Currently Milliways' Wilson is working his way through Adventure Mode, the story mode campaign of the original game, which is accessed by finding a portal (Maxwell's Door) in Sandbox Mode. This version of Wilson is based very heavily on a real savefile of mine in which I first completed Adventure Mode, although I'm consolidating it with some other Sandbox Mode saves in order for him to know about things like Sandbox Mode world-jumping and the Ruins which I didn't touch in that specific save, not to mention that I didn't have the Reign of Giants expansion pack at the time but I've used its features here.
Come Sail Away's Wilson comes in from the exact instant he saw a piece of the moon fall out of the sky and was about to get hit by the ensuing tidal wave in the Turn of Tides trailer that began Return of Them. He's been to Shipwrecked and Hamlet (before undergoing the same Adventure Mode run as the Milliways version did) but not the Forge and Gorge.
So, his timeline looks like this; some spoilers for the first game below.
Nobody in the fandom knows whether the other DST characters can follow their friends into the Forge portal or where Wolfgang, Willow, and Wigfrid went when the others entered the Gorge.
Milliways: If we get more Don't Starve characters in the Bar who weren't in the Forge/Gorge trailers, they can be substituted whenever we get to playing through those events rather than saying they followed the canon teams; it'd be simpler and probably more fun to RP out a Forge or Gorge OOM together. Wilson might go to the Shipwrecked or Hamlet worlds eventually! But probably through some kind of Bar shenanigans in the DST era, (for instance, the portal in the lake) rather than building the Seaworthy or Skyworthy in his original Sandbox Mode world.
Come Sail Away's Wilson comes in from the exact instant he saw a piece of the moon fall out of the sky and was about to get hit by the ensuing tidal wave in the Turn of Tides trailer that began Return of Them. He's been to Shipwrecked and Hamlet (before undergoing the same Adventure Mode run as the Milliways version did) but not the Forge and Gorge.
So, his timeline looks like this; some spoilers for the first game below.
- Pre-canon: Flashback portion of the Interference cinematic, Origins trailer (Forbidden Knowledge), various millicanon before that. Wilson leaves the university he was doing his graduate studies at in disgrace, and after an unspecified period of time he buys a furnished home at auction which turns out to be in worse shape than advertised and full of what turns out to be Wagstaff's old stuff. A strange voice talks to Wilson through his radio, he rather hastily agrees to receive forbidden knowledge from it, he spends weeks obsessed with building some elaborate contraption unaware of what it does and then when he activates it (at Maxwell's urging) it sucks him into another dimension.
- Sandbox Mode: Wilson arrives in the Constant, not that he knows that name for the island dimension at this point. First face-to-face encounter with Maxwell, first experiences with temporary death and revival starting with touchstones and later with resurrection items he crafts himself. Tries to use the Sandbox Mode teleportato to leave, but ends up on a different version of basically the same island (same climate, same species of creatures, same phenomena, but laid out differently). Milliwaysverse hasn't been to Shipwrecked or Hamlet, Sailsverse has been to both.
- Adventure Mode: Wilson activates Maxwell's Door and travels through a series of challenge worlds. There are six of them but players will only see five at a time, in a variable order; they're generated anew for each attempt, but each challenge world has specific constraints applied to it and otherwise resembles a somewhat harsher version of the Sandbox Mode island. The goal is to use the Divining Rod to locate the components of the Teleportato, assemble it, and escape to the next world. Wilson made seven unsuccessful attempts to get through Adventure Mode before his current one, by which I mean he died without a resurrection arrangement in place and found himself back at the portal in Sandbox Mode.
- World 1: The King of Winter. The island's biomes are broken apart and connected by narrow land bridges with obstacles in the middle, but more importantly it's always deep winter. It's too cold to grow crops, daylight hours are very short, and irritable Deerclopses roam the countryside ready to stomp on your camp if they notice it. (If you kill it, another one will be along in a few weeks.) Wilson owes much of his survival here to looting some winter gear from the skeletal corpse of some other adventurer who died mere steps away from the Divining Rod base. This is also the world where he got his hat and walrus-tusk walking cane since there's MacTusk hunting parties all over the place.
