Begins and ends with: Star Trek Enterprise seasons 1-4
About a century before the Original Series takes place, Captain Jonathan Archer leads Earth's first steps into the wider universe.
Begins with: 'The Cage'
Ends with: Star Trek: Generations (opening sequence)
For many the most familiar era of Star Trek, featuring Kirk, Spock and the classic Enterprise crew.
The latest point we've seen (so far) in the 23rd century era was James T Kirk being taken away by the Nexus ribbon in the prologue of Star Trek: Generations. This is the event that allows Kirk to meet Picard as the Next Generation crew take on the mantle of headlining the movies.
The first two seasons of Star Trek: Discovery work as a prequel to the Original Series (they even feature a younger version of Spock), but it'll be all change in season 3, after the season 2 finale saw the crew traveling to the distant future to explore a new frontier...
Begins with: Star Trek: The Next Generation (seasons 1-5)
Ends with: Star Trek (2009) – Prime timeline sequences
The richest, most complicated period in Star Trek chronology. During the Next Generation era, Star Trek was experimenting with the idea of a shared universe years before Marvel got in on the act, with three TV shows and four movies interweaving through the same timeline – Voyager's Captain Kathryn Janeway even shows up in Star Trek: Nemesis as a newly promoted admiral.
In the list above, we've shown how the movies (roughly) fit into the chronology of The Next Generation, Deep Space Nine and Voyager.
Begins with: Picard
Ends with: ???
Aside from the destruction of Romulus in JJ Abrams’ Star Trek (2009), Star Trek: Picard gives us our first post-Star Trek: Nemesis look at what the United Federation of Planets has become.
Begins with: Star Trek: Discovery season 2 (finale)
Ends with: ???
In order to save the galaxy, the brave crew of the USS Discovery set off on a one-way mission 900 years into the future in Star Trek: Discovery's season 2 finale. Their 32nd century destination is new territory for Star Trek – Michael Burnham and her crew really are going where no one has gone before in the upcoming season 3.
cf. https://www.techradar.com/how-to/how-to-watch-star-trek-in-order