A small timeline:
1500s - Klein Venedig settled by thousands of Germans
1600s - New Holland successfully defended by the Netherlands, forces the Portuguese to remain east of the San Fransisco River. UK captures the River Plate, and brings in Hessians, who capture the Uruguay region. It becomes a dependency, free for settlement, if the Germans keep the Portuguese from coming south (OTL: Santa Catarina, Rio Grande do Sul, Uruguay). Taking advantage of the situation is Prussia, which aided the Dutch in exchange for Portugal's African colonies.
1740s - UK captures Cuba and Hispaniola from Spain, flooding them with settlers.
1770s - UK claims New Caledonia when Captain Cook lands on the islands.
1776-83 - US Revolutionary War - Canada, Nova Scotia, Bermuda, and the Bahamas join the revolution. Loyalists flood Cuba, and Southern Canada (Rio de la Plata).
1800s - UK colonies are flooded with settlers to South America, South Africa, Cuba, Australia, New Zealand, and New Caledonia.
1815 - Napoleonic Wars end, and France's colonies are divided up to other nations: Guadeloupe/Martinique to Sweden, St Martin to the United Kingdom of the Netherlands, St Pierre et Miquelon to the United States (which didn't participate, but whose ambassador expressed interest in the islands for the state of Quebec), Reunion and Mayotte to Prussia, St Bart to Sweden, and the Southern Indian Islands to Hanover.
1810s-30s - Anglo settlers push into Texas and the land across the Rio Grande, on invitation by Mexico to settle the land. What will become South Africa is also settled by the Dutch and the British much more intensely than OTL due to earlier gold discovery there, and in Australia.
1820s-30s - US settlers find the Washington Islands and claim them for the US (OTL Marquesas Islands), eventually leading to the colony of American Polynesia (today the territory of American Polynesia)
1822 - Liberia settled by freed slaves from the US. Northern blacks who were free become a large part of the settlers, and begin instructing the freedmen in governance, along with abolitionists from across the north. There is a 10 to 1 black to white ratio in the private colony, which becomes a US colony in 1866 under President Lapointe as part of Lincoln's surviving Reconstruction policy to allow freed slaves either to go to Liberia, or settle west and south.
1831-3 - Klein Venedig declares independence from Spain, becoming the first German-speaking nation in the New World. Its government is modeled on the US to the north, as some Americans did settle here. It begins accepting settlers from Germany, Sweden, Austria, Denmark, Norway, Switzerland, Poland, and even Ireland/Scotland.
1836 - Texas and the Republic of the Rio Grande declare independence from Mexico, and succeed in a short war against it, based on Mexico's violation of its 1823 constitution.
1837 - UK abolishes slavery; begins process of moving former slaves to its colonies in Africa to make room for settlers and to begin a 10-year process of emancipation - instruction in reading, English, trade, and governance.
1846-8 - Mexican-American War - Texas and RG join the US, and Mexico blatantly crosses into US territory to start the war. By war's end, Mexico is forced to cede New Mexico, California, Baja California, Sonora, Chihuahua, and all claims to Texas and the Republic of the Rio Grande.
1861-5 - US Civil War occurs when the South secedes from the Union.
1866-78 - Reconstruction gradually allows the South back into the Union, starting under President Lapointe. President Lincoln's assassination by a former Confederate threatens to embitter the North till Lapoint rallies the nation together. Reconstruction is a much smoother process in this reality than ours.
1898-9 - Spanish American War - US vessel Maine in Puerto Rico draws the US into war with Spain, resulting in the US gaining Guam, Puerto Rico, and the Philippines from Spain.
1900 - German colonies include Samoa, the Caroline Islands, Mozambique-Madagascar, German Southwest Africa (Namibia/Angola), and several others. Of these, the most colonized were the Carolines, GSA, and German East Africa. Both African territories had over 2 million Germans by 1900, and were tightly integrated into the German Empire.
