Overhearing Blueberry reading a story to the baby Berrykins about the scary Galumphalot, Orange is uncharacteristically shaken. She determines she doesn't want anything scary around her, just relaxation. But while the girls are having a hair-styling party at Lemon's salon, a malfunction at the BerryWorks causes the whole town to go dark. And Orange begins to get really anxious.
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With the summer almost over, Blueberry overhears Strawberry talking about a wonderful tropical island and believes her friend is going to surprise them all with a much needed vacation! Blueberry makes the other girls promise to keep the secret until Strawberry reveals the big surprise. Of course, even though they've promised to keep the secret, they can't help but try and suss out what the island's like from every little thing Strawberry does.
Berry Bitty City is holding its first city-wide talent show! Hearing that it's the music students of superstar Cherry Jam, a talent scout from Big Bitty City plans to show up. Strawberry and her friends excitedly anticipate her arrival.
Cherry Jam is so enjoying staying in Berry Bitty City, that she calls her managers in Big Bitty City and informs them that she is going to stay for a much needed vacation! Strawberry and the girls are thrilled that she will be with them for a little longer, and they do all they can to make their guest comfortable. But Cherry doesn't want to be treated like a guest she wants to fit in and contribute to the community.
With time running out before the Grand Opening celebration for the new Marketplace, Strawberry's friends get the idea to invite her favorite singer, superstar CHERRY JAM, to be the guest singer. The girls are blown away when their berryjuice cell phone gets a text message that Cherry accepts their invitation! Strawberry is touched by their surprise, but reminds them that now the town and Marketplace really have to shine!
Strawberry is really touched when her girlfriends and the Berrykins volunteer to help her with the construction of her new marketplace, so when the girls suggest they take charge of designing Strawberry's dream-bedroom to go on the second story, of course Strawberry agrees. While construction is going on, the girls each show Strawberry their individual ideas for the bedroom.
Finding she has some free time one morning, Strawberry visits Berrykin Bloom who is filled with excitement over his new crop of Berry Bitty fruits and vegetables his garden has never grown so much produce! He can't wait to share his new crop (the perfect bitty size) with Berry Bitty City, so Strawberry volunteers to help him transport the produce to Orange's General Store.
After returning to the café after a walk with her pets, Strawberry is met by Mr. Longface. He's been waiting for her so that they can get started making treats and decorating for Sadiebug's and Kadiebug's party that afternoon. But Custard and Pupcake have enjoyed their time outside so much that they want to continue playing.
While working in her store, Orange overhears the Berrykins laughing and shouting outside. When she goes to the door to investigate, a clump of dandelion fluff gets blown inside chased by three Berrykins. She watches as they head butt the clump around until it floats back toward Orange. Just as it floats close, she gives it a bat sending it outside and the Berrykins happily chasing after it. Wanting in on the fun, she joins them.
Lemon is ecstatic. She races out of her salon and goes around to the other girls' houses proclaiming that she "did it!" and beckoning them to join her. They follow her back and are completely dazzled by her newest creation - Glamicures. They are brightly colored, jeweled manicures with tiny microchips inside that play songs when the wearer moves her hand. Each girl lines up to receive her new glamicure and soon there is a cacophony of color and sound.
While sipping cider in Strawberry's café, the girls muse about how they cannot wait for winter to arrive. They list the various traditions they love about the season but the one they all agree on is the Glimmerberry Ball. Strawberry mentions that she doesn't think the café can hold the party this year because of how the town has grown. The girls decide to split up and search for a new location.
Raspberry is distraught when she suspects her friends have copied her design on her lantern for the "Glimmerberry Gathering".
The girls are all gathered at the café. Strawberry is experimenting making applesauce from scratch with a mallet (and making a mess) while the rest busily make their own wrapping paper and bows for the annual gift exchange they hold in celebration of First Frost. Mr. Longface stops by and Strawberry offers him some fresh applesauce but he declines, as he doesn't care for it. He's only there for some tea and, being that he's new in town, doesn't know what the group is up to.
Friends from all over the world descend on Strawberryland to take part in the first Great Friendship Festival. Strawberry thinks the festival will provide a wonderful opportunity to see the world through different eyes.
Strawberry Shortcake travels to magical Holidayland with Honey Pie Pony, searching for the perfect presents to give her friends. A trip to the North Pole and a visit with Santa make this adventure truly wonderful, until a pile of melting snowballs turns Strawberry's carefully selected presents into a soggy mess. It all ends well, though, when Strawberry's friends remind her that the best gift of all is the gift of friendship.
When a storm causes a giant boulder to cut off Berry Bitty City's water supply, Strawberry and the girls face the possibility of having to move away from their homes. With the help of Mr. Longface Caterpillar, the girls set out on an adventure to save their town.
While sipping cider in Strawberry's café, the girls muse about how they cannot wait for winter to arrive. They list the various traditions they love about the season but the one they all agree on is the Glimmerberry Ball. Strawberry mentions that she doesn't think the café can hold the party this year because of how the town has grown. The girls decide to split up and search for a new location.
It appears winter is finally coming to an end and Raspberry is planning a big fashion show to display her spring line. Her vision is to have the girls model her fashions in a parade past the town fountain. What she didn't realize is that the Berrykins are turning the fountain into a big water show. Every time the girls come to rehearse, they must comically dodge jets of fruit juice from the out-of-control fountain-the Berrykins are still working out the bugs.
Out gathering berries one day, Strawberry & her pets find a tiny fairy among the berry vines. Realizing that Strawberry is a very kind & caring person, the little fairy decides to take advantage of the kid's good nature.
"When the East Wind blows, it means your berry favorite dream will come true," or that's what Strawberry Shortcake's always heard and she believes it. Strawberry dreams of a world where she and her friends can grow better everyday. But when a poor berry crop puts a strain on the Strawberryland resources, it puts a strain on Strawberry's friends, too. And when the strain causes a falling-out among them, it's a nightmare for Strawberry Shortcake.
Raspberry is distraught when she suspects her friends have copied her design on her lantern for the "Glimmerberry Gathering".
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