- Theodore's Whistle - Embarrassed when a visiting ship calls his whistle "cute," Theodore tries so hard to sound like the other boats that soon he can't whistle at all. Queen Stephanie helps him learn to appreciate his own unique sound.
- George's Ghost - George loudly tells everyone he doesn't believe in ghosts—then spots what he thinks is a ghost ship.
- Theodore Changes Sides - George's invitation to sleep over on the side of the dock with the ocean-going tugs has Theodore feeling a little too important for his old friends.
- Night Shift - Theodore and Hank volunteer for the night shift and discover how different—and scary—things can look in the dark.
- Whale of a Tug - A young whale named Walter wanders into the Big Harbour, and he and the tugs learn a lot about each others' lives.
- The Tugboat Pledge - Emily is chosen to create a "Tugboat Pledge" and learns the importance of taking others' needs and feelings into account.
- Emergency - George meets a ship who can't talk and wishes he'd paid more attention to his signal-flag lessons.
- The Cold Snap - When he must choose between following orders and helping a ship in need, Theodore learns that even the Dispatcher makes mistakes.
- Hank and the Hug - The tugs are not having much luck raising Hank's sinking spirits, until Theodore realizes that what Hank needs is a gentle "tug hug."
- Emily and the Rocket - Emily goes looking for a sunken rocket ship with Constance the Coast Guard.
- Foduck Stays Home - While serving as official safety tug, Foduck prevents an accident and learns why it's so important for the safety boat to stay in the Big Harbour.
- Theodore the Tug in Charge - After Theodore tugs back the wrong ship and starts to lose faith in himself, Bedford Buoy helps him regain his self-confidence.
- Theodore in the Middle - An argument between Emily and George leaves Theodore feeling torn between his two friends.
- Carla the Cool Cabin Cruiser - Emily must choose between following the rules and being "in" with Carla the Cool Cabin Cruiser.
- Snorri the Viking Ship - Everyone is a little afraid of the new arrival, but Theodore convinces them to look past their fear and make a new friend.
- Tug of the Year - George loses the Tug of the Year contest, but discovers that he can still be a winner by taking pride in everything he does.
- Theodore the Jokester - Theodore loves telling jokes about Rebecca the Research Vessel. But when the tables are turned and someone starts telling jokes about him, he learns how words can hurt.
- Emily the Vigorous - Emily has to figure out how to get all her work done and still have time to meet a visiting fishing trawler.
- Theodore's Day Off: Theodore makes up an excuse to play hooky for a day, then feels sorry about the deception.
- Foduck and the Rainbow - A rainbow helps Foduck see that sometimes the unexpected can be wonderful.
- Benjamin Bridge
- Phillip and Filmore
- The Dispatcher
- Queen Stephanie
- Donald Dock
- Gloria Cornwallis (does not speak)
- Chimey (cameo)
- The Flat Eyed Coast Guard Ship (cameo)
- Margaret (not named)
- The Broken Bell Buoys (do not speak)
- Caroline (not named, does not speak)
- Beiderbeck (mentioned)
- This is the first season to have new models for the tugboats.
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