- World 2: The Game is Afoot. Still winter for the first ten days, then the weather warms up and stays that way forever. The island layout puts a hospitable area in the middle and three dangerous peninsulas which of course contain all the Teleportato parts and a lot of desirable resources. Most notable as the place where a lureplant sprouted in the middle of Wilson's camp while he was scouting and ate everything he left lying on the ground, and as the site of Spiders Gorge, Land of 1000 Spiders, all of which were usually busy fighting tallbirds.
- World 3: Two Worlds. Two islands, one hospitable and one intensely inhospitable, with warm-but-not-scorching weather and no harsh seasons; autumn and spring sort of mush together without passing through a distinct summer or winter. Wilson is deposited on the hospitable island in a small, easily-expandable prebuilt camp with gardens and a tent while Maxwell bargains with him, and there's a diseased wormhole on the nice island that's clearly supposed to be a one-way trip to the bad island. However, wormholes really love burrowing between disconnected bits of land and providing passage between them so there's a second healthier wormhole on the opposite end of the hospitable island anyway. Wilson used that to scout the inhospitable island and discovered that it's mostly swamp and full of deadly tentacles and hostile clockwork robots and killer beehives and stabby booby-traps and so forth. The far end of the wormhole came out near some hound dens and Wilson had to fight the hounds off and then smash the dens the first time he used it. Also this wormhole keeps spitting him out at Milliways instead, regardless of whether he's coming or going; that's how he first came to the bar.
- World 4: Archipelago. ◄ You Are Here (Milliways)
This world has normal seasons and is broken into six islands which are each dominated by a single biome, and all but the starting island contain a piece of the Teleportato. Wormholes connect them all to each other, most going through a 'hub' island which also has the base of the Teleportato on it. Unfortunately in this case the hub island is filled with killer bees. Wilson tried to burn the hives and started one hell of a forest fire but did not successfully get rid of all of them. The good(?) news is, wormholes provide access to Milliways! - World 5: Darkness. No wormholes here, unfortunately. Perpetually early autumn, but also perpetual night. Similar partially-broken-apart layout to King of Winter. A lot more fireflies than the island typically has, including in biomes where they usually don't live. Maxwell screams at you when you spawn in. Wilson ends up spending a lot more time than would generally be considered necessary in this world due to some questionable strategic choices he makes, but he eventually finds the exit.
- Checkmate: Epilogue. Wilson finds Maxwell's throne room and takes his place on the Nightmare Throne. Maxwell apparently dies and crumbles to dust upon being released from the Throne, but in-game he becomes the player character in your Sandbox Mode world.
- Cyclum: An official comic (with a cinematic embedded in it) that bridges the events of Don't Starve and Don't Starve Together. Maxwell fumbles his way through being a survivor on the island he used to reign over and finds Wilson's camp, with Wilson in it. Wilson's immediate reaction is trying to beat the snot out of Maxwell with his bare hands, and they have a brief scuffle interrupted by a shadow hand that wants to snuff out the campfire and likely get both of them killed by the monster in the darkness. Both of them immediately stop pummelling each other and rush to throw another log into the fire, and then they're too exhausted to fight any more so they sulk for the entire next day.
