29 – Route 28 to Route 39
Head out the western exit of Ecruteak City. It is time to start pressing toward Olivine, the next badge and the sick Amphoros await. Head westward from the exit of Ecruteak and you will see the path split by a fence.
Above the fence:
If you stay above the grass, you will be challenged by Sailer Harry. He will lead with a Wooper lvl. 20. It will likely attack with Slam, Mud Bomb or Mud Shot. Nothing too big about this battle.
Again, you can dodge the grass and keep to the higher stretch of this area to encounter another trainer. This is Lass Dana. She will lead with a Flaaffy lvl. 19. It will likely start with Thunder Wave to Paralyze your Pokemon then attack with Thundershock. After that Pokemon faints she will follow it with Psydfuck lvl. 19. It will likely start with Disable, trying to take out your last used attack. After that, it will come at you with Confusion. After the battle, Dana will offer you her number so when she gets some items she can share them with you.
If you follow the path above the trees and grass from Dana you will encounter School Kid Chad. He will start with Mr. Mime at lvl. 20. It will likely start with Mimic and learn the attack you recently used on it. After that, it may use Meditate to boost its Attack then come at your Pokemon with the attack it learned from yours or Doubleslap. After you beat him, he will offer you his number so he can talk to you about Professor Oak.
If you walk in the grass below Chad, you will see another trainer. This is Beauty Valerie. She will lead with a Hoppip lvl. 18. It will likely come at you with Tackle, though it is not very strong, akin to a Magikarp. It may also try to use Poison Powder, Stun Spore or Sleep Powder on your Pokemon. After that she will send in Skiploom lvl. 18. It has Tail Whip, so it will likely try to reduce your defense then attack with Tackle.
If you go below the fence:
This leads you down a path. If you go left, staying above the second fence, which has a break you can head south through, you will encounter Bird Keeper Toby. He will lead with a Doduo lvl. 16. It will play aggressive and likely come at you with Quick Attack, Rage or Fury Attack. After that he will send in either Doduo lvl. 17 or 18. The one at lvl. 17 or 18 will behave much the same as they all have the same move pool.
After you beat Toby, take a moment to loop around the fence to grab the White Apricorn that is on the tree behind him. After that, head back and hop over the ledge to grab the item ball that is nearby that has a Max Potion inside it. After that, head to the left, into the grass. There you will encounter Bueaty Valerie. She will lead with a Hoppip lvl. 18. It will likely come at you with Tackle, though it is not very strong, akin to a Magikarp. It may also try to use Poison Powder, Stun Spore or Sleep Powder on your Pokemon. After that she will send in Skiploom lvl. 18. It has Tail Whip, so it will likely try to reduce your defense then attack with Tackle (Please note this is listed for completion, hence the repetition here). After that, head to the left, up the stairs, to reach Route 39