In partnership with the Maine Memory Network Maine Memory Network

Islesboro--An Island in Penobscot Bay

Historical Overview

by Olivia Boucher and Melissa L. Olson

Survey Chart, Islesboro, 1884
Survey Chart, Islesboro, 1884

Item Contributed by
Islesboro Historical Society

Islesboro, Maine has a long, fascinating history that goes back to the 17th century. In August 1692, English Captain Benjamin Church arrived in Penobscot Bay with a company of men and landed on what came to be known as 700 Acre Island, a small island near present-day Islesboro. There, he encountered French traders and Native Americans and promptly chased them off. His company then sailed to the larger island of Islesboro, encountered more French and natives who also fled by boat. After confiscating a large quantity of beaver and moose pelts, Church and his men sailed away, and the recorded history of Islesboro (called Longue Island at the time) remains silent for the next 72 years.

Islesboro is long and narrow, approximately fourteen miles long and varying between three miles at its widest point and a few yards at the Narrows, depending on the tide. The bedrock geology of Islesboro and surrounding islands is unlike that of any other rocks in Maine. The entire island is located on what is called the Turtle Head Fault, so named for the upper most region of the island. This fault runs along both sides of Islesboro and is responsible for the shape of the island, having squeezed the bedrock together over the millennia. The bedrock consists mostly of slate, quartzite, limestone and greenstone – materials that at a later date provided income for those who came to settle on the island.

Many smaller islands surround Islesboro: Hutchins and Little to the east; Warren, Spruce, 700 Acre, Minot, Middle, Job, Lime, Lasell, Ensign to the south; Ram and Seal to the west. The Precambrian rocks of 700 Acre, Lime and Lasell Islands are some of the oldest in Maine, dating back over 600 million years. Some of the surrounding islands are inhabited - 700 Acre was once the summer home of Charles Dana Gibson, creator of the Gibson Girl. It is now the home base for a local boat yard. Warren Island became a state park in 1959 and is the only State Park that is accessible solely by water.

When the first settlers arrived on Islesboro, they found mostly spruce and a scattering of beech, birch and maple trees. Fish and clams were plentiful, as well as wild duck. Wildlife included fox and mink. Deer arrived in the 1930s and are now abundant. Moose occasionally swim from the mainland. Beaver make their homes in several locations on the island, while otter are present but scarce. Rabbits and squirrels are common, with occasional muskrats. Pheasants and partridge were introduced as game in the 1950s, and still inhabit the island. The island is host to numerous species of birds, including nesting pairs of bald eagles. Seals are frequently spotted off shore in the summer, especially on a small island known, coincidently enough, as Seal Island.

Ice Cleat, Islesboro, ca. 1860
Ice Cleat, Islesboro, ca. 1860

Item Contributed by
Islesboro Historical Society

The water surrounding Islesboro makes for a more temperate climate than that of the mainland, usually several degrees cooler in the summer and several warmer in the winter. However, there have been many recordings of Penobscot Bay freezing over and islanders walking or driving over the ice for necessities. This happened frequently in the 19th century, but only four incidents were recorded in the 20th century.

The first people to arrive on the island were the Penobscot and Tarratine natives, who camped here in the summer to hunt and fish. Huge shell middens have been found along the shores where natives camped for hundreds of years. After their initial scare by Captain Church's men, natives returned to Islesboro from the mainland to pick berries, dig for clams, pick sweet grass for baskets and split ash for containers. This practice continued into the 1930s and ‘40s, until it gradually died out. Many artifacts were collected over the years and found their way into private collections as well as the Islesboro Historical Society.

In 1620, King James I of England granted lands to noblemen, knights and gentlemen, which comprised most of present-day New England. In 1635, these lands were surrendered to Massachusetts settlers, but not before dividing some of the land into parcels, or grants. One of these grants became known as the Waldo Patent, which comprised approximately 1000 acres. It included the whole of Knox County (except for Fox Island) and most of present-day Waldo County, in which Islesboro is now located.

