1620

Pilgrims Land at Cape Cod and begin settlement of the Plymouth Colony.

1632

Settlement called Machigonne is established at what will later be called Portland, Maine.

1652

The Casco Bay area including Little Sebascodegan Island becomes part of the Massachusetts Bay Colony.

1658

The settlement of Machigonne is renamed Falmouth.

1672

Settlers in the Casco Bay region had essentially evacuated the area by this time due to Indian uprisings.

1675

Start of King Phillip's War (First Indian War) caused by retaliation for the deaths of the Indian, Squanto's wife and infant daughter.

1676

Indians attack Jewell's Island. Settlers escape to Boston.

1678

End of King Phillip's War.

1680

Little Sebascodegan Island is part of the area incorporated as a plantation to be called North Yarmouth.

1690

Four to five hundred French and Indian canoes cross Casco Bay to and destroy Fort Loyall at Falmouth.

1722

Start of Lovewell's War (Second Indian War). Supported by the French in Quebec, this Indian War probably caused more trouble to the people in Casco Bay and Little Sebascodegan Island than any other. Many bay area settlers were killed or  1726 End of Lovewell's War.

1733

North Yarmouth Plantation is incorporated as a town in the district of Maine in the colony of Massachusetts.

1743

Richard Jaqueth purchases 100 acres of Little Sebascodegan Island.

1744

Start of King George's War (French and Indian War).

1745

A call goes out for men to serve in an expedition to Louisburg, Nova Scotia against the French garrison there.

1748

Little Sebascodegan Island is owned by Elisha Cook of Boston and William Tailer of Dorchester.

End of King George's War (French and Indian War).

Joseph Orr purchases Little Sebascodegan Island from the heirs of Cook and Tailer and moves to the island with his brother Clement. They begin cutting and transporting cord wood to Boston.

1751

Michael Sinnett arrives in America (21 years old) and is indentured to Joseph Orr.

1754

Start of the French War (French and Indian War).

1756

Michael Sinnett has finished his indenture and marries Molly Ward. They move to Sheepscott soon after.

1758

Harpswell is incorporated as a town.

Michael Sinnett is impressed into the English Army to fight the French near Quebec.

1760

Byles, an heir to William Tailer, who had not signed off when Orr purchased the land.

This tenth is known as "Byles" and is near Devil's Back and the Orr's Island Bridge.

1762

Will Black moves across "Will's Gut" and takes residence on Orr's Island.

1763

End of the French War (French and Indian War).

1764

Michael Sinnett returns from Quebec. He sells his property at Sheepscott and returns to Orr's Island where he purchases 30 acres from Joseph Orr. Eight homes were eventually built on this land, Michael's own house as well as those of Geo. Sinnett, Isaac Farr, Edward Farr and Royal Graves.

Joseph Orr builds a large blockhouse somewhere near the middle of the island. There are two locations thought to be where the blockhouse was built. Wilson's point near the Joseph Orr (Kittridge) House and a spot just across the road from the Clement Orr House.

1775

Start of the Revolutionary War.

1776

The "Aunt Roxy House" is built by the Reed brothers at the entrance to Bayview road.

1779

All male residents of Harpswell over 16 years old must take an oath of allegiance to the United States. All who refuse will be disarmed.

1780

The first Wilson settles on Orr's Island.

1782

Revolutionary War ends.

1786

Falmouth is renamed Portland.

1789

A resolve on the petition of the residents of Brunswick and Harpswell permitting them to construct a bridge at Hall's Gurnott between the town of Brunswick and Sebascodegan Island provided the bridge is not less than 20 feet wide and be free without towl or tribute.

1792

Residents of Harpswell vote for separation from Massachusetts in January and vote against it in May.

1797

The town again votes against separation from Massachusetts.

1800

Michael Sinnett dies.

Henry Green Settles on Orr's Island.

Linscotts arrive on Orr's.

The main part of the "Pearl House" is built for Simeon Orr consisting of four rooms, two over two.

