It’s Thursday morning in Wilby. Dan Jarvis (James Allodi), a transplanted Mainlander and owner of the local video store, is clearly troubled as he climbs to the top of a small bridge over a rushing river, apparently ready to end it all. However, before he can make his fatal leap, Duck MacDonald (Callum Keith Rennie) appears. Duck, an Islander born and bred and a man of few words, is the local handyman.

Thwarted, Dan leaves Duck to his own work on the bridge: hanging a large banner. The banner reads “Wilby Wonderful,” announcing the upcoming Wilby Days Festival. The festival is the brainchild of Carol French (Sandra Oh), a tightly-wound real estate agent and professional volunteer. Carol is, like Dan Jarvis, a non-Islander, but she has made it her focus to find her way into the inner circle of Wilby’s elite, although so far, not very successfully. Her most recent scheme is to sell the stately old home of her recently deceased mother-in-law to Wilby’s good-natured but perk-loving Mayor, Brent Fisher (Maury Chaykin).

Carol’s husband, Buddy French (Paul Gross), could help Carol in her quest to becoming an insider, but he finds Brent and his cronies uninteresting, to say the least. Worse, Buddy is beginning to find that Carol’s pursuits are turning her into a stranger. Carol senses this, but the fear of her marriage falling apart only makes her spin her wheels even more.
These same fears are starting to push Buddy into the arms of the hopeful and willing Sandra Anderson (Rebecca Jenkins). Sandra is a true Island girl with an easy laugh and an incredible lust for life. She recently returned to Wilby after years on the mainland. She has taken over Iggy’s, the once popular but now abandoned local café. Despite good intentions, she hasn’t managed to get the kitchen running much past coffee and donuts.

Sandra’s main reason for returning to the island was to give her teenage daughter Emily (Ellen Page) a chance at a simpler life. Emily, on the other hand, thinks the reason for returning to Wilby had more to do with her mother having slept her way through every town on the mainland.