After being gone from it since Star Trek Enterprise, my wife and I got back in with Star Trek Lower Decks (oddly enough). If you can handle it being animated (and goofy), it is actually a very dearly written love-letter to TNG and some of the most important moments in Star Trek lore. We appreciated that it didn't try to reinvent characters that already exist, and did a good job of bringing on old actors for cameos. They bring on people from TNG, Deep Space Nine, and Voyager all the time to reprise their roles.

There's a live-action Star Trek currently running that I can't attest to, but it has a crossover with Lower Decks that means I'm going to give it a try.

A quick rundown of what is out there:

TOS - the original series - I don't think it holds up too well, only watch if you get into Trek.

Suggested episodes - trouble with tribbles and balance of terror

TNG - the next generation - the basis of modern Trek. Probably what most people think of with star Trek

Eps - measure of a man, darmok, inner light and cause and effect

DS9 - deep space nine - my favorite, the story of the dominion war and the fate of cardasaia. It has a slow start but really picks up

Eps - duet and in the pale moonlight

VOY - voyager - I'm not a fan but it's popular, jerri Ryan and Robert Picardo are the best parts of the show

Eps - year of hell pts 1&2

ENT - enterprise - it's been a long road getting from there to here, but your time is finally here. It's campy and bad, but I love it. Go in with low expectations and come out with a love of Shran.

Eps - not going up suggest any, quality tends to trend upwards over the course of the show, but there isn't any one episode that highlights anything good about the show.

DISCO - discovery - the start of nutrek. It isn't as bad as some people say, but it isn't great. There are some good characters, I like Tilly, some neat twists and callbacks (Lorka) but on a whole it's just meh.

Eps - none for DISCO every episode builds towards a season arc pretty directly, so it's not good to watch out of order

Picard - it's bad. Season 3 is better if you are a big fan of TNG, DS9 and VOY, as an entry point it's awful.

Eps - I didn't enjoy any enough to recommend

LD - lower decks - funny animated star Trek. I think it's great, but very referential to old series. Not a good jumping on point.

Eps - wej Duj and much ado about Boimler

SNW - strange new worlds - still running and great. An excellent jumping on point, pretty and well acted

Eps - ad astra per aspera and the Elysian Kingdom

to get back into Star Trek I would recommend either Strange New Worlds or Lower Decks. Strange New Worlds is Star Trek heart and soul. Lower Decks is a comedy but also does a great job capturing the heart and soul of Star Trek.

Many of us feel the impulse to recommend whichever Trek first pulled us in. Others are completists or like to get everything in release or chronological order.

I see lots of recommendations starting along these lines here. That might not best for you OP. I’ve had the personal experience of watching everything in first run in release order, but I don’t know if I would attempt that if I were wanting to break back in after a long hiatus.

If you liked the original 1960s show (TOS) with Kirk, Spock and McCoy, Strange New Worlds may be your best entry point now. It takes place on the original Enterprise under an earlier captain, 10ish years before the time of the original show. Kirk and Spock are the same people you know but younger, and necessarily played by new actors. It’s designed to be a gateway show for fans who’ve never seen any Star Trek so you won’t be lost trying to figure out where things fit in. (The movies with Chris Pine as Kirk are set in a separate universe.)

If you were a Next Generation fan, then you might wish to start with Picard season three or Lower Decks.

Start with The Next Generation, just remember the first two seasons are the weakest by far. Really picks up in S3/4.

Then do DS9 and Voyager. Enterprise is worth watching if you get there.

Or start watching Strange New Worlds, it's freaking awesome and modern but has the same feel as old Trek.

We have a guide for just that!

Strange New Worlds is a great starting point. SNW is set in the 5 year mission before Kirk's 5 year mission on the enterprise. There are some arcs that you might not get but it's not necessary to know what the episode is about because it is episodic. I watched the corresponding TOS / Discovery episodes with Captain Pike after I watched the SNW episodes to fill in the parts that I really didn't get but here is a list of the episodes I watched.

The Menagerie Part 1 and 2 (TOS) -> Through the Valley of Shadows (DIS) -> A quality of Mercy (SNW) -> Balance of Terror (TOS)

Picard season 3 is an absolute must if you watched next gen / DS9. For the whole season to make sense you'll probably want to watch the last 2 seasons of DS9. If you watch the last 2 episodes of picard season 3, watch TNG's best of both worlds part 1 & 2, All good things... (the series finale), and Voyager's Endgame (the series finale) it'll make more sense.

the last 2 seasons of DS9 is very political and heavy but many people say it's the best trek - however now SNW is getting close to taking the title.

