Worf's foster brother, Nikolai Rozhenko (Paul Sorvino), is a cultural observer stationed on the planet of the Boraalans, which is in the process of undergoing sudden atmospheric dissipation. This will result in the immediate deaths of the world's pre-industrial population, but Picard can't evacuate any of the Boraalans because that would violate the Prime Directive. But Nikolai, who has "gone native" and is determined to save a fraction of the Boraalan society, secretly transports a village of people into the holodeck while they're sleeping, with the plan of keeping them there until the Enterprise can find another planet for them to live on. If they can pull off this plan, the Boraalans would be none the wiser.
"Homeward" is a frankly tiresome examination of the Prime Directive that makes all parties involved look like pawns in a philosophical construct rather than human beings exercising choices over other human beings. By the end, we have a muddle of themes and inconsistent points of view rather than any sort of useful examination of the Prime Directive's virtues. When Picard has to sit idly while watching an entire society be destroyed, you can't help but wonder where the nobility is in this sort of non-interference. I also find Picard's reaction to Nikolai's solution, once he's found out, to be overstated. Picard is strongly disapproving of what Nikolai has done, and then has to be dragged practically kicking and screaming into being a part of the solution once it's been laid out. I couldn't help but think: Hey, you're the captain. You could always beam them into space if you feel that strongly about leaving them to the fate of the Prime Directive. Same net effect.
Worf is assigned to help Nikolai guide the Boraalans through the tunnels in the holodeck simulation so they can experience the illusion of journeying to their new home. This is all the better to encourage banal dialogue of sibling disagreements allegedly going back decades but mostly feeling completely invented for right now, considering we've never heard of Nikolai before. The opposing forces of Worf's rigid responsibility versus Nikolai's chaotic spontaneity makes for some dull scenes.
And I've had enough of vague primitive village societies seen through the boring lens of supposed anthropological study. These villagers (which include such spinoff Trek guest stars as Penny Johnson and Brian Markinson) are phoned in as story subjects. Meanwhile, we have all the predictable mechanics involving the holodeck, which, of course, is malfunctioning (introducing a needless problem in need of a solution), so all the malfunctions are explained to the villagers as "omens" and so forth. It's just tedious.
Inevitably, one of the villagers gets out of the holodeck, compounding the problem. At this point I was wondering, why isn't the damn door locked? Why doesn't someone just knock the guy out with a hypospray so he thinks it was all a dream? (For that matter, why not just put the whole village to sleep for the duration of the journey instead of using the holodeck at all?) Instead, people tell him exactly where he is and explain everything and make things worse. Then Crusher says she can't wipe the guy's memory. (Glad we're considering extreme options after having not thought of simple ones first.) Ultimately, the guy kills himself rather than go back to his villagers with knowledge about space and starships and stuff. Picard regretfully muses how he'd hoped maybe this guy could bridge the gap between the Federation and the Boraalans. And I'm thinking: Huh? A few days ago you wanted to wash your hands of this holodeck plan, and now you're willing to contaminate the entire village for an experimental first contact?
And so on. "Homeward" is an unfocused, ponderous, implausible, too-clever-by-half exercise in Prime Directive holodeck tedium, with a needless layer of season seven Family Tree Theater thrown in for no good reason. I wasn't a big fan of "Who Watches the Watchers," but it's a much better examination of the Prime Directive than this.