In 1741 George III of England established the crown colony of New Hampshire, fixed its present-day boundaries and installed one Benning Wentworth at its head. Wentworth, as governor, was put in charge of Fort Dummer, then a remote outpost planted on the opposite (west) bank of the Connecticut River. Using this miniscule toehold, Wentworth proclaimed jurisdiction over the vast, largely unexplored “no man’s land” beyond the Connecticut recently gained in the historic ceding of French Canada to Britain. Actually, New York was first promised this territory. But Wentworth embarked upon an aggressive campaign, chartering townships from Massachusetts northward, thereby sowing an enduring legacy of land-grabbing and real estate controversies that would characterize the original settlement of Vermont, known then as the Hampshire Grants.
Within twenty years all the prime agricultural soils right up through the Champlain Valley were bought up by wholesale land developers (Ira and Ethan Allen, notably, among them) looking for a tidy return off a burgeoning colonial population. Remaining marginal farmland lay in hill country. Records show that on June 8, 1763, Wentworth issued a charter containing thirty-six square miles (23,040 acres) of virgin wilderness to a group of sixty-five investors, one of whom was named Benjamin Underhill. This land went for exactly one cent per acre. On this same day Westford, Stowe and the now extinct township of Mansfield were chartered in different syndicates comprising many of the same shareholders. Jericho had been born the day before. These original owners never intended personally to clear this frontier. They were land speculators. Most joined several standard sixty-five-member coalitions purchasing thirty-six square miles at a penny an acre. Likely none ever physically visited their holdings any more than a contemporary market trader would bother inspecting some corporate plant. In this New World exploitable wilderness was everywhere just over the perceived horizon. It was a brisk commodity—parcelled up, shuffled about and horse-traded off to young, hardy, gullible frontiers people desperate for a new beginning someplace.
In the following year of 1764 the Hampshire Grants, now a gridwork of 131 separate townships, were mostly all sold off, though few settlers had actually arrived. But by year’s end, following decades of dispute, King George himself finally ruled that this whole (literal) shooting match west of the Connecticut River had all along belonged to New York, not New Hampshire. Benning Wentworth’s scheme swiftly unravelled and he eventually resigned under scandal. New York began selling its own charters directly adverse to the so-called “Wentworthless” claims. In fact, in 1776 New York sold a tract of land to one Frederick Rhinelander of New York City, which included parts of Milton, Westford and Underhill. But in the tempestuous months preceding the outbreak of revolution, entrenched Hampshire Grantees in first-settled areas like Guilford and Bennington (named after you-know-who) fended off arriving homesteaders armed under New York authority. In fact, the Green Mountain Boys of Revolutionary legend originally banded to fight not British soldiers, but Yorkers—fellow settlers.
Thus, for pioneers contemplating “going into the Grants” during the 1760s and 1770s migration north offered the terrifying prospect of colonizing territory ravaged by dispute and revolution. A breed apart, those lost souls who dared stepping into this wilderness faced a pantheon of nemeses: native Abenaki, French trappers, British soldiers, New York militia, Green Mountain vigilantes, not to mention starvation, wild animals and brutal cold.  Needless to say, Benjamin Underhill and his peers never saw much quick profit. It would take decades more for this hill country to start populating.
On September 12, 1785, a group of landed gentry gathered at the home of one Abraham Underhill (presumably a relative of Benjamin) in Dorset, Vermont. This was the first formal meeting of these sixty-five original shareholders—or their survivors—who twenty-two years earlier had speculated, sight unseen, on a chunk of uninhabited wilderness lying somewhere nine days’ walk north of them. Much had transpired over those intervening years. New York, Massachusetts and New Hampshire were now constituents in the new, thirteen-member federation.
Although the Green Mountain Boys had valiantly supported the War of Independence, the Continental Congress snubbed their membership mainly out of deference to the powerful New York delegation still smarting from rivalry and the loss of substantial charter fees to Wentworth. But residents of the Grants stood defiant, proclaimed themselves a sovereign nation, drafted their own Declaration of Independence and Constitution, and even minted their own currency. Eventually they adopted the name: Vermont. Finally, in 1785 they laid to rest the quarter-century of antagonism by paying off New York and legitimizing Wentworth’s originally bogus charters. In that year the ruggedly self-reliant Republic of Vermont was finally poised for prosperity—and for inevitable admission, six years later, into the Union as the fourteenth State.
There was certainly some urgency to the 1785 shareholders meeting at Mr. Underhill’s home in Dorset. Now that the great feud was finally over, a land rush was on and civilization was swiftly pushing back the frontier. Pioneers had already settled on the Browns and Lamoille River flatlands. So a committee of three was appointed to dispatch a surveyor posthaste. “Surveying” the Vermont wilderness in 1785 entailed nothing of today’s professionalism. It was a combination of bush-whacking, dead reckoning, eye-balling and much bare-fisted negotiation with sundry squatters, neighbors and adverse claimants in a conspicuous grab for the best cropland. By the time this surveying team arrived, the choicest alluvial pickings had already been staked by surrounding townships.