When Henry Wadsworth Longfellow rode out to Sudbury in 1862, he sized up the tavern in one line: "a rambling, tumble-down building, two hundred years old; and till now in the family of the Howes." He had the age right. The building had been licensed as Howe's Tavern back in 1716, and the same family had run it ever since. What Longfellow never saw, because it did not exist yet, was the red-shingled grist mill that now shows up in nearly every photograph anyone takes of the property. That mill was 67 years from being built.
The Mill Longfellow Never Saw
The grist mill on the property today was built by Henry Ford, starting in 1925 and finishing in 1929. It replaced an older mill that had stood on nearly the same spot since the early 1700s but had fallen apart by the time Ford bought the inn. His version produced its first ground cornmeal on Thanksgiving Day, 1929, which makes it 97 years old this year, not three centuries. It still runs. The corn and wheat ground inside go into the bakery at the inn and get sold at the gift shop and the mill itself, and the building has become one of the more photographed structures in the country, showing up on calendars nationwide. It's often described as the same mill pictured on the Pepperidge Farm label, a nod to the years the company actually sourced its flour from here.
If you have ever pulled over on Route 20 to take a picture of that mill assuming you were photographing something from the 1700s, you were photographing something built the same decade as the stock market crash.
What Ford Actually Built, and What Was Already There
Sorting the property by century clears up a lot. Standing before Ford ever arrived:
- The inn itself, licensed as a tavern in 1716
- The Redstone Schoolhouse, built in 1798, believed to be the same one-room school tied to the "Mary Had a Little Lamb" story
- The Old Barn, built in the early 1800s by the How family
Added during Ford's ownership in the 1920s and 30s:
- The Grist Mill, 1925 to 1929
- The Cider Mill, 1930, built to house a press for the apple harvest
- The Ice House, also from the 1930s, used to store ice cut from the property's ponds
- The Martha-Mary Chapel, 1940, named for Ford's mother and mother-in-law
Ford wanted the whole property to read like a working model of preindustrial New England. He ran a trade school out of the Old Barn, the Wayside Inn Boys School, from 1928 to 1947, built on the idea that people learn by doing. He put a reported $1,616,956.11 into the project. He never finished the fuller version of that vision here. He shelved it in Sudbury and later built it out properly at Greenfield Village in Dearborn, Michigan, before selling the Wayside property in 1945.
The Room You're Eating In Isn't Original Either
On the night of December 22, 1955, a fire gutted the inn and destroyed much of the antique collection Ford had assembled in the 1920s. The building reopened in June 1958 after a rebuild funded by a $500,000 Ford Foundation grant, using original beams and surviving furniture wherever they could. The reopening had its own bit of staging: a parade of antique vehicles led by a colonial stagecoach, carrying officials from the National Trust for Historic Preservation and the Ford Foundation up to the front door.
So the property carries two identities at once. There's the real colonial thread, the 1716 tavern, the 1798 schoolhouse, the early 1800s barn, and the Howe family itself, including Ezekiel Howe, who took over as innkeeper and fought with the Sudbury Minutemen during the Revolutionary War. And there's the mid-20th-century reproduction layered on top of it: Ford's mill, chapel, cider press, and ice house, plus a dining room that is itself a careful 1958 reconstruction.
Two Saturdays, Two Different Centuries
This fall the property runs its two signature events one week apart, and each one leans hard into one side of that split identity.
| Event | Date | Leans Toward | What's Actually Happening | Good For |
|---|---|---|---|---|
| Colonial Faire & Muster of Fife and Drum | Saturday, September 26, 2026 | The real 1700s | A colonial encampment, militia demonstrations, traditional crafts, fife and drum music, and a parade | Anyone curious about the Howe family and the Sudbury Minutemen connection |
| Apple Fest Family Day | Saturday, October 3, 2026 | Ford's 1920s reproduction | Hayrides, a petting zoo, craft and artisan vendors, and food, staged around the same working grist mill and cider mill Ford installed for harvest season | Families with young kids, and anyone who wants to watch the cider mill actually running |
The Faire is built around demonstrations connected to real militia history rather than generic costume theater. The Apple Fest, by the Wayside Inn Foundation's own description, is its biggest family event of the year, drawing thousands, and it's free to the public. The irony is that the more "colonial" of the two Saturdays, at least visually, with hayrides and a working cider press, is the one that's actually leaning on Ford's 1920s fantasy of colonial life. The Faire, with its muster and its militia drills, is the one closer to what was happening on this exact ground 250 years ago.
Either Saturday, the Mill Is Running
The Grist Mill is open to the public Wednesday through Sunday, 9am to 5pm, from mid-April through mid-November, so it's operating on both event Saturdays and on any ordinary fall weekend before the season closes for the year. The wider grounds, more than 100 acres of meadow, forest, and ponds, stay open to the public for walking during daylight hours through an arrangement with Sudbury Valley Trustees, though trail access can be restricted during ticketed events, so it's worth checking before you park near the encampment on Faire day.
If you're only doing one Saturday, the choice comes down to which century you'd rather spend an afternoon in. If you want to see a fife and drum muster and understand why the militia demonstrations aren't just costumes but connected to a family that actually served, September 26 is your day. If you want cider pressed in front of you, a hayride, and a petting zoo for the kids, October 3 delivers Ford's version of the same harvest, built from scratch a century after the fact but running exactly as intended.
Either way, the mill wheel you'll photograph is turning on a building that's been open for less than a hundred years, telling a story about a place that's been here for more than three hundred. That gap is the whole point of the property, and it's worth knowing before you show up with your camera.
Rutledge Properties keeps track of what's actually worth a Sudbury Saturday because we live and work in this town too, not because there's a listing at the end of it. If a fall walk through Wayside Inn's grounds ever turns into a longer conversation about the neighborhood around it, Rutledge Properties is easy to find.