Shubael Williams is said to have been the first settler on Islesboro, arriving in 1764 from Stonington, Connecticut. He cleared land and built a log house near what is now called Bounty Cove, mid-point on the island near the Narrows. Other settlers soon followed, including Pendletons, Boardmans, Warrens, Hatches, and Coombs, whose descendants live on the island today. These settlers were a hearty bunch, not only surviving the rigors of pioneer life, but doing so on an island in Maine.

1780 Solar Eclispe Instruments, Islesboro, 1980
1780 Solar Eclispe Instruments, Islesboro, 1980

Item Contributed by
Islesboro Historical Society

During the Revolutionary War, Islesboro was in a vulnerable position, being located directly in a war zone. Islanders were forced to trade with both sides, as a matter of survival, and records show that several island men were conscripted into the British army against their will. British forces occupied Castine, three miles east of Islesboro across the Penobscot Bay, and much of eastern Maine. On August 13, 1779, American and British naval forces clashed, and the Americans suffered a crushing defeat. All thirty-nine ships in the American fleet were either captured, burned or scuttled. The Penobscot Expedition, as it came to be known, remained the worse worst American naval defeat until the bombing of Pearl Harbor in 1941.

Islesboro was still controlled by Great Britain in 1780 and considered “behind enemy lines” when scientists from Harvard determined that a solar eclipse would occur on October 27th, 1780 and the best place to make scientific observations was on Islesboro. Reverend Samuel Williams, Professor of Mathematics at Harvard and leader of the group of scientists who wished to record the eclipse, had to obtain permission from British forces, who eventually granted the party “free passage.” This was to be the first official (recorded) total eclipse in American history. Unfortunately, Williams made a mistake in his calculations and the party was outside “the track of totality,” missing the corona of the eclipse. A bicentennial reenactment of the event by Harvard scientists took place on Islesboro October 27th, 1980.

After the Revolutionary War, General Henry Knox, who served under George Washington as Secretary of the Department of War, began acquiring large parcels of the Waldo Patent, the before-mention tract of land comprising most of present-day Knox and Waldo Counties. General Knox was married to Lucy Flucker, descendant of the Waldo family, and through her inherited a portion of the Waldo Patent. Knox purchased the remaining shares of confiscated land (some of the Waldo family members had made the mistake of remaining Loyalists, and their property was confiscated after the Americans won). By 1793 Knox was the sole owner of the Waldo Patent.

General Knox took an active interest in his newly acquired land, and set about putting his rights in order. Some settlers on Long Island Plantation, as Islesboro was then called, took deeds from General Knox, others did not, especially those living above the Narrows. A controversy quickly arose. The settlers living on the island insisted that the island should not be included in the Waldo Patent, since they believed it lay over three miles off shore. In 1788, islanders sent a petition to the General Court asking for an examination of General Knox’s claim to ownership of the land. Several surveys were conducted by both sides of the controversy, trying to determine the actual distance from shore. The controversy was settled in 1799, in favor of General Knox, who quickly sold off most of the island in 100 acre plots to islanders, many of whom had been living on and developing the island for thirty years.

Warren Survey Map, Islesboro, from a ca. 1799 map
Warren Survey Map, Islesboro, from a ca. 1799 map

Item Contributed by
Islesboro Historical Society

At the same time the islanders were questioning the validity of General Knox’s claim to the island, they also asked that the island (then called Long Island) be incorporated as a town, under the name of Winchester. On January 12, 1789, Long Island, 700 Acre Island, Job’s Island, and the Lime Islands were incorporated under the name of Islesborough (spelling changed to Islesboro on July 10, 1890), not Winchester as originally proposed. The first town meeting took place April 6, 1789.

The War of 1812 proved to be a difficult time for islanders. British ships prowled Penobscot Bay, cutting off supply routes and conscripting men into the British navy. Supplies were at a premium, and to offset high costs, islanders frequently took their produce to Castine to sell to the British stationed there. Approximately seventy families lived on Islesboro at the time. While battles were being fought around them, islanders continued to live as best they could, farming and fishing as they had done since the island was first settled.

Boning Knife, Islesboro, ca. 1800
Boning Knife, Islesboro, ca. 1800

Item Contributed by
Islesboro Historical Society

The earliest settlers lived from the land and sea. They grew their food, raised animals, fished and clammed. Schooners brought supplies to islanders, who shipped surplus produce such as potatoes back to Boston on the same vessels. The first regular packet (small sailing craft) line was established in 1859 between Islesboro and Belfast, bringing supplies to the islanders from a much shorter distance.

