By the beginning of the 18th century, the dwindling peninsula Indian tribes had been herded, through a series of wars and peace treaties, into several settlements, some of which were officially recognized and reserved for them by the colonial governments, and some of which were simply located on unclaimed land. One of the latter was the last refuge of a band of Indians – probably Assateagues – who had been forced to move several times, leaving the Buckingham area in eastern Somerset (now Worcester, near Berlin) at an unknown date, and migrating north in search of a new home. They settled at a place called Assawamen, which was probably a tributary of the Sound known as Indian Town Branch (now Dirickson Creek), but moved north again to the south side of Indian River, which was the de facto boundary between Maryland and Pennsylvania at the time. The subject of this article, their final recognized settlement, was in existence by 1705, and was known by several similar names, including Askeksy, Askekesky, Askeckeky, Askekson, Acksquessance, and Askquessence. The Indians themselves, because they had settled near the Indian River (also known as the Baltimore River) , became known as the Indian River Indians. It should be noted that this name referred to this specific band of Indians, although others lived on both sides of the river. Their name for themselves does not appear in any records from the period.
The so-called Indian River Indians first appear in official records dated May 1705, when their chief Robin appeared in Annapolis and signed a peace treaty on behalf of “Queen Wyransconmickonous.” Representatives of the Nanticokes and Choptanks also signed the treaty. Robin went on to tell Governor John Seymour that his people had “Extremly Suffered of Late Years by being disturbed & Expulsed from their several Settlements in Towns,” and were living in a town at the head of Indian River, but were “Continually Threaten’d to be Driven from thence…” He requested that the land on which their settlement was located, as well as one thousand adjacent acres, be reserved for the tribe’s use. The request was approved.
In modern terms, Askeksy was located south of Millsboro between Irons Branch and Route 24. The branch was known as Indian Town Branch or Indian Branch during the 18th century, and clearly matches the southern boundary of the tract. This boundary more or less survives as Indian Town Road (which was known as Injun Town Road for decades and as recently as a few years ago) and a portion of Hickory Hill Road. The location of the northwestern boundary is a bit less clear, but it seems like Route 24 follows it roughly, or was at least laid out in relation to portions of it. The following map shows how modern roads roughly outline the old reservation over three hundred years after it was established.
Based on descriptions of nearby tracts surveyed for William Burton, as well as modern estimates of the extent of the Pocomoke or Cypress Swamp prior to drainage and timbering efforts, the reservation was probably somewhat swampy, or at least very close to the swamp’s northern edge. The description of a tract named Panter Swamp mentioned a waterhole on or near the west prong of Indian Town Branch. There were still black bears and timber rattlesnakes in the area at the time.
At about the same time that Askeksy was established, most of the Nanticokes moved from their reservation known as Chicacoan Town, near Vienna, to a site on Broad Creek which came to be known as Broad Creek Town. Aside from the fact that their leaders and Robin appeared in Annapolis at the same time, there is little information about their dealings with their new neighbors, just fourteen miles away. Recently I wrote about a so-called horse road which was in existence in 1748, connecting Broad Creek and the head of Indian River; this road may have begun as a trail between the two Indian settlements.
Though the Indian River Indians aren’t mentioned in official records nearly as often as the Nanticokes, if the Nanticokes’ experiences during this period are any indication, they struggled to preserve their property and way of life as more and more land was cleared and farmed by the English. Sometimes the white farmers interfered with Indian hunters. Perhaps that’s why they joined the Nanticokes, Choptanks, Pocomokes, and visiting Shawnees at a place called Winnasoccum or Wimbesoccom for a secret powwow in June 1742. The tribes planned to massacre the local English settlers and retake the peninsula with the help of the French, who supposedly promised to land on the coast. The plot was discovered and thwarted, several Indians were arrested and interrogated, and in August the leaders of the Nanticokes, Choptanks, Indian River Indians, Pocomokes, and Assateagues signed a new, highly restrictive peace treaty. Tom Hill and Robin (probably the first Robin’s son) were identified as chiefs of the Indian River Indians.
In the years following the suppression of the Winnasoccum Uprising, as the event has been labeled by some, many of the peninsula Indian tribes abandoned their lands and migrated to Pennsylvania. The Indian River Indians had already sold hundreds of acres to local English settlers prior to 1742, and sold the remainder of their reservation to William Burton in 1743. There is no known record of their existence as an organized tribe or band following this sale, and strictly speaking, their fate is unknown. They may have joined the Nanticokes at Broad Creek Town, many of whom moved north in 1744. Perhaps they moved north, too, or perhaps, like some of the Nanticokes, they lingered in the area, intermarrying with whites and/or blacks and producing new generations of mulattoes who gradually adopted English ways and preserved vague traditions about Indian ancestry. If so, it seems likely that some would have joined the multiracial community on the north shore of the Indian River which was in existence as early as the 1840s, and which eventually spawned the Nanticoke Indian Association.
– Chris Slavens