D&D General A gaming tour through the editions of D&D

Hriston

Dungeon Master of Middle-earth
I’d be tempted to run a 20-level campaign premised on the PCs becoming slightly different versions of themselves as they move to each new “world” (edition). This is how I’d divide things up:

OD&D - levels 1-4. I think The Keep on the Borderlands would be good for this, maybe throwing in "Tower of Zenopus" from Holmes Basic and/or In Search of the Unknown. The wider setting, if it enters into actual gameplay, would be as described in KotB which looks like the setting of Three Hearts and Three Lions with the “Realm” of Law to the west and lands of Chaos to the east. Caverns of Thracia also sounds good to use here but recommended character levels might be too high to fit in along with B2. Once 4th level is reached, the "Cave of the Unknown" could contain a portal to Greyhawk...

AD&D 1E - levels 4-7. Greyhawk (folio/boxed set). I think Temple of Elemental Evil (T1-4) might slot in well here, but (edit: after consideration, T1-4 appears to have too much content to get through in the desired range of levels, but see 3E below) it might be better to string together 1) Dwellers of the Forbidden City, 2) The Hidden Shrine of Tamoachan, and 3) White Plume Mountain, in that order. The Aerie of the Slave Lords (A1-4) could also work here.

AD&D 2E - levels 7-10. Greyhawk (From the Ashes)/Planescape/"The Shirelands". I might use Fate of Istus to transition the characters to 2E. Then, I'd run 1) The Gates of Firestorm Peak, 2) Dead Gods, and 3) The City of Skulls.

3E - levels 11-14. Greyhawk (The Adventure Begins). Return to the Temple of Elemental Evil could, I think, be done within this level range.

4E - levels 21-25. Nentir Vale. 1) Death's Reach and 2) Kingdom of the Ghouls.

5E - levels 17-20. The Multiverse (Forgotten Realms). The only published 5E adventure for tier four is Waterdeep: Dungeon of the Mad Mage, so it's an easy choice. I suppose a conversion of 4E's Prince of Undeath would work well here too, to complete the epic tier trilogy.

ETA: I’m really liking this idea and am going to continue adding to this post as I flesh out the details.
Update: I started with @Reynard's idea of using the settings that best exemplify each edition, but the focus changed to hitting the "greatest" published adventures, mostly influenced by the "30 greatest adventures of all time" list.
 
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Voadam

Legend
I ran a Pathfinder game where when the PCs went into the fey First World which is a more primal reality with arcane rules that are both obscure and intricate, I ran them in 1e rules while there, which was temporary.

A plot to go through different editions in different planes of reality could be fun. Is by the book 1e Lawful Evil Hell?

Generations of heroes where the world keeps changing as time goes on so one edition per generation could be fun.

The same heroes multiplied into different editions could be a neat reincarnation or eternal champion theme campaign too.
 

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