Struggling to keep the family house, the Winthorpe siblings take in a woman on the run who has recently come into a large sum of money under mysterious circumstances.

Lifelong best friends, Maddy and V, set out for a relaxing vacation. When their old college clique hijack their plans, V finds herself at a remote ski lodge where a group of mysterious wealthy men throw a celebration century in the making.

Katherine Watson is a recent UCLA graduate hired to teach art history at the prestigious all-female Wellesley College, in 1953. Determined to confront the outdated mores of society and the institution that embraces them, Katherine inspires her traditional students, including Betty and Joan, to challenge the lives they are expected to lead.