1912-1918 - World War I - Germany belatedly gets in the war after Austria, Hungary, and Greece join. Turkey joins, then Greece flips to the Allies. Mexico joins the Central Powers, hoping to gain back its territory to the north. It invades the states of Rio Grande and Sonora, and tries to invade South California across the gulf, but Americans from Nova Scotia to Yukon and Alaska all rally and prevent the invasion. At the end of the war, Greece regains the rest of the Aegean coast it wanted, and Constantinople, plus Cyprus. France got Alsace-Lorraine, but not the crippling blow to Germany it wanted, leading to a 'stab-in-the-back' myth, fueling its national socialist movement. Germany's Kaiser Henry I rallies the people after the war, leading a reform movement that makes Germany's economy take off in the 20s, while France stagnates. Mexicans are flat out forbidden to enter the US for any reason for the next 20 years, and many Mexicans living there either leave or change their names. German Austria is formed, including the Burgenland and Preßburg.
1935 - Volga Republic is cleansed - the Germans who settled are forced out by Russia, settling in Posen, Silesia, and East/West Prussia. The resettling process caused Germany to lose focus on France, leading to France's surprise attack in the west against Germany.
1939-45 - World War II - France, Spain, Italy, Japan, and Russia form an Axis, leading the world into war. Germany, the UK, and the US form the core of the Allies fighting against the national socialist (fascist) powers. Mexico joins the Axis, and tries again, this time invading Sonora, then veering right into Texas. The US faces its second invasion by Mexico, and promptly faces a three front war. Mexico is defeated in 1944, the first of the Axis to fall. Afterwards, immigration from Mexico, Central America, and Colombia is halted until the 1970s. South Canada, New Holland, New Brandenburg, British Guiana, German Guiana, Surinaam, British Cuba are still allowed to immigrate. Russia flipped sides during the war, allowing it to claim victory in the 'Great Patriotic War.'
1946-8 - US gains huge advantage in rocketry when dozens of German scientists and their research were evacuated from Europe during the war, and most decided to settle in the US afterwards. The US and the UK give Germany debt forgiveness from WW1 and WW2 in exchange for their military, medical, and industrial patents, giving the allies a huge leap over Russia. As part of the Marshall Plan, the US sends billions to rebuild Germany, France, and the rest of Europe from the war. Millions of GIs come home with German, Dutch, Italian 'war brides.'
1948-9 - China War - Russia funds Mao Tse Tung's rebellion against the corrupt Chinese government, while the US, UK, and Australia send both troops and material to the republican opposition. They defeat Mao as a traitor, who's executed, leaving China united, but the Allies force China into a series of government reforms against the corruption it faced over the last 80 years.
1949 - Germany annexes German Austria in a plebiscite, after the US, UK, and German forces providing security for the nation count the overwhelming votes for annexation.
1951-2 - Korean War - Russia has another proxy in Korea, which is defeated by the US/UK/German/Australian alliance. Korea remains united.
1950s - post-war boom in Germany, Australia, New Zealand, South Canada, United States, United Kingdom, Netherlands, and their colonies. The UK, Netherlands, and Germany give their troops massive incentives to settle and build in the colonies, with GI Bills there and in the US to get education, house loans, and car loans. Suburbs grow in the US, South Canada, Africa, and around the colonies. Little Venedig becomes a tropical tourist stop in South America for Canadians to its south, New Hollanders to its east, and Americans from the north, with its stable government, rich oil reserves, and old world charm, mixed with new world flavor. Cuba also strikes an increase in tourism, with its numerous ties to the US, Yucatan, Jamaica, Little Venedig, British Guiana, and other western countries. Some Floridians call it 'South Florida,' to the ire of Cubans, most of whom come from Cornwall, Wales, and Scotland.
1964-69 - East European War - Russia launches an attack on Poland, which spills into Germany, and then drags central and eastern Europe into a war, soon followed by the United States. Russia's tyrannical government is forced from power, and its gulags are exposed to the world, with massive photographic and video evidence of cleansings in the satellite republics.
1968 - New Brandenburg becomes independent from the United Kingdom, joins South Canada (OTL: Argentina, Chile, Paraguay, Uruguay, parts of Brazil). It and New Holland rapidly become the most prosperous, populous, and advanced nations in South America.
