Anchoring one end of Eastport’s main street downtown is the Post Office and former Customs House.
Though the Customs role has moved closer to the Breakwater but not so the mail, especially this time of year..




You never know what we'll churn up in cleaning a stall
Anchoring one end of Eastport’s main street downtown is the Post Office and former Customs House.
Though the Customs role has moved closer to the Breakwater but not so the mail, especially this time of year..




Maine is larger than the rest of New England combined, and except for much of Vermont, it was settled much later than the rest of the six-state region. That is, the parts of the state that were ever settled at all. Half of the Pine Tree State has no year-round population at all, for good reason.
The result is that there are paved roads where you can drive for miles and see nary a utility line or a mailbox, much less a house. Often, the only human activity you detect is timbering or mining. Hunting and fishing are a way of life. It wasn’t that far out of Bangor I used to see the bear-hunt guide sign.
Those roads remind me of driving from town and out toward a mountain pass on my way to trails in the high country out West.

Downeast Maine’s open blueberry barrens on the ridges, meanwhile, give me a sensation of the Big Sky Country of Montana or the Horse Heaven Hills of Washington state, except that the blue overhead isn’t the same deep intensity.
I believe that the presence of Indigenous peoples is another part of the mix. Eastport is adjacent to the Passamaquoddy’s Pleasant Point Reservation, as we’re reminded every time we drive to or from our island. They’re one of the four tribes comprising the Wabanaki Alliance in the state.
Yes, there is a kind of frontier feel around here. I’d suggest calling the area the Far East, but that name’s already been taken.
Fact is, many of the old ships that sailed to the Far East were built along these shores rather than those of the Far West.
Speaking of juicy.
Sandwiched in between the arrival of Pilgrims at Plymouth and the Puritans at the Massachusetts Bay colony, we have the libertine plantation at Mare Mount, or Merrymount, on Boston’s South Shore. It’s a provocative whiff of how New England life could have turned, had Thomas Morton successfully warded off the rival raiders.
The very name “merry” at the time was often a synonym for sexual trysting. As for Merry-Mount? It couldn’t have been more graphic.
Unlike Plymouth, this settlement was prospering and welcoming misfits.
Think of hippie. Maybe even commune. Dancing naked with Natives around a giant maypole, one that’s flagrantly phallic. Not just pagan but also reflecting some lingering Devonshire traditions taken to an extreme. (Significantly, for comparison, most of early Dover’s settlers came from Devon, not the East Anglia of Puritan culture.)

That’s the short version, though there’s much more sketched out in my upcoming book.
And after Merrymount comes crashing down, its founder finds shelter in Sir Ferdinando Gorge’s Maine, not far from Dover.
No, early New England wasn’t all stern Puritans, not by a long shot, no matter how much they tried to keep a lid on.
Nearly two decades later, facing the Quaker outbreak, did Puritan authorities fear the Friends movement might trigger another Merrymount in their midst? As I’ll show, Quakers were anything but quaint and respectable when they show up, though I can assure you they stayed sober rather than make merry. Ahem.
But they were still an alternative to the Puritan rigidity.
When Edward Hilton settles on Dover Point, his brother William is dwelling in the Plymouth Bay colony. It’s one more suggestion, in fact, that Edward knew about the Piscataqua watershed before setting forth himself.
William arrives on the second ship to the Pilgrim plantation, followed by his wife and family on the next. They definitely aren’t Pilgrims (the term wasn’t even in use then – Separatists was more accurate). And, for that matter, despite sharing a basic Calvinist theology, the Separatists hold some sharp differences from the Puritans who show up later.
Critically, roughly half of the settlers at new Plymouth aren’t members of the Separatist faith. And that includes the only ordained minister in the colony.
Thus, when William and his wife arrange for a secret Anglican (that is, Episcopal) baptism for their infant, a scandal erupts that sends them scurrying northward and brings to light the sordid background of the now disgraced minister who is promptly banished. (No spoiler here – but you’ll still have to read the book.) These events do present a grittier alternative to the Thanksgiving scenario we usually trot out about the Pilgrim experience.

William winds up in New Hampshire, settling at the Pannaway plantation at the mouth of the Piscataqua River, where he’s soon making salt to be used for preserving fish for shipment.
And then, in the demise of Pannaway, he’s finally at Dover Point.
This isn’t the way his arrival in Dover is commonly painted. Quite simply, he isn’t one of the first two settlers. Thomas Roberts, Edward’s apprentice, earns that honor.
Still, like his brother, William is both a member of the powerful fishmonger guild in London and literate. And things get a bit rowdy when he moves on from Dover to live on the Maine side of the river.
Yeah, if you’re looking for gossip, there’s some juicy stuff on his part, especially when we meet his last wife. She’s definitely not holier-than-thou.
It’s hard for modern Americans to understand a basic reality of European colonies in the New World.
None of the players in the story own the land they’re dealing with.
Not the settlers, even though they’re clearing it and building on it.
Nor the proprietors or investors, either. They’re more like developers who offer leasing opportunities. Think of rental agents.
Nor the Indigenous tribes, surprisingly, even though many of the settlers also negotiate a payment to them for their land. The use of their land, more accurately. Admittedly, the payments are largely symbolic – a bushel of corn a year, for example.
No, quite simply, all land “belongs” to the king, and he allocates the privilege of using it as a means of leveraging his own prestige and power.
Under the feudal system, that would mean grants to barons and other lords in return for their fealty.
They, in turn, could dole some out to knights, who then become wealthy, as well.
Add to that the gentlemen farmers, living off the rents to their estates.
And then yeomen, who are still free on their own tenants, as their small holdings were called.
And husbandmen.
And, somewhere below that, the serfs who are bound to the land and its holder. Well, by this point in time, they’d been freed but were still at the bottom of the ladder.

