While Ned and Sean are out of town in Frankfort, Jeremy finds himself in over his head with a poker debt. And in order to pay off his debts, he throws together an evening of gambling at the house, with the help of Clay, Alice, and Lexy.
As the 14th annual running of the Lexington Stakes draws near, the Logan's prize thoroughbred Gauntlet remains the horse to beat. News of Gauntlet's impressive practice times has even reached as far away as Europe.
Marita is romanced by a handsome young businessman, who quickly wins Isaac's approval. Meanwhile, Sean attempts to buy land for a new hospital but his plans are threatened when Vivian's mother, Georgina, returns to seek revenge on the Logans.
When Ned publicly rejects Georgina, she begins to plot revenge on the Logans. Meanwhile, Helene slips a knockout powder into Jeremy's drink and later accuses him of rape, causing William to challenge him to a duel.
Ned comes to the aid of a mysterious young woman, when her buggy crashes, and he falls in love with her. Meanwhile, Clay and Vivan's relationship begins to blossom, at the same time that Jeremy and Alice's begins to fade.
Ned's new wife, Charlotte, causes turmoil in the family when she meddles with Sean's accounting records, fueling him to move out of the house. Meanwhile, a frustrated Jeremy turns to Molly when Alice puts their relationship on hold.
When Clay courts Vivian, he finds himself spending less time preparing Gauntlet for the upcoming Kentucky Derby. Meanwhile, Charlotte schemes to buy a gifted race horse and Jeremy & Molly find an investor for their new business.
While Ned plans an extravagant masquerade ball for his bride, Charlotte, Clay and Jeremy set off for Richmond in search for the truth about Charlotte's identity and past.