1969 - US lands the first man on the moon. It is followed soon by the United Kingdom, then Germany. Russia's space program halted after Sputnik, and manned orbits due to the war, leaving the west far ahead in the space race. With three space powers, though, national pride comes into play with the three nations vying for the next title.
1971-3 - Greco-Turkish War. Turkey invades Greece, attempting to claim Constantinople for themselves, but is turned back by British and American naval forces, which reinforce the Greeks. Greece signs a deal for a series of American military bases and missile installations in Asia Minor.
1972 - UK puts three men on the moon
1976 - US and Germany put men on the moon. First American woman on the moon on August 8th.
1977 - the shuttle Enterprise is launched, and soon converted to space-worthiness
1986 - Challenger explodes, leading to a 2-year grounding of all shuttle flights for re-evaluation
2000 - President Jackson makes it a mission to create an International Space Station, with parts coming from around the world, a truly cooperative venture.
2009 - First components from the US and UK launched - two habitation modules, and a science lab.
2010 - the new shuttle is launched, with upgraded computers and avionics, carrying more cargo and people to space.
2011 - Germany launches its component, with Korea and China using American facilities to launch their components.
2012 - France, Denmark, South Canada, and South Africa launch components with American and British vessels.
2018-2024 - Restoration Wars - due to high spending and debt by all nations, the entire world economy falls apart, nation by nation, when the dollar collapses. Those who fought against such spending, debt, and excessive regulation finally put the world back together, amending many constitutions to reign in spending, deficit spending, and abuses by governments, and other provisions. Socialists, communists, and fascists are angered and disappointed, but can't do anything about it, and leave most western nations for Asia and India.
2051-2061 - World War III, "the Eugenics Wars," fought be genetically engineered 'supermen,' one of whom was Khan Noonien Singh, who conquered a quarter of Earth before his defeat. His Eastern Coalition, "E-Con," would be responsible for over 400 million deaths in Asia alone. Atomic weapons are used for the first time since WW2.
2063 - First Contact with aliens, the Vulcans, by humans.
2071 - United Earth Space Probe Agency formed, based in Cape Canaveral.
2080 - Nations around Earth begin clamoring to build new space ships.
2080-2140 - Great Colonization Race begins, under UESPA coordination. Nations claim certain systems and others agree to recognize them. In all, 24 colony systems are organized. Many use them as 'experiments' where they can try reviving old ways of life or old languages. Genetic experimentation is forbidden, but fertility treatments help the colonists grow quickly. UESPA cedes control when the colony reaches 1 million, and has free, republican government with free elections, and guarantees of basic rights (speech, arms, trial by jury, privacy, search/seizure, parental rights, etc).
2154 - Earth Starfleet launches the NX Class Enterprise, under Captain Archer.
2160-2164 - Earth-Romulan War fought, soon establishing a Neutral Zone between the two powers.
2176 - United Federation of Planets charter is signed after deliberation amongst 13 star systems on Earth.
2223 - disastrous first contact with the Klingons leads to decades of hostility
2245 - USS Enterprise launches under Captain Robert April. He makes dozens of first contacts, and rescues a ship of Orion children, many of whom are adopted on Earth and become Starfleet officers in gratitude.
2264 - Captain James Kirk assumes command of Enterprise
2269 - Kirk's five-year mission ends, and Enterprise becomes the testbed for a refit program to extend the life of the Constitution class
2271 - Admiral Kirk reclaims the Enterprise in an attempt to stop a probe from destroying earth, which turns out to be Voyager 6
2285 - Kirk stops Khan, who captured the Reliant, from using Genesis, but at the cost of the Reliant, and Captain Spock. Kirk then steals Enterprise, returns to Genesis to retrieve Spock and reunite him with his katra. The Enterprise is destroyed to prevent it from falling into Klingon hands, and his crew escape to Vulcan on a Klingon bird of prey. After several months, they start the return to Earth, but a probe is destroying Earth, which they stop by time travelling back to 1986 and rescuing two humpback whales, which communicate with the probe and get it to restore Earth. Kirk's trial takes this into consideration and his punishment is simply a demotion to captain and return to the Enterprise A.