Beginning in the spring of 1816, town meetings on Islesboro included discussions of separation from the State of Massachusetts. Based on the voting record, islanders were not initially in favor of the separation. On October 29, 1819, a convention held in Portland created a Constitution of the State of Maine, which gave voting rights to “every male citizen of the United States of the age of twenty-one years and upwards, excepting paupers, persons under guardianship, and Indians not taxed.” Josiah Farrow represented Islesboro at the convention. Back on Islesboro, ten islanders voted for the Constitution, one against. The Constitution was accepted by the majority of Maine voters, and Maine was adopted into the United States of America under the Missouri Compromise of 1820. This arrangement allowed Maine to join the Union as a free state, with Missouri entering a year later as a slave state, thus balancing the number of free and slave states in the nation.

The Schooner
The Schooner "Pendleton Sisters", Islesboro, ca. 1900

Item Contributed by
Islesboro Historical Society

During the first half of the 19th century, shipping and shipbuilding was a significant part of Islesboro’s economy. The Records of the Custom House in Castine show that twenty-five vessels - mostly small schooners - were built on Islesboro between 1792 and 1837. Sixty-nine Islesboro men were listed as sea captains during the 1840s, a large segment of the male population at the time. However, because of its insularity, having a small work force, and lack of lumber, sawmills and woodworking machinery, Islesboro never achieved the same success enjoyed by many mainland boatyards during the later part of the century. One notable exception was the Pendleton family, spanning three generations of highly successful shipmasters, owners and builders, starting with Captain Mark Pendleton (1811-1888) and continuing through his son Fields Coombs Pendleton (1842-1915) and grandsons Fields Seely Pendleton (1870-1923) and Edwin Seymour Pendleton (1877-1936). From 1900 to 1910 the Pendleton Brothers F.S. and Edwin owned the largest fleet of sailing vessels in the United States.

As one can imagine, transportation to and from an island adds another dimension to challenges faced by residents. Many of Islesboro's first settlers owned small rowboats. Circling the island by water was easier than trying to navigate trails prior to the establishment of roads. Horses first came to Islesboro in the early 1800s, purchased primarily by the wealthier residents. Horses were used as the main form of land-based transportation into the 20th century, long after the introduction of automobiles on the mainland. Islanders and vacationers alike got where they needed to go by foot, bicycle or horse. Livery stables were very busy places in those times, frequently called upon by summer residents. Carriages, wagons, buckboards, sleighs, and four-runner sleds were driven by one or two horses.

Dark Harbor Wharf, Islesboro, 1917
Dark Harbor Wharf, Islesboro, 1917

Item Contributed by
Islesboro Historical Society

By the mid-1800s, steamboats were used to transport passengers and freight to the island. Wharves were built at several points on the island for the convenience of these steamers and the islanders. Summer resorts built wharves at Ryder's Cove, Hewes Point and Dark Harbor to accommodate their guests.

Islesboro Town Meeting, 1933
Islesboro Town Meeting, 1933

Item Contributed by
Islesboro Historical Society

On March 14, 1913 the Seventy-sixth Legislature of Maine passed an act to prohibit the use of automobiles on public roads in Islesboro. Many voters, the majority of which were summer residents, had convinced legislators that this law was necessary. The summer community kept cars off the island from 1913 until 1933. They enjoyed the peacefulness of the island, uninterrupted by the noise and hassle of automobiles. Island residents tried many times to repeal the act but failed for twenty years. The act was finally repealed on March 17, 1933.

When the ban on automobiles was lifted, there became a need and desire to transport automobiles across the bay. In the beginning, scows were used for this purpose. The Red Wing was owned and operated by Leroy M. (Lee) McCorison. It fit four passenger cars and crossed the bay in a half hour. The scow transported the first locally owned car to leave the island, which happened to be that of newlyweds going off for their honeymoon. As more and more cars came to Islesboro, the dirt roads became very dusty. The Red Wing brought the first tar truck to the island to oil the roads.