Watch season 3 of Picard

I would recommend skipping TOS as a show, and reading the James Blish adaptations of it and TAS. They're great stories, but getting various production design and execution issues out of the way is IMHO a good idea. Maybe watch some of the classic episodes like Shore Leave City on the edge of forever The trouble with tribbles

Then watch the original 6 movies - these are pretty good and varied. (except ST V, which... you can skip, or watch if you're a completest or take as an alternate story, or whatever.) TMP is a little slow, and unique, but I think if you're into general sci fi, and are ok with it not exactly feeling like "Star Trek", it's quite good and sets up Spock a little.

Then TNG, DS9 are both quite good, though DS9 really ends up being arcs of arcs for the last few seasons, so you can't dip in and out the same way you can with TNG or TOS.

TNG Movies are with hindsight and time ... ~~~ average? OK?

Generations is generally panned, I think it was basically another episode of the series with a bigger budget, and a middling one at that. First Contact is fun, but don't think too hard. Insurrection is like Generations - I enjoyed it as it was, but it kind of re-made an existing TNG episode, and meh. Nemisis sets up the Picard show, but both are generally so bad that I can't really recommend it.

Honestly, Voyager is flip a coin. I watched it once - first run on air, never have been interested in going back for a rewatch, and doesn't really set up anything for future shows / makes some parts of future shows worse because of how much they screw up in the future shows.

Hot Take, Enterprise is worth watching, and I think air order works better here. Again, they can't help themselves but "ruin" some earlier episodes / stories from TOS / TNG because of fan easter eggs or whatever, so - watching it later as it aired makes it so you get what they're winking about. It also helps answer some lingering questions from other shows (if you care for that) in the 4th season. I will warn you, it's probably a straight average 5/10 so there's some lows, and very few highs - most episodes are ... OK. Then again, if you can get through TOS and TNG lows, you'll be fine here.

I think you can skip the 09 reboot series of movies, unless you really like JJ Abrams, lens flare, or some of the actors (or are a completest). Looking back, they're entirely forgettable and not that great sci fi action films.

Looking back, I'd take a hard pass on Discovery and S1 and S2 of Picard, unless you like pain and screaming at the TV (assuming you actually liked TNG and 90s trek). S3 of Picard is OK, IF you're super jonesing for more TNG no matter what. But really, TNG should have ended with All Good Things and left it there - that was a PERFECT ending, and they keep trying, and failing, to improve on it IMHO. So far, you can skip S3 of Picard and not have it affect anything else.

Lower Decks is surprisingly really really really good. Watch it.

Strange New Worlds is actually decent - and feels a lot like TOS in terms of episodic, random ups and downs in both good and embarrassingly bad episodes. It's another prequel, but again, I think watching in air order makes sense - especially as it's still airing new episodes, you can't watch it first really.

I took a pass on Prodigy - opinions are mixed, and future availability and new seasons seem up in the air. It's also a kids show from what I gather. I tried the first episode and was like - nah, not for me.

"Star Trek" homages - watch Galaxy Quest - that's amazing. The Orville S1 and S2 are really good TNG. S3 changed and I did not like it as much, and dropped it part way through. They started being "extra serious" and like 1+ hour episodes and it just was a drag to watch for me.

Go back and finish Deep Space Nine if you didn't watch it consistently, it's great and probably the most adult Trek. If you're looking for less of a commitment, Strange New Worlds is great. The only plot point you need to know going into it is

Discovery is pretty standalone but it's a very odd show. Everyone is very emotional and every episode is super dramatic. Not to everyone's taste but good if you want a Trek that reflects more modern TV.

Enterprise gets quite good as well, despite it's flaws.

Either Strange New Worlds (if you want new Trek) or go back and rewatch The Next Generation and Deep Space 9. Three best series IMO. The old ones hold up; SNW is up there with them.

Honestly I'd start back by watching TNG and then DS9 again. I assure you that you've forgotten a lot of it and you can experience it all again!

TNG, in my opinion. It's arguable about it being the best, but I think it's the fairest entry point. It was meant as a starting point in a way other shows were not.

First 2 seasons are bad, so I'd recommend an episode guide to skip past the offensive and bad.