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Early Settlements

Text by Lang Smith

Big Tree, Islesboro, ca. 1920
Big Tree, Islesboro, ca. 1920
Islesboro Historical Society

Islesboro was first settled in 1764 by Shubael Williams who built a log house next to Bounty Cove near the center of the island. It was originally called “Little Island,” then “Longue Island Plantation” and then “Long Island.” In 1789, this island and the adjacent islands including Seven Hundred Acre, Job’s and Lime were incorporated into one Massachusetts town called Islesborough, Maine being part of Massachusetts until 1820.

Fourteen miles in length and up to three miles in width, Islesboro is today part of Waldo County on the midcoast of Maine dividing East and West Penobscot Bays. Early settlers arrived by various seacraft (or by sleigh over frozen water) bringing with them all that was necessary to survive. They found a land totalling 6,000 acres, mostly wooded with little good timber, barren ledges and swamps. Only one third of the land was good for farming, but the fishing was excellent.

Travel was difficult at all times but especially in winter on roads built and maintained by each landowner who built permanent gates across their part of the road to keep farm animals from wandering. Very few residents could afford horses so walking was the primary means of transportation. For those who did not go to sea for a living, time was spent clearing, farming and tending to the cattle, hogs, sheep, goats and chickens. Accordingly, most stayed close to home in small settlements. Visiting from one end of the island to the other was virtually unheard of. It was not until the advent of three summer colonies that the horse and buggy became popular. The automobile was banned from the island until 1933.

Turtle Head, Islesboro, ca. 1915
Turtle Head, Islesboro, ca. 1915
Islesboro Historical Society
Meadow Pond, Islesboro, ca. 1900
Meadow Pond, Islesboro, ca. 1900
Islesboro Historical Society

TURTLE HEAD AND MEADOW POND
According to an early history of Belfast, Turtle Head at the north end of Islesboro was named by Thomas Pownall (1722-1805), the English Governor of Massachusetts. The Meadow Pond settlement offered its residents great views and easily obtainable fresh water. In winter, it was the single source of ice which was floated downstream to Sprague’s Cove and then shipped to far off lands. Area children were served by one school in the Sprague District.

Lime Kiln Wharf, Islesboro, ca. 1900
Lime Kiln Wharf, Islesboro, ca. 1900
Islesboro Historical Society

PRIPET
This settlement on the northeast side of Islesboro, extending from the Bluff Road to Turtle Head, had several small stores and a post office. Its young residents attended the Parker School. Although road signs to Pripet still exist, no one knows the actual boundaries or how it got it’s name. Reference to this name cite the Pripet River and Pripet Marshes in the Ukraine. These usually frozen marshes were probably similar to those found at Parker Cove and Coombs Cove.

THE BLUFF
Further south on one of the two highest points of land on Islesboro was The Bluff, a settlement of only seven houses. In 1884, a school house was situated near the Bluff because the local students had to travel too far to attend the Parker School in Pripet. George W.C. Drexel, a banker from Philadelphia, acquired most of the Bluff in the late 1890s. From his highly prominent location, he could view his 300-foot square-rigged yacht “Alcedo” swaying at anchor moored in the deeper waters of the East Bay. This same ship, donated to the U.S.Navy, was converted to a warship and was the first vessel sunk in the war by German submarines in 1917.

Ryder's Cove Wharf, Islesboro, c. 1911
Ryder's Cove Wharf, Islesboro, c. 1911
Islesboro Historical Society

SABBATHDAY HARBOR/RYDER’S COVE
This harbor was named by the fishermen who, after weeklong labors, rested in its sheltered waters on Sundays. The southern portion of Sabbathday Harbor was called Saturday Cove. Since the original settlers found the acres surrounding the harbor unsuitable for farming, it was available for purchase by the first seasonal visitors from the Bangor area. Benjamin Ryder (1818-1881) who had inherited land on the western side of the harbor, built a small boarding house next to the steamboat wharf in the early 1860s. This was the Islesboro’s second wharf following the commercial wharf built next to the lime kiln in Pripet. By 1868, a three story addition was attached to Mr. Ryder’s boarding house to accomodate the increasing demand. Sabbathday Harbor was now also called Ryder’s Cove. Although the hotel was reduced in size following the 1929 Depression and finally razed in 1950, most of the houses that were built by the visitors to the hotel are still standing. Ryder’s Cove remains a very popular summer destination. The Ryder School House was opened in 1864 to educate those who resided on the Main Road between North Islesboro and Pripet.