Governor Brann Ferry, Islesboro, ca. 1940
Governor Brann Ferry, Islesboro, ca. 1940

Item Contributed by
Islesboro Historical Society

Very soon, islanders saw the need for a boat that could transport several cars across the bay at a time. The Town of Islesboro authorized bonds to pay for a publicly owned and run ferry system. The Governor Brann was launched at I.L. Snow Company shipyard in Rockland, Maine at 10 A.M on May 19, 1936. The ferryboat was christened by Miss Evelyn Randlett, who was Islesboro High School's valedictorian that year. The new boat began running on June 27, 1936 but it quickly became apparent that the Governor Brann was too small for the traffic, so in February, 1937 it was taken out for two months to be worked on. The addition of twenty-seven feet increased the capacity from ten to twelve cars. The cost for an automobile was $1.00 and the cost for a passenger was $0.25.

On May 29, 1957, an act authorizing ferry service for North Haven, Vinalhaven, Islesboro and Swan's Island was approved. Thirty days later, this act - signed by Edmund S. Muskie - was made into law. The islands’ ferry system was now state owned and operated. The Governor Muskie provided service to the Islesboro for thirty years, transporting twenty-four cars at a time. On December 1, 1987, the Margaret Chase Smith was put into service. It was a state-of-the-art ferryboat and was named after the congresswoman who represented Maine from 1942 until 1973. This ferry is still in use today. For more information on this topic, please visit Water Transportation.

Islesboro also boasts a small airport. Thirty acres of farmland were purchased in the mid-1960s to be cleared and leveled for an airport and airstrip. There was a designated airport manager. More land was bought over time to increase the length of the airstrip as the demands of the island changed.

Gas Station Calendar, Islesboro, 1947
Gas Station Calendar, Islesboro, 1947

Item Contributed by
Islesboro Historical Society

Because transportation was so difficult in the early days, settlements grew up around the island - separate, distinct and independent settlements that had their own stores, schools (please visit Schools), churches, wharves and post offices. The island was divided into three sections: Up Island, consisting of Turtle Head, North Islesboro, Pripet, West Side/Sprague, the Bluff, and Ryder’s Cove/Sabbathday Harbor; Mid-Island, consisting of Guinea, Hewes Point and Mill Creek; and Down Island, or Dark Harbor. The Town Hall was centrally located, and oftentimes, southern islanders would see their northern counterparts once a year at Town Meeting. The fourteen-mile trip from the northern part of the island to the southern end was an all-day journey by horse and buggy. With the legalization of the automobile in 1933, many of these settlements faded away, but remnants exist to this day. For more information on each of these settlements, please visit Early Settlements.

During the Civil War, or War of Rebellion as it was called by the North at the time, many Islesboro men either volunteered, were drafted, paid “commutation” or furnished a substitute for the Union. During the October 17, 1863 town meeting, residents voted to increase the pay to $325 for each man who volunteered to fill Islesboro’s quota of twenty men. In total, Islesboro paid out for bounty $23,097 and furnished seventy-five men.

Seaside Hotel Commemorative Plate, ca. 1900
Seaside Hotel Commemorative Plate, ca. 1900

Item Contributed by
Islesboro Historical Society

After the Civil War, several factors combined that would change the face of Islesboro forever. An expanding economy provided more leisure time for the middle and upper classes, improved railway and steamship lines made Maine more accessible, and many families sought to escape the summer heat of the cities. Bangor was already a summer destination, and adventurous families soon discovered Ryder’s Cove, just across Penobscot Bay. Ryder’s Cove, or Sabbathday Harbor as it was known to early sailors as an ideal place to rest on Sundays, became Islesboro’s first summer community. In 1868, a simple hotel/boarding house was built, which later expanded to accommodate one hundred guests, with modest cottages springing up around it and on the shore. Soon after, Hewes Point became the second summer community, also having a hotel, cottages and wharf.

