When Karl and Nicole hosted their first New Year's party, they never imagined it would become a recurring holiday tradition with the same college friends for the next ten years. But when Karl's brother Mike dies in a head-on collision on his way to Karl’s house for the celebration, their hodgepodge group of party guests finds themselves bonded forever through an unexpected shared trauma. To honor Mike's memory, they make a pact to hold a New Year's Party each year, no matter what the circumstances.

After a string of bad relationships and a canceled graduation trip, Bobbi gives up and heads home for Christmas. Despite the magnetic pull of holiday lights and hot cocoa in the square, she’s still solidly committed to landing her dream film internship in LA and putting any distractions decidedly in the slush pile. Ben, a highly sought-after ski instructor—and Bobbi’s first kiss—is back in Sugar Creek for one reason and one reason only: to spend one last Christmas with his mom before she loses her battle with ALS.

College student Toby is desperate for direction. Pausing his higher education, he relocates to Portland and rents a townhouse in hopes of reconnecting to his roots. But he didn't expect his passion for soap operas to lead to the relationship he's always needed. At 87-years-old, Jo's mind and body aren't what they used to be. But even at her senior age, she's sharp enough to know her nursing aids are after her generous family trust. So when a kind and honest young man moves in next door, she quickly enlists his help in catching the sneaky bandits.

When Julie Green’s ailing grandmother asks her to arrange one last party at the old Inn she used to run, Julie can’t say no even though the last thing she wants is to leave the city for middle-of-nowhere Vermont. Even worse, Cozy Holly Inn is in disrepair, there’s a persnickety cat hiding in the basement and the family of grinches who own the competing inn down the street seem determined to ruin her chances of success.

It’s been five years since Evelyn’s beloved husband passed, but the 55-year-old is stuck in the past. Evelyn’s sister has had enough, so she buys her a trip to their old summer getaway, Martha’s Vineyard, where Evelyn learns she’s not alone after meeting Wanda, a divorcee with a secret, and Bitty, a sassy widow. As the three women make fast friends, they help each other learn how to move forward and start living again. So when Evelyn sees that her longtime dream home is on the market, she doesn’t hesitate.