Longfellow’s Wayside Inn: America’s Oldest Inn Review

Longfellow’s Wayside Inn is recognized as America’s oldest operating inn, and it earns that title. Meticulously restored in New England’s Sudbury, Massachusetts, it offers a comfortable night’s stay, a great meal, and historic grounds worth exploring. Just don’t worry too much about the ghosts.

longfellows wayside inn exterior at sudbury ma — Longfellow’s Wayside Inn has welcomed guests in Sudbury, Massachusetts since 1716.

History of Longfellow’s Wayside Inn

If the name sounds familiar, it should. Henry Wadsworth Longfellow wrote Tales of a Wayside Inn in the inn’s parlor back in 1863. The book’s popularity led the owner to rename the property Longfellow’s Wayside Inn in 1897. But the inn’s history stretches back long before Longfellow ever picked up a pen.

The Wayside Inn was already 160 years old when Longfellow wrote about it. Built in 1703, it started as a two-room home along the King’s Highway, the main interstate of its day, in Sudbury, Massachusetts, just outside Boston.

Originally known as Howe’s Tavern, it was granted a license to operate as an inn in 1716. The name changed more than once over the centuries, but its reputation never did: a great place to eat, drink, and rest for weary travelers and locals alike.

longfellows wayside inn old kitchen dining room at sudbury ma — Once the inn’s working kitchen, this room now serves as one of the historic dining spaces.

Longfellow’s Wayside Inn has deep historic roots in the years after Longfellow too. Automaker Henry Ford saved the inn when he purchased its roughly 100 acres and nine buildings in 1923, then poured his resources into restoring the property. Henry and his wife Clara made it their mission to preserve historic sites, including the Henry Ford Museum outside Detroit. Just before his death in 1944, Ford established the Wayside Inn Foundation to preserve the property for generations to come.

Our History With the Inn

Our first encounter with the Wayside Inn was in the 1990s. We’d been advised to reserve early and stay overnight in one of the original rooms still available to guests. Our recent visit was like a chance to revisit an old friend and take a nostalgic trip down memory lane more than three decades later.

Staying at the Inn

Longfellow’s Wayside Inn has 10 overnight rooms, but for the full experience, two matter most. Rooms 9 and 10 are the oldest, dating back to the late 18th century.

Getting to rooms 9 and 10 is part of the experience itself. A narrow, creaky staircase winds up to the two oldest rooms, the kind that feels like it belongs in the 18th century because it does. When we first stayed there, only a rope served as the railing. Today a proper handrail helps steady the climb, though the stairs still creak with every step.

longfellows wayside inn room 9 at sudbury ma — Room 9 is one of only two rooms remaining from the inn’s original 18th century structure.

Every room offers a quaint New England feel, filled with antiques and period reproduction pieces. Each features a modern king, queen, or full-size bed along with a full bath. The one thing you won’t find in any room is a TV.

What you miss out on without a TV, you make up for with the ghosts. Several rooms are reported to be haunted. We were lucky to stay in room 9, the potential home of the inn’s most famous eternal guest, Jerusha Howe. Jerusha was the sister of former owner Lyman Howe. Known as the “belle of Sudbury,” she loved to play piano at the inn and fell in love with an Englishman. He reportedly proposed, then returned to England to arrange the marriage but never came back. She died of a broken heart in 1841 and has never left room 9.

We saw no full body apparitions, but we didn’t have a restful night’s sleep either, wondering about the possibilities. Without a TV, we spent the evening reading notes tucked inside a chest, left by past guests recounting their own paranormal experiences in the room. Real or imagined, those notes made for a charming way to pass the evening.

Dinner at Longfellow’s Wayside Inn

Our recent visit back to Longfellow’s Wayside Inn was for dinner and a stroll around the historic grounds. Dining at the Wayside Inn is like stepping back in time. The low ceilings with the dark wooden beams carry you back to the early 1700s.

Each of the rooms has its own story to tell, and they have seen plenty of stories. The original rooms remain in use, including the old bar room which dates back to 1707. The inn’s old kitchen is now one of the dining rooms. The current tap room was once the Howe family’s private kitchen.

longfellows wayside inn bar at sudbury ma — The inn’s bar still shows off original wooden floors and low wood beam ceilings.