Second Islesboro Inn, aerial view, ca. 1950
Second Islesboro Inn, aerial view, ca. 1950

Item Contributed by
Islesboro Historical Society

Ryder’s Cove and Hewes Point remained the island’s only summer communities until the arrival of the Islesboro Land and Improvement Company in 1888, which began buying large parcels of farm land at the southern end of the island, in Dark Harbor. In 1890, company owners built a large hotel, the Islesboro Inn, and steamboat wharf to attract potential buyers. Large, expensive lots were sold to some of the wealthiest families in Boston, New York, Philadelphia and St. Louis. These families put up summer “cottages,” mansions that rivaled the finest on the mainland. With the establishment of Islesboro’s summer communities, islanders' jobs shifted from agricultural to service-based, and remain so today. For more information on this topic, please visit Summer Resorts.

Town Hall calendar, Islesboro, 1926
Town Hall calendar, Islesboro, 1926

Item Contributed by
Islesboro Historical Society

Everyday life on Islesboro is like that of most other small communities, except that it is defined by physical boundaries. These boundaries sometimes present challenges that most islanders feel are a small price to pay for the beauty, tranquility and kinship the island has to offer.

When the town of Islesboro (spelled Islesborough at the time) was incorporated in 1789, the first town meeting was held on April 6, 1789 in the home of Shubael Williams. The first Islesboro Town Hall was built in 1804, and was also the Baptist Meeting House. In 1892, the building was replaced in the same location with the second Town Hall and High School. Today, the old town hall is the home of the Islesboro Historical Society, established in 1964.

Second Baptist Church, Islesboro, ca. 1950
Second Baptist Church, Islesboro, ca. 1950

Item Contributed by
Islesboro Historical Society

The first recorded religious meeting on Islesboro took place in 1791, in the barn of Joseph Boardman. These worshipers were Baptists, who built the first house of worship on the island, the Baptist Meeting House and Town Hall (1804). A series of Baptist churches followed, including the Free Will Baptist Church (1843), the Second Baptist Church (1845), and the First Baptist or Middle Church (1853). Christ Church (1893) was built in Dark Harbor by Episcopalian summer residents. St. Mary’s of the Isles (1901) was built for the Catholic summer help who worked for the wealthy summer families. Islesboro’s churches have served a variety of needs of the community - spiritual, cultural, and financial and continue to do so today.

Buggy, Islesboro, ca. 1880
Buggy, Islesboro, ca. 1880

Item Contributed by
Islesboro Historical Society

Another aspect/concern of early and present island life is medical care. In the early days, doctors had to be fetched from the mainland by boat to attend the sick. Southern islanders rowed to Lincolnville, borrowed a team and drove to Camden for a doctor. Northern islanders rowed to Castine for medical help. The earliest known doctor to practice on Islesboro was Dr. John Payne, arriving in 1830 and staying until 1840. A variety of physicians served as Town Doctor, visiting patients in their homes by horse and buggy. When cars were finally allowed on the island in 1933, Dr. William S. Garelcon became the last “horse and buggy” doctor on the island. Over the years, islanders found it increasingly difficult to attract and keep a doctor on the island. In 1982, the town hired its first Physician Assistant, who worked in conjunction with a mainland M.D. to serve the medical needs of islanders.

Post Office Boxes, Islesboro, ca. 1890
Post Office Boxes, Islesboro, ca. 1890

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Islesboro Historical Society

Communication between Islesboro and the mainland remained sketchy in the days before telephones. A mail route established between Islesboro and Lincolnville transferred mail every Thursday via boat, with an unofficial post office established on the island c. 1834. Not until 1892 did islanders receive direct mail service from the federal government. A steamboat set out from Ryders’ Cove every morning at 9:00, picked up mail in Belfast, made a drop at Ryder’s Cove and continued to Hewes Point. By 1916, all mail was dropped at the Lime Kiln Wharf and driven the length of the island by team to the island’s various post offices. Mail service was severely disrupted when the bay froze over in 1918, 1923, and 1934. The mail had to be hauled across by hand sleds or horse and buggy.

Islesboro had four post offices: North Islesborough (established 1880 in Ryder’s Cove), Islesborough (established 1889 in Guinea), Dark Harbor (established 1895) and Pripet (established 1915 for the northern most tip of the island). Prior to 1933, all mailed was delivered by horse and buggy. In 1966 the town built a consolidated post office in a central location, and closed all other existing post offices. Today, mail is brought to the island via the ferry from Camden.

