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A Guide to Trek, from the RPGs: 4. Timeline: A History of the Future
Note that the timeline focuses on major political/military history up to the eras of TNG/DS9/VOY; I haven't summarized the major events of DS9 and Voyager yet, but I'll come back and edit it in if need be. (I also haven't included the timeline of events from Enterprise, as they don't quite jibe with the rest of the canon history, but I can write it up if people want.)
For reference, the Enterprises:
NX-01: From Enterprise, NX-class, captained by Archer.
NCC-1701: From TOS and movies I-III, Constitution-class, captained by Robert April, Christopher Pike and James T. Kirk. (In AOS movieverse, captained by Christopher Pike and then James T. Kirk in Star Trek, Into Darkness, and Beyond.)
NCC-1701-A: From movies IV-VI, Constitution-class, captained by Robert April, Christopher Pike and James T. Kirk. (In AOS movieverse, commissioned/built at the end of Beyond and presumably captained by James T. Kirk.)
NCC-1701-B: From Generations, Excelsior-class, captained by John Harriman.
NCC-1701-C: From the TNG episode ‘Yesterday’s Enterprise’. Ambassador-class, captained by Rachel Garrett.
NCC-1701-D: From TNG and Generations, Galaxy-class, captained by Jean-Luc Picard.
NCC-1701-E: From First Contact, Insurrection and Nemesis. Sovereign-class, captained by Jean-Luc Picard.
Timeline
1992-1996: Eugenics Wars on Earth
2053: World War III
2063: Cochrane’s Phoenix breaks the light barrier; first contact with the Vulcans. Setting for Star Trek: First Contact.
2066: First contact with Alpha Centauri, three way alliance with Vulcans.
2103: Humans fully colonise Mars.
2103+: National conflicts on Earth jeopardise alliance, Vulcan embassy closes.
2113: Founding of New Earth Republic
2150: Final country joins New Earth Republic
2151: NX-01 Enterprise launched.
2151-2155: Setting for Enterprise. (NX-01 mission ran until 2161.)
2156-2160: Earth-Romulan War
2160: Terran Conventions held to draft Articles of Federation
2161: Incorporation of the United Federation of Planets.
2161-2199: New World Economy economic system forms, money no longer required.
2218: First contact with the Klingon Empire (went v. badly.)
2223-2242: Klingon-Federation conflict/war
2233: Alternate Universe: Narada vessel appears and destroys USS Kelvin
2245: Enterprise-A launched; a five-year mission under Capt. April, then ten years under Capt. Pike.
2253: The Axanar Rebellion.
2258: Alternate Universe: Destruction of Vulcan by the Narada; setting for Star Trek XI
2264-2269: Setting for Star Trek TOS.
2266: Discovery of Romulan cloaking technology.
2267: Organian Peace Treaty between the Federation and the Klingon Empire
2273: Setting for Star Trek: The Motion Picture.
2285: Setting for Star Trek II: The Wrath of Khan and Star Trek III: The Search for Spock.
2286: Setting for Star Trek IV: The Voyage Home.
2287: Setting for Star Trek V: The Final Frontier.
2293: Khitomer Peace Accords, demilitarisation of the Klingon Neutral Zone; setting for Star Trek VI: The Undiscovered Country.
2311: Tomed Incident (Federation/Romulan battle); Treaty of Algeron signed, reaffirming the Neutral Zone; Federation agrees not to research cloaking technology
2335: First contact with Cardassians
2344: Enterprise-C rescues Klingon outpost at Narendra III
2347: Cardassia attacks the Federation
2352: Klingon/Federation alliance forms
2363: Launch of the Enterprise-D
2364-2370: Setting for Star Trek: The Next Generation.
2364: First contact with the Q Continuum and the Ferengi
2365: First contact with the Borg
2367: Battle of Wolf 359 against the Borg
2368: Klingon Civil War
2369-2375: Setting for Star Trek: Deep Space Nine.
2371: Setting for Star Trek: Generations.
2371-2378: Setting for Star Trek: Voyager.
2373: Setting for Star Trek: First Contact.
2375: Setting for Star Trek: Insurrection.
2379: Setting for Star Trek: Nemesis.