~*~
THIS IS THE MODEL OF LANDHOLDING – not landownership – up through the American Revolution.
Its assumptions are quite different from those of modern Americans. What do you mean? I don’t own the ground under my house and barn?
No, you don’t. And you still have to pay rent on it.
~*~
AS A FURTHER COMPLICATION, charters could be revoked or rewritten.
Falling out of the king’s favor would have costly and dire consequences.
As my upcoming book describes, this land arrangement affected Dover and the rest of New England through a series of realignments and controversies and attempted evictions.
In fact, it almost leads to a rebellion in Boston Harbor against the king a century-and-a-half before Paul Revere’s midnight ride. Well, that’s one aside I don’t develop. There’s too much else going on along the Piscataqua.

Eastport’s Civil War veterans had good reason for naming their Grand Army of the Republic post after Major General George G. Meade. Not only had he commanded the successful Union troops at the Battle of Gettysburg, he was stationed in Eastport after war to curb the Fenian Rebellion, an Irish liberation attempt that had organized in the United States and conducted raids in neighboring Canada.
During his time in Eastport, he caught pneumonia and nearly died, and some residents got to know him first-hand. One – the wife of the owner of the house where he was staying – complained bitterly for years afterward about his poor aim in spitting tobacco juice all over her home. Let’s hope he was better with a firearm.
The local post wasn’t the only one named in his honor, by the way, and the organization itself became a powerful force within the Republican Party, helping to elect at least four its members to the White House and pressing for progressive legislation.
In 1881, the local post took over a two-story frame structure at 6 Green Street as its meeting hall. As its membership – limited to Union veterans of the Civil War – died off, the building passed to the local Veterans of Foreign Wars for its post. The building next door included a bowling alley, roller skating rink, and dance hall all fondly recalled by youths of the time.

The murals and ceiling were long hidden by a dropped ceiling and rediscovered only shortly before 2014, when the building was gifted to the Tides Institute and Museum of Art.

Tony Castro of New Gloucester, Maine, has been renovating the murals. Despite severe water damage, they may be the only surviving interior of their kind in the state.

The Tides Institute has also been gifted with important Civil War artifacts and documents, which may be displayed as the museum adds gallery space.

From the git-go, there’s been a rivalry between Portsmouth and Dover, though a closer look reveals it’s more nuanced than what we usually think.
The 1622 contract for developing the Piscataqua watershed allows for more than one vessel to arrive and more than one settlement to be planted along the river.
Scotsman David Thomson is the head of the operation. He sets forth in the Jonathan and establishes his fortified Pannaway plantation at the mouth of the river in today’s Rye – not Portsmouth, contrary to the Port City’s claims of founding. He’s highly placed politically, somehow having the ear of King James I. And specifically, he’s the only one named in the grant.
Pannaway faces the open Atlantic, with salt marsh to its back.

~*~
IN CONTRAST, when the Providence arrives a month later, she apparently sails straight up the river to today’s Hilton Point aka Dover Point, where Edward Hilton and Thomas Roberts then set up operations. They disembark at Pomeroy Cove, which they name for Leonard Pomeroy, one of the three principal backers of the project. He’s also Lord Mayor of Plymouth, England, home of the company, and co-owner of the ship that’s brought them this far.
As I detail in my upcoming book, Hilton likely knew of the site even before setting sail. It was far enough inland to be sheltered from violent storms. Vast forests extended from the riverbanks, with timber for shipbuilding, piers, and barrels as well as homes and bridges and wild game for the taking. Best of all, the point was a confluence of rich tidal waters, with the Great Bay estuary on one side along with its tributary streams and, on the other side, the Piscataqua and its Cochecho and Salmon Falls rivers. Cod, salmon, sturgeon, eels, herring, oysters, clams, and lobsters are bountiful. Why go out to sea when the fish come right up to you?
While Pannaway is thoroughly documented, in part through its stream of visitors, its existence is short-lived, and the site’s abandoned by 1626, when Thomson relocates to an island in Boston Harbor and disappears soon after. His widow then promptly marries Samuel Maverick – yes, the source of that word. It’s a rough-and-tumble world.
~*~
OUT OF THE SPOTLIGHT of documentation, Hilton and Roberts continue on, in time joined by Edward’s brother William and their sister or possibly cousin Rebecca along with more family.
Either way, Roberts and Rebecca soon marry and start a farm about a mile from the point – they later move it another mile-and-half – but theirs will still be the oldest family-owned farm in the future United States well into the 20th century.

