Mark Hope
Hero
For BX, I would go with Lost City over KotB. It's a great dungeon with a cool premise and has more weird atmosphere than the Caves of Chaos. Alternatively, send them to the Isle of Dread and have them be brain-fried by kopru in a volcano.As a 50th anniversary celebration I'm planning a tour across past D&D editions with my players. I want to run a short-ish module for each edition, preferably a "classic" one like Keep on the Borderlands, using just the core rulebooks. The candidates are:
OD&D: honestly, I'm skipping this one since it's really hard to run it without a retroclone, and I think using a retroclone that makes the rules coherent would defeat the purpose of playing OD&D. If someone have another idea I would be glad to know.
D&D B/X: B2 The Keep on the Borderlands. I think it perfectly encapsulates the pitch of a classic short-ish adventure to showcase the edition.
AD&D 1e: T1 The Village of Hommlet or U1 The Sinister Secret of Saltmarsh, both really good low level modules. I'm more inclined to U1, even though T1 is the most remembered one.
AD&D 2e: I don't know yet, but I want something to showcase where 2e era was different from 1e. Maybe something with Planescape or Spelljammer.
D&D 3.X: Maybe Red Hand of Doom, but I think it's too long for the premise of this tour.
D&D 4e: I really don't know, I never played 4th edition but I'm curious to give it a shot without judgements.
D&D 5e: Lost Mine of Phandelver, of course.
For AD&D, absolutely Saltmarsh over Hommlet. U1 is one of the greatest adventures of all time.
For AD&D2e, consider Curse of the Azure Bonds. It's railroady as hell and basically takes the PCs from one awesome set-piece to another. Battle a beholder in Zhentil Keep. Fight the corpse of a dead god. Infiltrate a thief guild's sewer hideout. Face the BBEG in the ruins of Myth Drannor. I love this adventure and if your players buy into the concept, they're in for a great ride.