The Edgartown-Vineyard Haven Road dates back to the late 18th century and probably earlier, although not entirely in its modern location.
It was along this road that British troops drove thousands of plundered sheep and other livestock during the infamous Grey’s Raid of 1778. Scouring the Island for sheep, cattle, weapons, food, and valuables, troops under the command of Lt. Colonel Sterling marched from Holmes Hole to Edgartown and returned with livestock and loot along this wooded road, which they loaded onto transport ships in Holmes Hole Harbor and departed, leaving the Vineyard destitute.
As you were traveling from Edgartown, the old, meandering road came to a fork not far from modern County Road in Oak Bluffs (near Quantapog Road). The right fork — what we know today as County Road — took you along the edges of farmers’ fields and sheep pastures to the east side of the harbor to Eastville. The left fork sank into the uncut forest, eventually bringing you to the west side of the harbor to Holmes Hole.
At the fork was a cluster of ancient farmhouses and the Farm Neck School. The oldest English settlement in what’s now Oak Bluffs, this neighborhood dates back to the commercial 17th-century tannery and dam of Nicholas Norton at Majors Cove. His son Joseph Norton’s house was later moved to Edgartown, where it still stands as one of the oldest surviving houses on the Island.
The Farm Neck Schoolhouse was built in 1775 or 1761 (reports vary), evidently rebuilt about 1830, and remained in operation through the late 1800s. The building itself survived into the early 1900s. (Its modern location would be on County Road just north of Quantapog.)
One of the earliest teachers here was William Butler (1761-1844) whose diary is kept at the Martha’s Vineyard Museum. He also owned what would become the Camp Meeting grounds at Oak Bluffs. In a typical 1792 entry in his journal, Butler wrote:
“Wednesday Jan. 11. Very cold – A singular instance took place this day in school as the scholars stood up spelling, James Johnson struck Jethro Coffin over the head with his hand, being vext with him for pulling hair he said, as he was hanging up his slait. I think it was not owing to my not keeping order in school but to the ungarded disposition of the boy.”
One of the later teachers here may have been Ms. Martha W. Luce, a schoolteacher who lived nearby in 1860.
Before Cottage City put our Island on the map, “Farm Neck” was the general name used for virtually all of what we now call “Oak Bluffs” — everything west of Sengekontacket and east of the Lagoon, from Eastville to the area comprising downtown Oak Bluffs. Except for the tenuous barrier beaches on the east and west both known as “Beach Road,” Oak Bluffs is indeed a neck of land, a peninsula. Eventually, the name “Farm Neck” began to refer only to the land west of Majors Cove. The principal access point to all of modern Oak Bluffs, the fork in the two County Roads was a natural crossroads for a settlement.
Here, in the mid-1800s, was the small farm of the Wilbur family. Adjacent to the fork on the south, the Wilburs raised rye, corn, oats, and peas on their small, 34-acre farm, from which it was said you can see the church steeples of Edgartown across the clearcut fields along Sengekontacket. Across the road from the Wilburs was the much larger farm of Elijah Norton (1795-1881), who maintained a flock of 60 sheep on his 225 acres. Just east of them lived the Kidder brothers — James and Charles, who each kept a sizable farm near Majors Cove. Nearly 200 acres combined, here the brothers grew rye, corn, oats, potatoes, and barley, raised sheep, and produced butter and wool. (As a young man, Stephen had been one of the survivors of the infamous 1824 mutiny on the whaling ship Globe.) To the north, Elijah Norton (1795-1881) maintained a sprawling 225-acre farm, with sheep and cattle, and fields of rye, corn, oats, and potatoes. Norton was one of the largest wool producers in town.
In 1851, the towns of Tisbury and Edgartown (which at that time still included Oak Bluffs) ponied up $2,850 ($1,950 from Edgartown and $900 from Tisbury) to lay out a new, straighter highway between their towns — the one we know and love as the Edgartown-Vineyard Haven Road. The old Holmes Hole Road was relegated to use as a byway. Today, a large section of the old road has become a defining path in the Land Bank’s Southern Woodlands Reservation trail system.