It's Rebecca's (Rachel Dratch) 50th birthday weekend in WINE COUNTRY. Self-appointed "tour director" Abby (Amy Poehler) has orchestrated the trip from top to bottom, minute by minute. Always a little uptight, Abby can't help but be disappointed when the others aren't as gung-ho as she'd like them to be. For instance, Catherine (Ana Gasteyer), a successful restaurateur, can't tear herself away from her cell phone; Naomi (Maya Rudolph), a committed mom, is silently distracted by impending medical news; Val (Paula Pell) is dealing with loneliness and a broken heart; and Jenny (Emily Spivey, also one of the film's writers) isn't sure she even wants to be there. Still, expectations are high; wine is flowing. The appearance of the rental's owner (Tina Fey) and a "chef" who comes with the house (Jason Schwartzman) bring even more eccentricity to the already heavily populated table. Over the long weekend, mini-conflicts arise, personal struggles are slowly revealed, and the women's loving connectedness is tested to the extreme.