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Colonial Era (1607-1775)
1623: The Province of Maine is established by Ferdinando Gorges and John Mason. Originally, it consisted of the land between the Merrimack and Kennebec rivers in New England.
1628: The Massachusetts Bay Colony is founded.
1629: Gorges and Mason decide to divide their colony between them. The southern portion becomes New Hampshire and the northern portion becomes New Somersetshire. The Carolina colony is formed as normal.
1634: The colony of Maryland is established.
1635: John Winthrop the Younger founds the Saybrook Colony.
1636: Connecticut and Providence Plantations colonies are created.
1637: Ann Hutchinson founds the Portsmouth Colony in OTL Rhode Island. However, this settlement never merges with Providence Plantations and instead remains a separate entity.
1638: The New Haven Colony is founded.
1638 - 1640s: In the OTL, New Somersetshire and Saybrook colonies both run into difficulties around this period leading to their eventual failure and absorption into Massachusetts and Connecticut, respectively. Instead, New Somersetshire attracts settlers to its shores and survives along with New Hampshire. Saybrook is also rather popular among Parliamentarians fleeing during the early years of the English Civil War.
1653: The Parliamentarians win the English Civil War and form the Commonwealth in mostly the same way as normal. However it is much more successful and was also more involved in the colonies, especially favoring some colonies in New England.
1655: Saybrook is given recognition by Oliver Cromwell's Commonwealth government.
1658: When Cromwell dies his son Richard becomes Lord Protector.
1659: Richard resigns and allows his more competent younger brother Henry to take his place because people didn't want the Protectorate to die. Charles II remains in exile.
1664: Britain captures the Dutch colony of New Netherlands, creating New York, New Jersey and Delaware.
1665: Separate charters are granted to Connecticut and New Haven.
1674: Henry Cromwell dies in March. Charles II returns from Spain and assumes the throne.
Colonial developments in the rest of the 17th century and up until the American Revolution happen mostly the same as OTL.
American Revolutionary War and Early America (1775-1797)
1775: American frontiersmen in the Appalachians including Daniel Boone defy the Proclamation of 1763 by settling in the unrecognized colonies of Transylvania and Westsylvania.
1776: The United States declares its independence from Britain.
1777: In addition to the larger conflict taking place, there are also skirmishes between New Hampshire and Vermont Republic, and Grafton county in the north of the state begins to think of itself as separate from New Hampshire.
1782-1783: The southern theatre of the war and Yorktown campaign was assisted slightly by troops under the command of Colonel Thomas Michelson which arrived from Transylvania. The war ends and Treaty of Paris as normal.
1784: Although Virginia did not claim land to the west of the Appalachians North Carolina did and ceded it to the government. However, a portion of the land declared its independence as the state of Franklin. The Confederation government also worked on resolving the territorial dispute between Connecticut and Pennsylvania by creating the State of Westmoreland.
1786: The State of Franklin joins the United States.
1787-1790: The Constitution is written and ratified by the states with Delaware, Pennsylvania, New Jersey, Westsylvania, Transylvania, Franklin, Providence Plantations, Georgia, Connecticut, Massachusetts, Maryland, South Carolina, New Hampshire, Virginia, New York, Westmoreland, Grafton, North Carolina, Plymouth, Saybrook, Rhode Island, New Somersetshire, and New Haven, the nation has 23 states. Article Four, Section Three of the Constitution reads "New States may be admitted by the Congress into this Union; but no new States shall be formed or erected within the Jurisdiction of any other State; nor any State be formed by the Junction of two or more States, or parts of States, without the Consent of the Legislatures of the States concerned or of the Congress". George Washington is elected and the District of Columbia is established. The American Flag has 18 stripes and 23 Stars.1791: The Republic of Vermont joins the Union, but a few small towns along the eastern side of the Connecticut river join the new state.
1796: Tennessee becomes a state. John Adams wins the presidential election and is inaugurated the next year.