Hurdle Hill first appeared in the episode "The Pirate Pup!",Jake and his crew are searching for their pirate puppy friend, Patch, who has sunk aboard the Jolly Roger and stole Captain Hook's boot. Patch flees from Hook's ship onto Shipwreck Beach, hiding in the various wrecks to evade being captured by Hook and his crew Jake and his crew distract Hook and his crew by barking to allow Patch to flee into Hurdle Hill. Izzy informs the viewers to guide Patch safety into the right path leading to Butterfly Bluff. Hook and his crew soon end up in the fork in the road, Smee suggest they follow down the right path as the young pirates said, but Hook refuses to listen to both Smee's and the puny pirates words and orders his crew follow him down the left path sending the Jolly Roger crew plummeting into the muck of Stinkpot Swamp.