Every good spy story has a room where the plotting happens — and a road that gets the message out of it. Setauket, another chapter in this series, was the room. Smithtown, St. James, and Kings Park were the road, the river crossing, and, years later, the place where the general himself stopped to rest his horses and say thank you.

That distinction matters, and it's worth being honest about it up front. Abraham Woodhull, Anna Strong, and the rest of the Culper Spy Ring did their covert work out of Setauket, roughly ten miles to the east. Nobody in Smithtown, St. James, or Kings Park was passing coded letters to Robert Townsend in Manhattan. Their role in this story is a different kind, and in some ways a more universal one: they were the connective tissue. The stretch of road, farmland, and shoreline that made the whole operation geographically possible, and later, the ground George Washington chose to walk when the war was over and it was time to thank the people who had helped him win it.

A Secret Courier's Route, Retraced by a President

Start with the mechanics of the Culper Ring, because they explain everything that follows. Major Benjamin Tallmadge built the network in late 1778 at Washington's request, and its lifeblood was a single courier: Austin Roe, a Setauket tavern keeper who rode roughly fifty-five miles round trip to Manhattan to collect intelligence from Robert Townsend's coffeehouse and carry it home. That ride didn't happen in a vacuum. It followed the old North Shore roads that ran west out of Setauket, through the farmland and crossroads that would one day become downtown Smithtown, St. James, and Kings Park, before continuing on toward the ferries that crossed to the city.

Roe never wrote his route down for obvious reasons, so we can't hand you a mile marker. But we do know that eleven years later, in April of 1790, President Washington traveled this same North Shore corridor on a goodwill tour of Long Island, and he chose it deliberately, tracing westward from Setauket the way his courier once had. His own diary records the stop that followed.

Widow Blydenburgh's Tavern, Ten Miles from Setauket

Leaving Setauket early on the morning of April 23, 1790, Washington's party stopped in Smithtown to rest and feed the horses at an inn he described in his diary simply as a "decent House," run by a widow named Blydenburgh. The tavern itself is long gone, but its stone doorstep still exists today — a small, almost stubborn survivor of a morning when the sitting president of the United States paused in what was, at the time, a quiet farming crossroads.

It's a small moment in the larger sweep of the Revolution, but it's the kind of detail that rewards patience. A doorstep doesn't announce itself as historic. It just sits there, outlasting the building around it, waiting for someone to ask what happened on top of it.

The Woodhull Family Comes to Smithtown

There's a second, quieter thread connecting this stretch of the North Shore to the ring, and it runs through family rather than road. Washington's carriage that same April morning passed a house on what's now West Main Street in Smithtown, built around 1752 and known today as the Arthur House. Decades later, it became home to Mary Woodhull Arthur — the daughter of Abraham Woodhull himself, the Setauket farmer who ran the ring under the alias "Samuel Culper Sr."

Woodhull spent the war years in constant, well-founded fear of being unmasked. It's a fitting quiet coda that a generation later, his own daughter would settle into ordinary small-town life along the very corridor her father's secret letters had once traveled through.

Named for a Bull, Settled Well Before the Revolution

Smithtown's own origin story predates the Revolution by more than a century, and it's worth a short detour because it explains why the town existed at all by the time the war arrived. Local legend holds that Richard "Bull" Smith, who founded the settlement in 1665, secured his land grant by riding a bull around the boundary of everything he wished to claim in a single day. True or embellished, the story stuck, and so did the name.

By the time of the Culper Ring, Smithtown was already a settled, working farm community more than a century old — exactly the kind of established, unremarkable place a courier could pass through without drawing much notice. Anonymity, as it turns out, is its own kind of usefulness.

St. James and Kings Park: Farmland That Became Parkland

East and north of downtown Smithtown, the hamlets of St. James and Kings Park hold the pieces of this landscape that have survived best, mostly because so much of it was later set aside as public parkland rather than developed. The Obadiah Smith House in Kings Park, built around 1708 by Bull Smith's own grandson, still stands on St. Johnland Road and is preserved today as a house museum. It's about as close as this corridor gets to a building that would have looked entirely familiar to anyone riding through in 1778.

The rivers and woodlands here tell the same story from a different angle. The Nissequogue River, which threads through Kings Park and St. James on its way to Long Island Sound, would have been a working waterway in the eighteenth century — a source of mills, fish, and transportation, not the recreational kayaking route it is today. Much of its watershed is now protected within Nissequogue River State Park and Caleb Smith State Park Preserve, which means the woods and wetlands you'd walk through now are genuinely closer to what Washington's contemporaries saw than almost anything you'd find in a more developed part of the Island.

The Culper Ring's real advantage was never secrecy alone. It was geography — a road ordinary enough that nobody thought to watch it.

On the North Shore corridor, Washington's Spy Trail

A Family Name That Outlasted the Building

Even where the original structures are gone, the names tend to linger. Blydenburgh County Park, just south of downtown Smithtown, carries the same family name as the widow who fed Washington's horses in 1790. Its preserved millpond and grist mill site aren't the exact tavern he stopped at, but they capture the same working, mill-and-farm economy that defined this part of the North Shore for the better part of two centuries — colonial roots that outlasted the buildings themselves.

Setauket's Hub, and This Corridor's Different Job

It helps to see the two roles side by side, because they were genuinely different jobs, and both were necessary.

A Landscape Worth Slowing Down For

What strikes me most about this stretch of the trail isn't any single building — it's how much of the surrounding land has been protected rather than paved. Caleb Smith, Nissequogue River, and Sunken Meadow State Parks together preserve thousands of acres of the exact river valley, woodland, and shoreline that shaped daily life here in the 1770s and 1780s. Walk any of those trails on a quiet weekday morning, and you're seeing something close to what Austin Roe would have passed on his ride, or what Washington's carriage rolled by on its way to Widow Blydenburgh's door.

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