It must have been lonely through much of that first decade. The Hilton-Roberts clan was definitely on the frontier, and ongoing war in Europe cut off much ship traffic.

Edward Hilton is, however, definitively rewarded for his six years of habitation and hard labor by a charter giving him clear control at Dover Point. And they must be prospering, as seen in assessments placed on their province or his brief return to England for the legal document, perhaps a fish delivery, and definitely a marriage.
While Thomas and Rebecca Roberts remain in Dover for the rest of their lives, her brothers eventually move on – Edward to Exeter and William, by degrees along the Maine side of the Piscataqua. All of their lives take colorful turns along the way, which I relate in the book.
Even though Portsmouth baldly claims 1623 as its founding date, it had no European settlement until the Laconia Company chose to set up operations there in 1629 or 1630, calling their site Strawbery Banke. Yes, that was one more convolution of investors.
~*~
AND THAT’S THE BARE-BONES VERSION. There’s plenty in my upcoming book to flesh it out, some of it rather earthy – especially when we get to the contemporaneous and scandalous Merrymount plantation down on Plymouth Bay.
Fact: New Hampshire is the second-oldest state to be settled in New England. Older than Connecticut, Rhode Island, Maine, or Vermont.
To understand why a third of Dover became Quaker in the mid-1600s, we need to go back to the very founding of the colony.

The common presentation of history has New England settlement being prompted by a quest for religious liberty – you know, the Pilgrims and then the Puritans – but close examination finds that’s not the full story.
For instance, the first permanent English habitation, Plymouth in southern Massachusetts, is only half Pilgrims – the other half is diverse individuals looking for economic opportunity. The colony is also heavily in debt to investors in London who dictate much of its operation. Religion isn’t on their radar.
There’s nothing altruistic in the investors’ role. They’re looking for quick returns on their money. Their eye is on gold and silver or at least a shortcut to the Far East and its lucrative spices. Trade for furs could also be lewdly profitable. And then there’s the possibility of creating landed estates in the New World, where they could live at ease as gentlemen farmers supported by the rents paid by their tenants once the time’s ripe.
All of that puts the investors at odds with settlers who are out to establish homes, livelihoods, and security.
~*~
AS A FURTHER COMPLICATION, the investors come in layers. One company holds rights to the development of all of New England and then enters agreements with others interested in specific tracts, sometimes within a specified timeframe.
Sir Ferdinando Gorges is the godfather of all this and plays a crucial role in the birth of Maine, which emerged largely on its border with Dover. Quite simply, the Maine side of the Piscataqua River is a big part of early Dover’s community.
Sir Ferdinando’s business associate, Captain John Mason, emerges more directly as the proprietor of New Hampshire itself.
Together, only two years after the Pilgrim venture, they negotiate with a band of Devonshire merchants to settle on the Piscataqua River, today’s border between New Hampshire and Maine.
~*~
THEIR AGREEMENT SPECIFIES seven settlers – and, as we will see, that implies their families, servants, and laborers – intent on commercial opportunity. Forget religion.

The Puritans, pointedly, are nowhere to be found. They’re still seven or eight years off in the future. Their arrival to the south of New Hampshire will, however, spark a culture clash and ongoing power struggle that will include Maine. As you’ll see, the plot thickens.
In the meantime, the odds are greatly against the survival of the Piscataqua enterprise.
Other attempts in New England have failed, some without a trace, as would others. The Plymouth colony is faltering.
Remember, nobody finds gold or silver or that shortcut to China.
Even so, Gorges and Mason leave a deep imprint on the future Dover.
As do Edward Hilton, a member of the powerful fishmongers’ guild in London, and his apprentice, Thomas Roberts. Their outpost at Dover Point is the start of the seventh oldest permanent European settlement in the United States – and the third oldest in New England.
Edward has been recognized as the Father of New Hampshire.
Thomas, however, is generally neglected, even though he has a more central role in its continuing development. He even becomes Quaker, for all intents and purposes. And though an apprentice, he’s not a disadvantaged youth looking for a step upward. He comes from a privileged family, and his father, by some accounts, is about to become a baron.
~*~
ALL OF THAT’S PART of what we’ll be celebrating next year – 400 years after their arrival. And my new big book tackles some of the story.
In my book The Secret Side of Jaya, her sojourn in the Ozarks introduces her to a magical vale in the woods just beyond their house. It’s also the site of a water-powered grist mill she begins to frequent in her free time.
Here are ten facts about the historic industry.
Among the artists-in-residence the Tides Institute invited to town last year was tintype photographer John DiMartino from Brooklyn.
He was certainly the most visible, with his big camera and tripod everywhere and his workaholic hours. He was enthralled with the place, its light, and its people.

Curiously, his medium gave everything he shot a back-in-history quality, as well as reversing the subject before him.
Here’s what he did to me.


For more of his portfolios and other characters he captured in town, check out his website, johndimartinojr.com.