Successful and fiercely independent, Mary Ann Brubeck (Vandervoort) adopts a baby girl to raise on her own just before Christmas. Due to weather, she and the baby get stuck in Bethlehem, PA for the holidays. When there is no room at the inn, her only option is to stay with the innkeeper’s brother Joe (Ayres), a quintessential bachelor who lives in a house that he treats like a barn. As Mary Ann learns the value of community by spending time with Joe’s family and participating in the local church’s Christmas events, Joe starts getting his act together with new motivation…and the two begin to see each other in a new light.
Just one week before Hanukkah, corporate lawyer Tory finds herself unexpectedly unemployed and questioning what’s next. As she helps her Bubby prepare for the holiday, she embarks on a quest across Chicago to find the last box of coveted Hanukkah candles. Her search leads her to Rocky's, an Old Town bar, where she encounters Jay, a charming doctor from Florida, his grandfather Sam, and a cast of quirky regulars who make her rethink everything. Torn between keeping her job loss a secret and embracing a newfound sense of belonging, Tory ends up bartending at Rocky's, transforming it into the vibrant "Hanukkah on the Rocks" celebration. Through festive food, drinks, and games, she revitalizes the bar, bonds with Jay, and finds the courage to pursue her true calling. As Tory navigates the holiday, she learns that sometimes a detour can lead you exactly where you’re meant to be, lighting the way to a future filled with joy, romance, and self-discovery.