There’s a small side-path through the grass to the right of Molly, where you can find a Poke Ball (Useful!), and otherwise the grass here is the same as the grass by the entrance of the ranch.  Now that you’ve got that done, head back and up the path you didn’t go along before.  Hugh catches up to you for a moment, wonders if Herdier wandered off into ‘the back’, and then rushes ahead, telling you to come along.  He stops just up the stairs, next to some more grass.

When you cross the grass (again, just the same as the grass by the entrance) and near the next stairway, he rushes to catch up, and then offers to share something with you- a Paralyz Heal he’s found.  He then points out that Pokemon usually don’t wander off on their own, and if things are really bad, it might be involved in ‘some trouble’.  This is pretty vague, but then Hugh does seem like a rather vague sort of a person.  He stops there, looking around- and this gives you a chance to face the old man who’s lingering back here.

Battle: Janitor Orville (98 Poke)
Opponent: Lillipup Lv 6, Mareep Lv 6

From here, head down the stairs.  Yet more grass, still of the same content, is here, along paths leading both right and downwards.  The downward path just leads over a ledge back to where you came from, so head to the right.  There’s a trainer nearby within sight, so go ahead and handle him next.

Battle: Youngster Kenny (96 Poke)
Opponent: Patrat Lv 6, Psyduck Lv 6

Heading down from where Kenny is yields an X Attack, a not-terribly-useful battle item.  Head back up and through the backmost path behind Kenny’s little clearing, going on to the right.  You’ll hear a barking, at which point Hugh catches up to you again.  He asks if you heard that, then says he’ll look around this area and you should head further into the grove.  Downward from Hugh you can find another item ball, which holds another Potion.  You can also see someone in a black hat doing something with a Herdier- a bit alarming.  Continue downwards until you reach the spot where the walkable path splits- you want the split on the right.  This will let you hook around some trees and approach the Herdier and the strange person.