2293 - Klingon moon Praxis explodes, forcing the Klingons to the peace table with the Federation. Kirk stops the peace process from failing when he exposes a plot to assassinate both Gorkon and the Federation President.
2294 - Enterprise B launched, Kirk is lost momentarily, but returns shortly afterward, claiming to have seen a future Enterprise captain. John Harriman remains Enterprise captain.
2335 - Enterprise C launched
2344 - Enterprice C lost defending Narendra III, an important event which leads to the Klingon-Federation alliance.
2364 - Enterprise D launched with Captain Picard at the helm.
2366 - Starfleet gains
new uniforms - jacketed versions of the current uniform reminiscent of those of a century prior.
2367 - Riker promoted to Captain of the USS Titan after the Battle of Wolf 359. Counselor Troi, a blonde-haired, blue-eyed Betazoid (as are all Betazoids), goes with him. Picard inherits Shelby as his new first officer, and a new counselor, Kara Nareth, a full Betazoid.
2371 - Picard encounters Soran, but the Enterprise D stardrive section is heavily damaged in an encounter with a Bird of Prey. Enterprise is refit for a year, with a new bridge, weapons, engines, and is as tough as the new Sovereigns. USS Voyager is lost in the Delta Quadrant.
2372 - Enterprise D participates in First Contact due to a Borg incursion at Earth drawing them into the past. Riker and most of his crew, along with the entire Defiant crew are rescued from the Borg before the temporal incursion, saving both Worf and Troi.
2373 - Voyager is thrown back to the Alpha Quadrant in an errant wormhole event, which also drags the Enterprise into the Delta Quadrant to face Species 8472. Picard is forced to face the Borg again, but both he and Shelby manage to outwit the Borg and stop 8472, with only 1 surviving Borg - 7 of 9. Soon after severing her connection with the Collective, her implants begin to shut down, leading Doctor Crusher to remove most of them (as in our timeline), and though initially Shelby wanted her thrown out of an airlock as a security risk, Picard remembered his time being a Borg, and asked his crew to help her re-acquaint herself with humanity, starting with her real name - Annika Hansen. She tries to return to the Borg once, but after finding hidden memories from the USS Raven, and Data, Shelby, Picard, and the other crew, including Tasha Yar, helping her, she grows to like her human life and appreciate her individuality. She begins to see Picard as a father figure. Dominion War begins this year in the Alpha Quadrant.
2375 - Enterprise returns from the Delta Quadrant using Borg transwarp conduits and a future Enterprise crewman. Enterprise returns to the Alpha Quadrant with numerous first contacts, worlds, plants, and even a few new crewmen/women (the Borg children), close after the Dominion War ends.
2376 - Annika Hansen becomes a Lt JG under Captain Picard, and has her emotional inhibitor safely removed.
2379 - Remans begin a coup on Romulus by Shinzon, a human woman, unbeknownst to the Federation, who lures the Enterprise to Romulus under a flag of peace. It turns out Romulans had cloned dozens of humans under a prior government with the intent of placing them as sleeper agents, but the Tal Shiar scrapped the plan and shipped them to Remus to work in the labor camps. They rebelled and took over the Romulan government. Captain Picard discovers that Shinzon is (genetically) his daughter. He has to stop her before she destroys Romulus with a new warbird, and then starts a war with Earth. Ambassador Spock helps lead a new peace movement with a newly turned Sela Yar (who is surprised to see her mother alive and well on a Federation ship, no less) to rally several ships to help Enterprise stop Shinzon, and show that Romulans and humans can coexist and cooperate. Shinzon is stopped, and Picard has a touching moment with Annika, who tells him she considers him her father.
2380 - Picard becomes an Admiral. Riker assumes command of Enterprise.
2385 - Enterprise undergoes a refit with a third nacelle, phaser cannon, and other upgrades.
2390 - Enterprise becomes Admiral Riker's flagship. Doctor Crusher, after a stint at Starfleet Medical again, becomes captain of a medical ship.
2393 - relations with the Klingon Empire strain and collapse after Species 8472 forces the two sides into a new cold war with each other. Worf sides with the Federation, however.
2405 - Enterprise D retired in a grand ceremony.
2406 - Enterprise E launched.