Theodore's Tough Tugging - Theodore and George are having trouble getting along, but sleepy Northumberland and ultra-loud Owan provide an example of working together by accepting each other's differences.
Theodore's Ocean Adventure - Rebecca is stuck in some icebergs and it's up to Theodore to use what he has learned from venturing into the ocean to save her.
Theodore's New Job - Theodore gets the new job of inspecting bell buoys, but soon begins acting a little too bossy. When he finally asks the bell buoys in a nice way to do what he wants, things get much easier for him.
Digby's Disaster - The other ships ignore disaster-prone Digby while working on a big project, but a slipped cable gives him the chance to show how useful he can be.
Dartmouth Says Goodbye - Dartmouth the Giant Cable Ship is ready to leave the harbour after laying the rest of his cables. Theodore however, doesn't want Dartmouth to leave, and has trouble saying goodbye to him.
Rebecca's Treasure - Theodore thinks that a day with Rebecca will be boring—but is pleasantly surprised when he finally gives it a chance.
Guysborough's Garbage - Canso Colossus helps the tugs and especially Guysborough appreciate how everyone contributes to make the Big Harbor a special place.
Theodore's Visit to Ceilidh's Cove - Theodore is sent to deliver a new propeller to a fishing trawler in Ceilidh's Cove. After finding the cove all by himself and giving Dorothy the Dory a ride out on the ocean, he finally knows how being bigger feels.
George's Turn - The tugs meet Sigrid, the new supply ship. While working with Sigrid, George becomes jealous and doesn't want to make friends with her. When George sees that he and Sigrid have a lot more in common, he changes his opinion, and they all become best friends.
Hank's Wheezy Whistle - Hank's whistle starts wheezing right before the Big Harbour Tugboat Races. When he doesn't get it fixed right away, it starts to get worse. In the end, Hank has his whistle cleaned and gets to start the tugboat race.
Northumberland is Missing - Theodore and Rebecca spend the day searching for Northumberland, who gets trapped on the bottom of the ocean after an underwater rock-slide bends his propeller. With the help of Shelburne, Northumberland is soon raised back to the surface.
Emily Goes Overboard - Emily is known for doing great turns in the Big Harbour, until she acts carelessly and gets herself stuck between two of the Pictou Peaks trying to do a turn right through them. Luckily, Digby the cable ship finds her and gets help from Theodore, who later pushes Emily out from the peaks.
Emily and the Splash - Emily, Sigrid, and Theodore can't agree on the best way to explore a sandy shore, so they decide to take turns.
Rebecca and the Big Snore - Benjamin Bridge keeps Rebecca up all night with his loud snoring. This makes her grumpy when she goes treasure hunting with Theodore and Shelburne. Both she and Theodore learn that nobody's perfect when Rebecca upsets everyone.
Theodore and the Lies - Theodore tells a lie to get out of dock duty so he can go racing with Hank, and a fire breaks out while he should have been standing watch.
Theodore's Bright Idea - Theodore makes the best of a bad situation when Lillie the Lighthouse is unable to warn an approaching ship because of her sore throat.
George and the Navy Ship - While trying to be just like his hero, Nautilus the Navy ship, George discovers that some things aren't as easy as they look.
Theodore's Prize - The tugboats have a contest for whoever does the best job each day, and the winner gets a prized flag. Theodore gets the job of hauling Bedford, but it's harder than he thought. In the end, Theodore doesn't get a prize, but something he gave himself.
The Dispatcher's Best Birthday - The tugs wanted to surprise The Dispatcher for his birthday. But due to some troubles on the sea, the tugs we're upset that they used up all their time for the party. The Dispatcher was pleased of how hard they worked for the day and that was a present enough.
Emily's Easy Job - Theodore thinks he will never do a good job of tugging ships in like Emily, but soon realizes that the things he can do are important.