The Wilson Homestead is built on the bayview by the Reed brothers. The original house was a twin to the "Aunt Roxy House".

1815 c.

The Gilliam family moves from Great Island to Orr's.

1819

In July, Harpswell votes against separation from Massachusetts and in December the vote is for separation.

1820

The present Clement Orr house is built. Prior to this the home was a small log house located about 200 feet north of the present house.

Maine separates from Massachusetts.

1821

The road on Orr's Island is accepted as a town road.

1833

In Nov. the town of Harpswell is petitioned to see if it will build a bridge and lay out a road from the N.E. end of Orr's Island to the grate island. The town refuses.

1834

Because of their "Hostility" over the proposed bridge to Great Island, the town is asked to lay out a road with a public landing at the northwest end of Orr's Island for use as a way to cross the bay. This appears to also have been refused.

1837

The town is again asked to lay out "an open way from Mr. John Wilsons across the tidewaters onto the 'grate island'.

1844

William Stevens comes to Orr's Island.

1845

Wayside Harbor is built. (the present home of Tim Vail).

1852

Some time between 1837 and 1852 the Orr's Island Bridge is built by Orr's Island residents and the town is petitioned in June of 1852 to see if it will accept the bridge and keep it in repair. It is apparently turned down.

1855

The Orr's Island Bridge is again laid before the town for it's acceptance as it is "...without any legal means of support". This time the petition appears to have passed. It is signed by Wm. A. Sylvester, Dunning Orr, Ralph Johnson, Arthur Reed, Charles Reed, William Orr, Charles H. Orr, William D. Orr, Thos. Lanford Jack, Joseph D, Wyer, William Barstow, George Sinnett, Michael Sinnett, Ralph Johnson II, Isaac Littlejohn, and George Orr.

1857

The Orr's Island Bridge is destroyed by vandals. It is rebuilt soon after.

1859

Sylvanus Cushing Prince moves from Brunswick to Orr's Island and marries into the Sinnett family.

1864

Sylvanus Prince and Samual Smullen build Smullen and Prince General Store on the west side of Princes Point.

1865

A petition is submitted to the town for what becomes known as "The Bayview road". This road is petitioned for again in 1894.

1868

Orr's Island Post Office is established. Samual Smullen is the first Postmaster. Mail arrives by stagecoach form Brunswick.

1872

A Petition for a road from "...near Thomas Alexander to A.B. Alexander" is submitted to the town. The town appears to have denied this petition for what later becomes known as "Grassy Road".

1875

Clement Skolfield adds an ell and other changes to the "Pearl House".

1878

The Methodist Episcopal Church is built on the south side of the cemetery, on land given by Charles Perkins.

A petition is again presented to the town for "Grassy Road" It apparently passes this time as it is not petitioned for again.

1882

Moses B. Linscott petitions the town to allow a fish weir at Lowell's Cove. The license to be given to Moses B. Linscott, Frank Mounfort, and James Huff.

1885

Union Church is built north of the cemetery.

Steamboat wharf is built to the north of Prince and Danials General Store. The steamer "Gordon" makes the first scheduled run to Orr's Island with James Long as Capt. Mail service for Orr's and Bailey Islands changes. The mail now arrives via steamer from Portland to the Orr's Island office. Bailey Island didn't have a suitable wharf for the steamboat or mail delivery until 1887 when Lendall York built a coal pocket at Lowell's Cove.

The town is petitioned to lay out a road to Little Island.

1889

The Lowell's Cove road is laid out.

Between June 1889 and November 1890 the town is petitioned five times to provide a road from the Orr's Island Steamboat Wharf to the Main Road.

1890

William Reed builds a house near the north end of Grassy Road which will later be the office for the T- Ledge Girls Camp.

1892

A bridge between Orr's and Bailey Islands is first proposed.

Jeremiah Shea builds the "Stone House" for Justin Varney. This house is inspired by a stone house that Jeremiah has built on Little Island for himself.

1894

The Bayview Road is petitioned for to the town.

1895

Work begins on the Orr's Island Episcopal Chapel.

