When the Edgartown building inspector discovers that Leo is living above the bookstore, he threatens to fine George for violating a zoning ordinance. Leo convinces George to slip the inspector an envelope full of cash, which lands George in jail. George clumsily attempts to bribe a public official and lands in jail. When the Edgartown building inspector discovers that Leo is living above the bookstore, he threatens to fine George for violating a zoning ordinance. Leo convinces George to slip the inspector an envelope full of cash, which lands George in jail. Meanwhile, Casey and Ted don't know how to fire an incompetent waiter.

A grab bag of fears makes Halloween night on the Vineyard a real scream. It all starts with a ghost story told by Ambrose at the bookstore, which leaves a superstitious Leo convinced he's not the only one haunting the place. Meanwhile, George faces his annual fear: running out of Halloween candy and incurring the wrath of angry trick-or-treaters. And Ted and Casey, afraid for their sanity after spending too much time together, decide that Casey needs some R&R. But when she retreats to The Harbor Inn, her respite is disturbed by a group of pro wrestlers — and by some other unwelcome intruders. When several books mysteriously disappear and lights begin to turn themselves off and on, Leo is convinced that the ghost of Rumsey Reeve, the headless sailor, has come back to haunt the bookstore. Meanwhile, George stocks up on generic candy, since he's heard that the neighborhood kids take the expression ""trick or treat"" very seriously. Unfortunately, a nervous Ted eats all the candy, leaving Ge

Secretive Sheila shows up one day in the bookstore, and George is somewhat stunned when she asks him out on a date. So is Leo, because he can't shake the nagging feeling that he and Sheila have met before. George's date is cut short when Leo finally remembers the shocking truth about Sheila and an old chapter in his life.

George hosts a tour of his home in period costume in hopes of becoming President of the Historic Conservancy, but his high hopes of finally winning the annual historic house tour end in a drunken haze after Leo and Ambrose spike the egg-nog.

While he is reminiscing about Casey's childhood on the eve of her baby shower, Leo remembers that he convinced his old friend Robert Goulet to sing her a song on her seventh birthday. Eager to make a big splash at the shower, Leo tries to get Goulet, who is making a guest appearance at George's bookstore, to sing for Casey again. Unfortunately, this time, the song produces more than just applause.

Ted and Casey hire a nanny to care for their new baby, Alice, who seems to be the perfect person to care for the new baby. She's a registered pediatric nurse, warm, smart and loving. The problem is she's a little too loving when it comes to Ted. When Alice, mortified by her crush, decides to quit, it's up to George to figure out a way to keep her on the island and away from Ted.