Mayor Flaherty blames the Open Mic Night for the destruction of Farmer Dodge’s giant cucumber, prompting Holly and her friends to search for the real culprit.
Worried that Piper might beat her in the Pickle Pageant, Holly must decide between following other people's advice on how to win or being true to herself.
When her audition for the town musical doesn’t go the way she planned, Holly is determined to get a callback and prove that she’s meant for the lead part.
Mom forces the family to go on a camping trip without any electronic devices in order to spend quality time together – much to the chagrin of Robbie, Holly, Heather…and even Dad.
Holly’s excited to perform her new song at The Calico Cafe, but she discovers that Lyla and her cheerleaders are organizing a boycott against Open Mic.
At Nashville songwriting camp, Holly's perseverance is tested when she is challenged with creating an original song; Amy clashes with her co-CIT, Savannah.
Heather is dress coded for wearing a tank top and speaks up about the injustice on the internet. Lyla and Robbie argue over weighty real estate decisions, and Robbie makes a hasty purchase.
Holly feels a new sense of independence when she gets her driver’s license, but learns that with more independence comes even more responsibility. Heather finds herself excluded when she joins the boy’s football team.
Amy struggles to write her college essay. She decides to install wheelchair ramps around town for a better essay, but Holly and Savannah think the ramps are going overboard. Heather juggles dance and rugby and realizes that she can’t keep both.
Shortly after her breakup with Oscar, Holly discovers that he’s deleted all of their pictures online. She’s forced to work with him at the pickle festival and suspects he’s already dating again. Heather worries she’s becoming a third wheel.
Holly gets an audition at NYU, but is blind sighted with a music theory test that she’s unprepared for. Robbie is faced with a decision between his own gain and treating his employees right.
Amy’s anxiety grows when she watches a documentary about climate change. She realizes that it goes too far when she protests a BBQ fundraiser organized by her friends. Heather gets hurt during rugby and learns to prioritize her health.
Heather discovers that her school gives 90% of its sports funding towards boys’ teams and decides to take a stand. Holly finds a gig for her band, but Amy and Savannah aren’t as enthusiastic.
Holly finds that teaching music at the Children’s Club is more difficult than she thought. Heather rushes to build the crib for the new baby so she could join her friends at the movies.
Holly gets overwhelmed with post-grad plans and lets the stress interrupt her senior prom. Amy avoids going to prom to prepare for an important interview when she knows how much it means to Savannah.
With the loss of her dream job, Holly searches for her calling that will satisfy her passions in life. She’s conflicted when it comes to songwriting and philanthropy. The Hobbie family prepares for the new baby.