John Winthrop the Younger

Francis Lovelace languished in the Tower of London in 1675, unaware he had created the Boston Post Road two years earlier and forever shaped New England.

He had been the royal governor of New York, and he had sent the first official post rider to Boston. Sometime in February 1673, the first mail ever arrived in Boston from New York City via the Boston Post Road. (Some put the date at Feb. 6, some at Feb. 11. All dates Old Style.)

The first post rider started out sworn to obey Lovelace’s instructions to behave civilly, to ask the governor of Connecticut how to form the best post road and to mark the trees for the direction of passengers.

Thus Francis Lovelace initiated both the U.S. Postal Service and the Boston Post Road.

All Boston Post Roads Lead to New Haven

There are actually three Boston Post Roads, all of which merge in New Haven.

The Upper Road, or the Old Boston Post Road, runs from Boston through Worcester, Springfield and Hartford.

The Lower Road heads south from Boston through Dedham and Providence, then runs along the coast of the Long Island Sound.

The Middle Road, less used than the others, leaves Boston through Dedham, Medway, Uxbridge, Douglas, Pomfret and Coventry to Hartford, then to New Haven through Wethersfield, Berlin, Meriden, Wallingford and North Haven.

Much of the Post Road is now U.S. Routes 1, 5, and Route 20.

King Charles II

Though Francis Lovelace set out the guidelines for what would become the Boston Post Road, King Charles II had the idea first.

Charles had decided to seize the tiny colony of New Netherland and give it to his brother, the Duke of York. He sent four warships to the settlement and demanded the Dutch surrender. They did. Charles appointed Francis Lovelace, brother of the poet Robert Lovelace. as royal governor. He wanted to knit his English colonies together more closely – especially since the Dutch just might try to recapture New York.

Charles wrote to Lovelace in 1672. “His Sacred Majestie” had “injoined his American subjects to enter into a close correspondency with each other.”

On Dec. 27, 1672, Lovelace wrote to Connecticut Gov. John Winthrop the Younger, presenting him with two “rarities:” a “pacquet of the latest intelligence I could meet withal, and a post.”

He wrote that he thought Charles’ idea “as the most compendious means to beget a mutual understanding.”

Winthrop was the perfect person to help carry out such a plan. He had traveled the post road himself.

Winthrop’s Journey

In the earliest days of the New England colonies, towns were surrounded by wilderness. The only roads emanated from the meetinghouse. To the extent the towns were connected, they were connected by Indian trails – a foot-and-a-half wide in some places, across surging rivers in others.

In 1635, someone had actually journeyed to Connecticut from Boston and returned safely.  The Puritan leader, John Winthrop, found that remarkable.

Ten years later his son, 39-year-old John Winthrop the Younger, loaded his horse and set out from Boston on foot along what was then called ‘The Bay Path’ (later the Upper Boston Post Road). He intended to find a spot to start an ironworks along the Connecticut coast.

Howling Winds

Winthrop traveled through howling winds, heavy snow, driving rain and freezing temperatures. He slept on the ground, filling a net with grass for a blanket. He got lost several times, fell into a stream once and cut down a tree to cross another.

In Hartford, Winthrop stayed in an actual tavern, which the leaders of Connecticut had asked Thomas Ford to run because of “want of entertainment.”

He passed through Saybrook in bad weather and waited six days to cross the mouth of the Connecticut River before arriving at his destination – New London. He found a spot that suited him for his ironworks and returned along the coast of the Long Island Sound to Providence – then known as the Pequot Path, later the Lower Boston Post Road. In Providence he stayed with Benedict Arnold, the traitor’s great-grandfather. Several days later, exhausted, he reached Boston. The trip took 26 days. “Deo gratias,” he wrote at the end of his travel diary, or “Thank God.”

John Winthrop the Younger then moved his family to Connecticut and became the state’s longest serving governor.

Mr. Post Rider

After about 1650, the colonists began to travel more frequently between towns. There were few horses in the first decades of the 17^th century. As the equine population grew, New Englanders could ride longer distances. And as trade with the West Indies flourished, they drove their livestock from the interior to market on the coast.

In 1672, Winthrop received the letter from Lovelace seeking his cooperation in setting up the mail service. He would have received the letter from a Native American, a shipmaster, a servant, a traveler or maybe a cattle driver.

Lovelace proposed recruiting a post rider, “a stout fellow, active and indefatigable, and sworne as to his fidelity.” He was to “cause to be apprehended all fugitive soldiers and servants.”

On the first Monday of every month, the post rider was to leave New York and return from Boston within the month. Hartford was to be the first relay station for him to change his horse.

The mail was to be in different “baggs,” one for each town to which the mail would be delivered.

Lovelace suggested that Winthrop talk to “some of the most able woodmen,” to find the easiest way, which eventually would become the Boston Post Road.

First Mail

Lovelace intended the first mail to leave New York on Jan. 1, 1673. Lovelace waited, though, because he wanted to send Winthrop the latest rumors about a convoy of Dutch warships. The post rider left on Jan. 22, 1672/3.

The Memorial History of New York describes the reaction to that first post rider, Mathias Nicolls.

It is recorded as creating great excitement in the little village of Harlem, when that first postman drew up at the tavern door to refresh himself, as he undoubtedly did, with some good home-brewed Harlem beer — his ‘port mantles’ (portmanteaux) crammed with ‘letters and small portable goods,’ the ‘locked box’ in the office of the colonial secretary accumulating the next month’s mail, and what he had brought, being carried to the ‘coffee house’ to be ‘well thumbed’ until called for.’

Nicolls continued his monthly journey. In July of that year, Lovelace rode from New York to Hartford to discuss the postal service with Winthrop.

They agreed, for example, the post rider should direct travelers, who could accompany him, to the best roads and inns.

But while Gov. Lovelace was meeting with Gov. Winthrop in Hartford, a Dutch naval squadron appeared in New York Harbor. The city surrendered and the Netherlands won back Niew Amsterdam.

Lovelace returned to England in disgrace. The Duke of York blamed Lovelace for the loss of the colony named after him. Lovelace owed him 7000 pounds, and York confiscated his estates. Committed to the Tower, Lovelace contracted dropsy. Authorities released him in April 1675. Francis Lovelace died broke on Dec. 22, 1675.

Postscript

The Dutch gave up New York in a little more than a year, but King Philip’s War broke out and temporarily ended the postal service.

The challenges of riding from Boston to New York along the Boston Post Road were vividly described in the journal of Sarah Kemble Knight.

With thanks to The King’s Best Highway: The Lost History of the Boston Post Road, the Route That Made America by Eric Jaffe and The Old Post Road by Stewart H. Holbrook. This story updated in 2023.