2387: Romulus destroyed by Hobus supernova.
Note that the timeline focuses on major political/military history up to the eras of TNG/DS9/VOY; I haven't summarized the major events of DS9 and Voyager yet, but I'll come back and edit it in if need be. (I also haven't included the timeline of events from Enterprise, as they don't quite jibe with the rest of the canon history, but I can write it up if people want.)
For reference, the Enterprises:
NX-01: From Enterprise, NX-class, captained by Archer.
NCC-1701: From TOS and movies I-III, Constitution-class, captained by Robert April, Christopher Pike and James T. Kirk. (In AOS movieverse, captained by Christopher Pike and then James T. Kirk in Star Trek, Into Darkness, and Beyond.)
NCC-1701-A: From movies IV-VI, Constitution-class, captained by Robert April, Christopher Pike and James T. Kirk. (In AOS movieverse, commissioned/built at the end of Beyond and presumably captained by James T. Kirk.)
NCC-1701-B: From Generations, Excelsior-class, captained by John Harriman.
NCC-1701-C: From the TNG episode ‘Yesterday’s Enterprise’. Ambassador-class, captained by Rachel Garrett.
NCC-1701-D: From TNG and Generations, Galaxy-class, captained by Jean-Luc Picard.
NCC-1701-E: From First Contact, Insurrection and Nemesis. Sovereign-class, captained by Jean-Luc Picard.
Timeline
1992-1996: Eugenics Wars on Earth
2053: World War III
2063: Cochrane’s Phoenix breaks the light barrier; first contact with the Vulcans. Setting for Star Trek: First Contact.
2066: First contact with Alpha Centauri, three way alliance with Vulcans.
2103: Humans fully colonise Mars.
2103+: National conflicts on Earth jeopardise alliance, Vulcan embassy closes.
2113: Founding of New Earth Republic
2150: Final country joins New Earth Republic
2151: NX-01 Enterprise launched.
2151-2155: Setting for Enterprise. (NX-01 mission ran until 2161.)
2156-2160: Earth-Romulan War
2160: Terran Conventions held to draft Articles of Federation
2161: Incorporation of the United Federation of Planets.
2161-2199: New World Economy economic system forms, money no longer required.
2218: First contact with the Klingon Empire (went v. badly.)
2223-2242: Klingon-Federation conflict/war
2233: Alternate Universe: Narada vessel appears and destroys USS Kelvin
2245: Enterprise-A launched; a five-year mission under Capt. April, then ten years under Capt. Pike.
2253: The Axanar Rebellion.
2258: Alternate Universe: Destruction of Vulcan by the Narada; setting for Star Trek XI
2264-2269: Setting for Star Trek TOS.
2266: Discovery of Romulan cloaking technology.
2267: Organian Peace Treaty between the Federation and the Klingon Empire
2273: Setting for Star Trek: The Motion Picture.
2285: Setting for Star Trek II: The Wrath of Khan and Star Trek III: The Search for Spock.
2286: Setting for Star Trek IV: The Voyage Home.
2287: Setting for Star Trek V: The Final Frontier.
2293: Khitomer Peace Accords, demilitarisation of the Klingon Neutral Zone; setting for Star Trek VI: The Undiscovered Country.
2311: Tomed Incident (Federation/Romulan battle); Treaty of Algeron signed, reaffirming the Neutral Zone; Federation agrees not to research cloaking technology
2335: First contact with Cardassians
2344: Enterprise-C rescues Klingon outpost at Narendra III
2347: Cardassia attacks the Federation
2352: Klingon/Federation alliance forms
2363: Launch of the Enterprise-D
2364-2370: Setting for Star Trek: The Next Generation.
2364: First contact with the Q Continuum and the Ferengi
2365: First contact with the Borg
2367: Battle of Wolf 359 against the Borg
2368: Klingon Civil War
2369-2375: Setting for Star Trek: Deep Space Nine.
2371: Setting for Star Trek: Generations.
2371-2378: Setting for Star Trek: Voyager.
2373: Setting for Star Trek: First Contact.
2375: Setting for Star Trek: Insurrection.
2379: Setting for Star Trek: Nemesis.
2387: Romulus destroyed by Hobus supernova.