They serve lunch Wednesday through Saturday starting at 11am. They also offer a traditional Sunday roast dinner from 12pm to 7pm that is reminiscent of a London pub Sunday menu. For us, we were there for dinner which is available starting at 4:30pm Wednesday through Saturday.

If you’re hungry, the prime rib is worth considering. Served with au jus and a baked potato, it comes in two cuts: the English cut at 12 ounces or the heartier Innkeeper’s cut at 16 ounces. Every meal comes with a basket of rolls and cornbread, made with flour milled right on the property. That bread basket alone might be the best reason to write this Wayside Inn restaurant review, it was the standout bite of the entire meal.

longfellows wayside inn prime rib at sudbury ma — The Innkeeper’s cut of prime rib, served with au jus and a baked potato.

Visiting New England, it is natural to want fresh seafood. And the Wayside Inn has that covered too. We tried the New England scallops. They are baked, and served with butter and Ritz crackers crumbs. This dish was good, but was very rich with all that butter.

A less adventurous selection is the roasted chicken breast dinner. This dish is served with a cranberry cornbread stuffing. Beyond main entrees, they offered some great looking appetizers and desserts, including a

Walking the Grounds

As you plan your visit, make sure you include time in your schedule to enjoy the grounds of the Wayside Inn. We were there on a late spring afternoon with idea conditions to walk around and enjoy the ideal New England setting.

When Henry Ford took over, one of his first improvement was building the Grist Mill. The Mill is a picture postcard setting to see, and is still in operation. In the area surrounding the mill are several walking trails along side the water which were very relaxing to stroll along. It is also an area where you will find great scenery for photos.

longfellows wayside inn grist mill at sudbury ma — The Grist Mill sits on the Wayside Inn property and is part of what makes the grounds worth a walk.

Also built by Henry Ford, The Martha-Mary Chapel is also on the grounds for you to visit. The chapel is named after Ford’s mother and his mother-in-law.

In terms of historic buildings on the ground at Longfellow’s Wayside Inn, the Redstone Schoolhouse is the most historic. The schoolhouse dates back to 1798, and is believed to be the school of “Mary Had a Little Lamb” fame.

Good to Know Before You Go

The Wayside Inn sits at 72 Wayside Inn Road, Sudbury, Massachusetts, about 20 miles west of Boston. Lunch runs Wednesday through Saturday from 11:30 am to 3 pm, with dinner following from 4:30 to 7:30 pm. Sunday hours run noon to 7:30 pm. The inn is closed Mondays and Tuesdays, though select Tuesday evenings in summer host the inn’s popular Strawberry Concerts, an outdoor concert series with live music and strawberry shortcake during intermission.

That’s just one example of what the inn offers beyond a standard dinner reservation. Throughout the year, the Wayside Inn hosts special dining events like themed dinners and seasonal menus, so it’s worth checking their events calendar before you visit. You might find your trip lines up with something more than a typical night out.

Reservations for dining can be made by booking online through Resy or by calling the inn directly at 978-443-1776. Overnight stays are handled by phone only, and with just 10 rooms total, and only two of them the original historic rooms, booking well ahead is essential if you’re hoping to land rooms 9 or 10.

Parking is on-site and free, with plenty of space across the property’s 100-plus acres. The grounds are open to the public from dawn to dusk, so give yourself time before or after your meal to walk them, especially around the Grist Mill.

As a nonprofit historic site, the Wayside Inn Foundation relies on visitor support to help preserve the property, something worth knowing if you want your visit to mean a little more than just a meal.

Our return visit reminded us why the Wayside Inn has stuck with us all these years. Henry Ford’s vision to preserve this inn and its surrounding grounds still shows in every corner of the property, from the serene grist mill to the quiet trails beyond it. Staying overnight is a chance to immerse yourself in history, and maybe cross paths with a ghost or two. The food was good, though not quite as memorable as we remembered, but still a worthy dining experience when paired with everything else the property has to offer.

If you’re planning a trip to Boston, we’ve got you covered beyond just the Wayside Inn. Check out our guides to a Salem day trip from Boston, our Fenway Park tour, and walking the Boston Freedom Trail for more ways to make the most of your New England visit.