Eventually Wilson's resolve cracks and he trades Maxwell a kebab for information about why the hell he isn't dead; Maxwell has no clue and counters by asking Wilson why he's not trapped on the Nightmare Throne. Wilson tells Maxwell about how a woman walked out of the darkness, released him from the Throne with a tap on his bonds, and then horribly murdered him with magic. The A New Reign trailer explains what happened after that. The two of them have an informal truce after that but once again come into conflict when Wilson finds Maxwell rummaging through his chests and looking at an old blueprint; Maxwell smooths over the situation by offering to improve the plans with magic from his Codex Umbra, and the two of them work together to build a new portal (which looks like the spawn portal from when Don't Starve Together was in beta, incidentally). Despite some discomfort with the situation Wilson is the one to throw the switch, at which point the portal activates. It very much does not do what it was supposed to do; instead it immediately summons three other survivors and then collapses, torn apart by enormous thorny rose-vines, and a fancier but broadly similar portal rises out of the ground in its place while the new people (Wes, Wendy, and Wolfgang) look around apprehensively. - Don't Starve Together: Survival Mode is very much like the first game's Sandbox Mode, there's just more of you. Other survivors were pulled from their own singleplayer islands to the multiplayer world, potentially including anyone who appears in the singleplayer game but definitely everyone who's present in an unmodded copy of DST. (Wortox is an exception to this; he's basically an interdimensional tourist, he wasn't stranded on the island in the first game but he can show up whenever he wants.) Not everyone finds the five-person band of survivors formed after the original portal incident right away, some come through the portal alone and band together in twos and threes before meeting the rest. Eventually, though, they all come together into one community. Things start to change in the island ecosystem, new plants and animals and creatures that blur the two kingdoms appear, the island starts getting hit with meteorites on a regular basis, and the first person to venture underground discovers that the upper level of the caves has collapsed onto the sub-subterranean ancient ruins and there's no longer a hard barrier between the two. At some point Maxwell or Ms. Wickerbottom introduces the name 'The Constant' for the island dimension, based on its stability compared to some of the other realms it connects to.
- Return of Them: ◄ You Are Here (Come Sail Away)
One night a piece of the Constant's moon falls from the sky and crashes into the ocean, flooding the area around the island with several feet of real saltwater from some punctured underground reservoir where previously there was only weird impassable two-dimensional mock-waves. Various seabirds and fish colonise the new waters, not all of them friendly; the island itself is almost entirely unaffected as it was previously several feet above sea level at every accessible point of the shoreline. Wilson is the first to suggest building boats to investigate the crash site and the first to build the new science machine specialising in nautical items, the Think Tank. - The Forge: Eventually, either because they want to see what happens or because they've run out of other things to do, the survivors team up to kill the Ancient Guardian and the Ancient Fuelweaver down in the ruins. (These figures are also not subject to permanent death in the Constant, incidentally; they respawn after a while when certain conditions are met.) Wickerbottom sockets the Ancient Key into the Ancient Gateway, which generates a portal, and Wigfrid barrels headlong into it shouting for glory while the other five people present at the time are still trying to decide what to do with it; Wilson, Willow, Wickerbottom, Wendy, and Wolfgang get pulled in after her and find themselves in a gladiatorial arena surrounded by warrior-pig spectators and lava. Their leader, a human man named Battlemaster Pugna, refuses to believe they're not footsoldiers of the forces controlling the Nightmare Throne and forces them to fight all the warriors he can throw at them; after they accomplish this, he surrenders and opens the next portal for them.
- The Gorge: Half of the team who fought in the Forge - Wilson, Wickerbottom, and Wendy - emerge in a dilapidated quasi-Victorian town which is always overcast but never night and has a giant fanged lamprey-like mouth in the sky like a wormhole gone horribly wrong. Its name is the Gnaw. What remains of the local population is a group of goat-people and pig-people who have been cooking meals to placate the Gnaw, and a few of the fish-people who failed to please the Gnaw and fell victim to its curse of transformation but didn't die, go mad, and/or disappear into the sea. Upon the survivors' arrival the Gnaw refuses to accept any further meals from the locals; the humans are the only ones allowed to cook for it now, and the curse will get them too if they don't measure up. If they lose, they turn into merms; if they win, they get to go through yet another portal, destination unknown, with the population of the Quagmire following behind them. By the way, the Quagmire has a park gate, so access to Milliways is possible here.
Nobody in the fandom knows whether the other DST characters can follow their friends into the Forge portal or where Wolfgang, Willow, and Wigfrid went when the others entered the Gorge.
Milliways: If we get more Don't Starve characters in the Bar who weren't in the Forge/Gorge trailers, they can be substituted whenever we get to playing through those events rather than saying they followed the canon teams; it'd be simpler and probably more fun to RP out a Forge or Gorge OOM together. Wilson might go to the Shipwrecked or Hamlet worlds eventually! But probably through some kind of Bar shenanigans in the DST era, (for instance, the portal in the lake) rather than building the Seaworthy or Skyworthy in his original Sandbox Mode world.