You can easily watch any of the shows in any order, although there are quite a few callbacks that might miss. It's generally accepted that the first two seasons of every series (except TOS) are terrible, so it's worth keeping that in mind. If you haven't seen the JJ Abrams films, they're probably a good place to start. There may be some small references you might miss, but I personally think they're more enjoyable if you don't have any knowledge of the Trek universe. Otherwise, I'd recommend starting off with either TOS, the second film, or TNG. DS9, VOY and ENT are all heavily reliant on refences to previous series and films, but these are mostly minor bits of fanservice which aren't usually required to understand the plot.
I've written some stuff about each series here. If this all seems overwhelming, then I'd say just start with TOS and work your way through each series/film from there.
The Original Series
This is a good place to start if you don't mind the poor production values and campyness. There are quite a few bad episodes, particularly in the third season, but the first and second are generally entertaining.
Some highlights:
The Next Generation
TNG is a good place to start if you don't want to watch TOS. Although the series has a few multi-episode plotlines, you can pick almost any episode at random and watch it without knowing any of the backstory. Seasons one and two are pretty bad compared to the rest, so I'd recommend watching one or two later episodes first (Darmok or The Inner Light are good choices) just so you can get a good idea of what the show is like at its best.
For season one, I would advise that you only watch three episodes: Encounter at Farpoint, Datalore and Skin of Evil. They have the same level of quality as the rest of season one, but they're important for continuity reasons. If you decide to watch the rest of the season, just remember that it gets much, MUCH better later on.
With season two, avoid Shades of Grey. Otherwise this season is mostly okay. Some important episodes for future storylines include: Q Who, A Matter of Honor and The Emissary
From season three onwards the show becomes much, much better. There are quite a few divided opinions on some episodes, but generally it's agreed that 3-6 have the best episodes. Season seven was weaker, but is still of higher quality than season one.
The films all take place after the series is finished. Generations has some very noticables flaws, but has a major event which affects the later films. If you decide to watch DS9, I recommend seeing this film before you reach Season 4. The rest of the films can easily be watched at any time afterwards, although there are some minor references to DS9 and VOY. If you feel like doing things chronologically, watch First Contact during DS9 season five, Insurrection after finishing DS9 and Nemesis after finishing Voyager. Just be aware that Insurrection and Nemesis aren't as well regarded as most of the other films.
Deep Space Nine
DS9 is less popular than TNG and TOS, but there are quite a few people who prefer it. If you like shows with a multi-episode plotlines and a greater sense of continuity (like Babylon 5 or Battlestar Galactica) then you'll probably enjoy DS9. Like TNG it has a slow start, but unfortunately there are quite a few earlier episodes which are refenced later on. At the very least you can probably skip Q-Less and Move Along Home.
As DS9 first aired alongside TNG seasons 6-7, there are few minor plotlines which are refenced in both shows. You can easily watch DS9 after finishing TNG, but you may want to consider using this guide to watch them in order. It's not essential, but it can be entertaining.
Voyager
VOY is much less well-regarded than the previous two seasons. There are quite a few decent episodes, but the overall quality is lacking when compared to the other series. It does have its fans though, so try it out. Just be aware that, like DS9 and TNG, the first two seasons are not as good as the rest of the show. In particular avoid Threshold, an episode hated even by the guy who wrote it. If you do decide to watch it, I'd say save it for after DS9. It started airing during DS9's third season, but there aren't really any shared plotlines, aside from a brief cameo from Quark in the first episode.
Enterprise
ENT is just as polarizing as VOY, but I personally have a soft spot for it. Again, the first two seasons are full of bad episodes, but seasons three and four were showing a lot of improvement. Like VOY, I'd recommend you keep an open mind and watch it anyway.
I've written some stuff about each series here. If this all seems overwhelming, then I'd say just start with TOS and work your way through each series/film from there.
The Original Series
This is a good place to start if you don't mind the poor production values and campyness. There are quite a few bad episodes, particularly in the third season, but the first and second are generally entertaining.
Some highlights:
- "Space Seed" - Provides the backstory to Wrath of Khan.
- "Balance of Terror" - First appearance of the Romulans.
- "Errand of Mercy" - First appearance of the Klingons.
- "City on the Edge of Forever" - Isn't really referenced in future episodes or series, but it's still a very good time-travel story.
- "Amok Time" and "Jouney to Babel" - Both episodes provide some good backstory for Vulcans and Spock.
- "Mirror, Mirror" - First appearance of the Mirror Universe.
- "The Trouble with Tribbles" - A great episode which is revisited brilliantly by DS9.
The Next Generation
TNG is a good place to start if you don't want to watch TOS. Although the series has a few multi-episode plotlines, you can pick almost any episode at random and watch it without knowing any of the backstory. Seasons one and two are pretty bad compared to the rest, so I'd recommend watching one or two later episodes first (Darmok or The Inner Light are good choices) just so you can get a good idea of what the show is like at its best.
For season one, I would advise that you only watch three episodes: Encounter at Farpoint, Datalore and Skin of Evil. They have the same level of quality as the rest of season one, but they're important for continuity reasons. If you decide to watch the rest of the season, just remember that it gets much, MUCH better later on.
With season two, avoid Shades of Grey. Otherwise this season is mostly okay. Some important episodes for future storylines include: Q Who, A Matter of Honor and The Emissary
From season three onwards the show becomes much, much better. There are quite a few divided opinions on some episodes, but generally it's agreed that 3-6 have the best episodes. Season seven was weaker, but is still of higher quality than season one.
The films all take place after the series is finished. Generations has some very noticables flaws, but has a major event which affects the later films. If you decide to watch DS9, I recommend seeing this film before you reach Season 4. The rest of the films can easily be watched at any time afterwards, although there are some minor references to DS9 and VOY. If you feel like doing things chronologically, watch First Contact during DS9 season five, Insurrection after finishing DS9 and Nemesis after finishing Voyager. Just be aware that Insurrection and Nemesis aren't as well regarded as most of the other films.
Deep Space Nine
DS9 is less popular than TNG and TOS, but there are quite a few people who prefer it. If you like shows with a multi-episode plotlines and a greater sense of continuity (like Babylon 5 or Battlestar Galactica) then you'll probably enjoy DS9. Like TNG it has a slow start, but unfortunately there are quite a few earlier episodes which are refenced later on. At the very least you can probably skip Q-Less and Move Along Home.
As DS9 first aired alongside TNG seasons 6-7, there are few minor plotlines which are refenced in both shows. You can easily watch DS9 after finishing TNG, but you may want to consider using this guide to watch them in order. It's not essential, but it can be entertaining.
Voyager
VOY is much less well-regarded than the previous two seasons. There are quite a few decent episodes, but the overall quality is lacking when compared to the other series. It does have its fans though, so try it out. Just be aware that, like DS9 and TNG, the first two seasons are not as good as the rest of the show. In particular avoid Threshold, an episode hated even by the guy who wrote it. If you do decide to watch it, I'd say save it for after DS9. It started airing during DS9's third season, but there aren't really any shared plotlines, aside from a brief cameo from Quark in the first episode.
Enterprise
ENT is just as polarizing as VOY, but I personally have a soft spot for it. Again, the first two seasons are full of bad episodes, but seasons three and four were showing a lot of improvement. Like VOY, I'd recommend you keep an open mind and watch it anyway.
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