1896

Willing Workers Circle is formed to promote social and financial interests of the Methodist Church.

1897

The "Hacker Cottage" at Princes Point is built by Edward Hacker.

1898

The "Merritt House" opens.

Charles F. Brown has bought the William Reed house (T-Ledge Camp Office). He opens a boarding house.

1900

The Orr's Island Library is organized in the back room of a store across from the Orr's Island Methodist Church.

Building of the Orr's Island Episcopal Chapel is completed.

1904

The Gurnet Steamboat Co. begins connector service with the Harpswell line from Bailey Island to Gurnet Landing with stops at the Orr's Island wharf on Princes Point and Wilson's Landing at Reed Cove.

1905

A new building is built for the Orr's Island Library.

The New Meadows Steamboat Co. begins runs from Bailey Island to Lowell's Cove on Orr's, then to Cundy's Harbor, Sebasco and Gurnet Bridge Landing.

1906

The Orr's Island Methodist Church is moved to it's present location onto land purchased from Sylvanus Prince.

1908

Capt. Charles Morrill has a home built just north of the "Stone House".

The "Memorial Cottage" is built near the Episcopal Chapel.

1917

World War I begins for the United States.

A petition to the town for a road from the north end of Lowell's Cove to the town way west of Hiram Orr. This became the Lane Road.

1918

World War I ends.

1920

A KKK chapter organizes on Orr's Island.

1925

The KKK holds a 4th of July picnic at Johnson Point. This was the start of the decline of the Clan in this area.

1926

The state and town approve construction of a bridge across "Will's Gut" linking Orr's Island and Bailey Island.

1927

T-Ledge Girls Camp opens at Brown's Corner with Nell Knorr as owner and director.

1928

The Bailey Island Bridge is completed. The only one of it's kind in the world.

Harv Black's store at Robinson's Corner is destroyed in a fire.

1930

The KKK has died out.

A new half mile stretch of road has been opened between Gun Point Church and the Orr's Island Bridge. The new road, begun in the fall of 1929, leaves Gun Point Road and goes over the mountain coming down near the bridge. The entire half mile was blasted and laid out with wide turns for safety.

1933

The play "No Account David" was given at the Redman's Hall. Taking part were Laura Johnson, Eva Van Emberg, Elizabeth Linscott, Edna Wilson, Joe Shea, Roy Gilliam, Robert Johnson, Jere Shea and James Shea. Billy Durgin's orchestra of Brunswick played for a dance that followed.

1934

A new bridge is built between Orr's Island and Great Island to replace the old wooden double span.

1935

The residents of the Little Island area of Orr's Island petition the town to spend $100.00 on new railings and repairs to the Little Island Bridge.

1936

Capt. Charles Morrill of Orr's Island, has had a bathroom installed in his home.

Ben Harris is employed cutting wood for Henry Allen.

Brunswick Fire Dept. is called to a fire at Redman's Hall.

At a special town meeting, $2500.00 was appropriated to continue the road work of the W.P.A. project on the island.

1937

15 men have been added to the W.P.A. project reconstructing the road on the northern end of Orr's Island.

Jack Prince of Orr's Island is building an ice house with a capacity of 100 tons. (WHERE)

1938

Phil Linscott, with the town tractor, has been stationed on Tower Hill to aid motorists, as that section of the road has been nearly impassable with mud for several days.

1941

World War II begins.

1945

World War II ends.

1947

The Merritt House on Orr's Island is sold.

Transfer of property: Sam Nickas of Hartford, MD., and Thimistolokles Hrisikos of Brunswick TO James Stamutis and Charles Sevastellis of Chelsea, MA.

1948

Edwin E. Chase proprietor of Lowell's Cove market will quit the grocery business as of Nov. 1 to concentrate on wholesale and retail fish, lobster and marine supplies. A new wharf is under construction on Mr. Chase's property adjacent to the present market.

1950's

Redmans Hall is sold and proceeds are divided between 60 members.

1966

The Homeworkers Circle of the Methodist Church is disbanded.