Guinea, Islesboro, c. 1910
Guinea, Islesboro, c. 1910
Islesboro Historical Society

GUINEA
Moving south past the Narrows, the sliver of land separating Bounty Cove to the east and Crow Cove to the west, one arrives in Guinea, home of the Pendleton School and at one time the island’s major store, F.S. Pendleton & Company. Captain Fields Seeley Pendleton (1870-1923) lived across the street from the store. He became the most successful entrepreneur ever to hail from Islesboro. At one time he owned more wooden sailing vessels than anyone in the United States. There are several stories about how the settlement of Guinea obtained it’s name but the most consistent is that a visiting sailor who shopped and resided in this area was from New Guinea.

Barber Shop, Islesboro, ca. 1900
Barber Shop, Islesboro, ca. 1900
Islesboro Historical Society

HEWES POINT
Hewes Point was named for Paoli Hewes, who established a salt works on the point in 1792. Hewes Point developed into Islesboro's second summer resort area in the 1880s, but was a year 'round community as well. It's wharf was busy transporting passengers and cargo to the mid-section of the island. Hewes Point consisted of a steamboat wharf, two dozen small cottages, a lumber mill, a brickyard, and a coal, as well as several small stores.

Mill Creek, Islesboro, ca. 1900
Mill Creek, Islesboro, ca. 1900
Islesboro Historical Society

MILL CREEK
The small settlement of Mill Creek was located between Dark Harbor Village and Grindle Point where Islesboro’s only lighthouse was built in 1850. A schoolhouse, the Creek School, located near the creek overlooking Broad Cove, provided education for area students. There was also a small coal wharf, a store and a tidal-powered grist mill on the creek. Coal was a very necessary commodity for heating, once most of the good firewood had disappeared. Electricity was not introduced to Islesboro until the late 1920s.

Dark Harbor Village, 1906
Dark Harbor Village, 1906
Islesboro Historical Society

DARK HARBOR
In 1884, the southern-most settlement of Dark Harbor was the least populated. While occupying almost one-quarter of the island’s total acreage, there were only twenty-six houses shown on the 1884 map. Only six houses were south of the Dark Harbor pool. A mainland developer took advantage of this sparcity and from the mid-1880s to the early 1890s acquired 1,500 acres for the grand total of $60,000. According to a very early survey of Islesboro, most of this southern land had been claimed by members of the William Pendleton and Thomas Pendleton families. Cousins William and Thomas were both born in Westerly, Rhode Island and emigrated to Islesboro from Stonington, Connecticut. Little did they realize that the land they farmed would eventually become some of the most sought after acreage on the East Coast.

700 Acre Island, Islesboro, ca. 1905
700 Acre Island, Islesboro, ca. 1905
Islesboro Historical Society

SEVEN HUNDRED ACRE ISLAND
Preferring to get away from the madding crowd on Islesboro, some of the early settlers chose to build homesteads on 700 Acre Island. John Philbrook, for whom Phillbrook Cove is named, acquired 100 arces in 1774 for about $2.00 per acre. This island was in School District No. 1 and, in 1884, there were only twelve families served. The famous American illustrator Charles Dana Gibson and his family built an 18-room house on the island in 1904 after a successful stay at the Islesboro Inn in 1903. Islesboro’s first fully equipped boatyard was built on Acre Island in 1920 and is currently owned by a descendant of Mr. Gibson.