Telephone Switchboard, Islesboro, ca. 1915
Telephone Switchboard, Islesboro, ca. 1915

Item Contributed by
Islesboro Historical Society

Telephones came to the island c. 1890, when a single line was strung between the Islesboro Inn in Dark Harbor and Delmart Hatch’s livery stable, for use by the Inn’s guests. By 1891, three public telephones were installed, one up-island, one mid-island and one-down island. The island switchboard was located in the rear of the Dark Harbor Post Office from 1902 to c. 1915. The switchboard moved to a small house on Pendleton Point Road, where operator Mrs. Charles Philbrick (Mrs. Phil) and telephone repairman husband Charlie lived. Islesboro shut down its switchboard in 1962. Life Magazine sent reporters to Islesboro to document the transition to the dial system.

Being an inhabited island off the coast of Maine, a lighthouse somewhere on the island is to be expected. The Grindle Point Light House was built in 1850 at the entrance of Gilkey Harbor. A keeper lived in the house to keep the lantern lit around the clock. The lighthouse was deactivated in 1935, when a separate electrical tower with a blinker was erected next to the lighthouse. The Town of Islesboro purchased the lighthouse from the government for $1,200, to be made into a museum dedicated to honoring seafaring men from Islesboro. The Sailors’ Memorial Museum is still in existence, welcoming both visitors and residents at the ferry dock, and is one of the few remaining lighthouses were visitors can still climb the stairs to enjoy the view from the top.

Alice L. Pendleton Library, Islesboro, ca. 1945
Alice L. Pendleton Library, Islesboro, ca. 1945

Item Contributed by
Islesboro Historical Society

As with most small towns, Islesboro’s libraries have been an integral part of the community. In 1902, the town appropriated funds to establish the Islesboro Free Library, located on the second floor of the old Pendleton School house. Alice Lavinia Pendleton was the first librarian. The library soon moved to another small building, which also proved inadequate. After concerted efforts by the townspeople and a great deal of fund raising, the new Islesboro Free Library opened its doors January 14, 1918. In 1958, the named changed to the Alice L. Pendleton Library, in honor of the dedicated librarian who served the community for almost 50 years. War memorials of those who served from Islesboro during the Civil War and World War I are located on plaques on either side of the front door. A World War II Honor Roll stood on the grounds of the library for a time, but burned and was not replaced.

The Dark Harbor Library opened in 1900 and served the summer community and residents who lived in the southern part of the island. It was located on the second floor of the Dark Harbor Post Office and supported by the summer community, although it remained open all year. The library closed in 1965 and its books and furniture were donated to the Alice L. Pendleton Library.

Islesboro High School Boys' Basketball Team, 1906
Islesboro High School Boys' Basketball Team, 1906

Item Contributed by
Islesboro Historical Society

There never seemed to be a shortage of entertainment on the island. Both year ‘rounders and summer residents left the island less than today, and created their own fun. Islanders “neighbored” in the winter. Plays, musicals, dances, movies and roller skating were held at Town Hall. In the 1920s, the old Union Hall was renovated and renamed Community Hall. For many years this hall was used for public functions, being centrally located. In 1937, the Rolerson family built the Ocean View Movie Theater. Movies and dances were also held in Dark Harbor at the Pendleton Hall. Balls and concerts were held at the old hotels. High School basketball was extremely popular, and remains so today.

Over the years, many types of organizations have formed on Islesboro to keep its occupants occupied, everything from Free Masons to Girl Scouts. The Dark Harbor summer community formed the Tarratine Club to provide entertainment for the summer residents. The Second Baptist Sewing Circle celebrated its 150th anniversary in 2008. Its members are still working to make this community a better place in which to live.

People have been living on Islesboro for over two hundred years, supporting themselves and their families in a variety of ways. The local economy has shifted from agrarian to primarily service industry. For further information on this topic, please visit Businesses/Cottage Industries and Netting on Islesboro video .

Islesboro, ca. 1957
Islesboro, ca. 1957

Item Contributed by
Islesboro Historical Society

Islesboro is a unique place, wild yet civilized, independent yet close knit, two distinct socio-economic groups co-dependant on each other and living in harmony. Home for some, vacation haven for others, most agree that we are lucky to be part of the island’s on-going history.