The entire Wahlberg clan gears up for their favorite local holiday, Dorchester Day--an event that has become the backdrop for some of the family's most infamous pranks. While Paul insists that the family forgoes the hijinks this year, his nephew Brandon has other plans--and he has his sights set on Paul's assistant, Kari. Meanwhile, Donnie enlists Johnny "Drama" and Henry "Nacho" to paint a shed in his backyard while he's away on tour and the process becomes a joke all its own.