest, and the scarcity of developable land is a quiet reason why.

For owners already here

If you own near the historic district or one of Sudbury's conservation parcels, that setting is an asset worth naming when you sell. Buyers respond to it. And if you're weighing a renovation, homes with genuine period character, the real colonials rather than the reproductions, tend to reward careful, sympathetic updates more than gut jobs. I'm glad to walk a room with you before you make those calls.

Sudbury rewards people who want a little history in their daily life without giving up a Boston commute. The Wayside Inn is the clearest expression of that trade.

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If you're curious whether Sudbury is your next chapter, I'd love to meet you for lunch at the Inn and talk it through.

Market figures sourced from Redfin and Zillow, June 2026. Data shifts quickly; reach out for current numbers on a specific home or neighborhood.