As Abigail shows Phil the sights of Middleton, they stop in Cassie’s shop and run into Martha, who is in need of advice. She is looking for someone to update the Middleton website to include recent town history. Cassie recommends Martha approach Grace to do the job.
Later that evening Cassie gets a call from Sam, who is in the hospital getting checked out for a muscle strain. Cassie says she will be right over. She finds Liam with Sam, who tried to fix a shingle on Liam’s roof and ended up falling and hitting three baby pine trees on the way down.
Abigail and Phil grab some coffee and go for a stroll through the park. He wants to know more about what made Abigail settle in Middleton after living in New York. He also alludes to the fact he has done some background research on the internet about Abigail. Abigail smiles and says she has done her own research on him too.
Cassie takes Sam home and makes sure the house is all set up for him to just rest. Sam brings up the fact that Cassie was concerned about the wedding when she found out about Sam’s injury; he wants to talk about the upcoming nuptials. However, she is still not ready to discuss the specific details of the big event.
Back at City Hall, Grace and Martha’s assistant Jared go through old Middleton archives. Grace becomes more and more fascinated with the old photos she is finding and Jared tells her she has all-access to the photos. Grace comes across an old photo of Martha’s great-grandfather at a Chicago Cubs game on opening day. But if that photo is real, it means he didn’t really save a family from a burning building on the same date, an act for which he was famous. Martha is shocked to learn that the legend about her family name isn’t true.
Sam gets an urgent call from the aid organization he worked with in South America and now they need his medical help in Colombia. He immediately books a flight and places a call to Cassie to fill her in. The next morning Cassie puts together a care package for Sam to take to Colombia, which includes a pen light and scarf. Eve fills Cassie in on the reasoning why the organization needs Sam so badly, citing the recent storms the country has experienced. Suddenly, Cassie becomes concerned over Sam’s trip. Back at Grey House, she gives Sam the care package items. Sam promises Cassie he will be safe and tells her he loves her.
Back at Grey House, Abigail tells Cassie that she has been showing Phil all around Grey House. Cassie suggests taking him to the Old Mill, especially since it recently snowed up there. Grace shows up and tells her mom about the updates she has been giving the website. Grace also fills Cassie in that Martha’s great-grandfather’s heroic story was based on a lie. Cassie gives Grace a map to where the fire originally took place, now occupied by a park, but the street corner is still named after the Endicott family.
Cassie corners Nick and asks how his college applications are going. Nick says he has yet to really even apply, yet because he has no idea what he wants to do. Cassie assures Nick that he doesn’t have to have every detail of his future figured out, no matter what his friends think.
When Sam arrives in Colombia, he sees firsthand how the storms have affected the country. He is immediately put to work on patients suffering from injuries. In the medical tent, Sam examines a baby and realizes he doesn’t have enough light. He uses Cassie’s pen light, which helps him find the obstruction in the infant’s ear.
Abigail takes Phil to the Old Mill and shares the story of how it is haunted by a woman who died of a broken heart. Phil hangs on her every word. He asks Abigail if there are any stories of a man and woman at Old Mill sharing in a kiss. Abigail says she doesn’t think so and Phil slowly moves in and kisses her on the lips.
While at the bistro for dinner, Cassie notices how busy Stephanie is. She says she is short a delivery person and Nick offers to help out. Cassie and Grace point out that Nick is just putting off his college applications and he doesn’t deny it. As Grace is about to leave to go back to City Hall, she finds an extra-bubbly Abigail and takes note of the change. Abigail pulls up a seat next to Cassie and notices that her cousin is in a glum mood. Cassie says she can’t shake the feeling of worry over Sam being in Colombia. She hasn’t had that feeling since her first husband Jake would leave for the job and she would never know if he was coming back.
In Colombia, Sam continues to work hard getting treatment to patients in the medical tents. He notices one man with a sore arm. When Sam asks the man’s daughter how long her father’s arm has been hurting, she acts as translator for Sam. Sam notes that the man needs a sling for a sprained shoulder and uses the scarf that Cassie gave him to get the job done.
Back in the basement of City Hall, Grace helps Jared archive old files and comes across a box dedicated to Richard Shanaman’s illegal poker games. The box dates back decades ago and is dated the same night as infamous hotel fire. Inside the box are old poker chips and a charred clutch. Jared finds the clutch so unusual because women were banned from joining the underground poker games during that time. Inside the clutch, Grace finds a name of who it once belonged to.
George finds Cassie in the dining room and notes her forlorn expression. He knows that she is worried about Sam while he is away. George also knows that Cassie’s worry comes from the fact her last husband died way before his time. Cassie says it is what she gets for falling in love with men who want to change the world.
Grace finds Martha at City Hall and shows her the photo of her great-grandfather receiving the hero’s medal for saving lives in the burning fire. Martha rolls her eyes now that she knows her great-grandfather lied and really was at a Cubs game the same night he claimed to have rescued people in the fire. But Grace points out that the woman next him in the photo is her great-grandmother, whose clutch was found in the belongings of the burning building. Back then, Martha’s great-grandmother couldn’t admit that she was the one gambling that night; she had to protect the family name. Martha is excited because that means the Endicott Street should remain as is because her family name is still intact.
Sam calls Cassie at the shop to give her an update on his time in Colombia. He thanks her for looking out for him. When Cassie wants to know what she did to help, he tells her that she knows what she did. Sam also tells Cassie he will be home the next night.
Cassie finds out that when Nick made the delivery for Stephanie at the Bistro, he also helped change the customer’s lightbulb. After that, he delivered the woman’s thank you cookies to the local homeless shelter, even volunteering there for a couple of hours that evening. Nick says it was just a distraction to put off his college applications. Cassie points out that maybe Nick really gets joy from helping people; he is a lot like his father in that way. Cassie tells Nick that no matter what his career path is, he will be changing the world for the good.
Back at the Old Mill, Abigail asks Phil why he wanted to return. He tells her it is because the Old Mill happens to be one of the most romantic spots in town. Phil also surprises Abigail with the news that he bought the Old Mill to move his company’s headquarters in and he is ready to call Middleton home. Abigail responds with a smile.
Cassie waits up for Sam to get home and greets him with a big hug. Sam is happy to see that Nick has finally filled out all of his college applications why he was gone. Cassie opens up to Sam about her fears and vows to love him as if every day was their last day. Sam says it sounds like the perfect way to start a life together. Cassie has one more surprise: she has chosen a wedding date and it is less than three weeks away!