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Excitement runs high in the Whistling Pines Retirement community as the first annual Two Harbors Buccaneer Days celebration approaches. The city asks local fraternal clubs and the city band to move their summer events to the weekend of the festival. To entertain the expected throng of tourists, the city announces a Norwegian lutefisk toss, band concerts, food vendors, and a Lake Superior sailing regatta. Peter Rogers, the Whistling Pines recreation director, announces activities to mirror the town's plans including a pirate costume contest and a sea shanty singalong. A shadow is cast over the celebration when one of the regatta competitors is found dead on his boat. Peter is drawn into the murder investigation by the new police chief despite his wife's advanced pregnancy and his struggle to quash rumors about a senior citizens naturist cruise, with half the residents anticipating a bird-watching outing and the rest expecting to sunbathe on a clothing-optional cruise.

When Hagstrom's bait store burns down, arson rumors fly among the residents of Whistling Pines senior living facility. When Peter Rogers, the recreation director speaks with residents he discovers there have been numerous suspicious business fires over the years. Torn between two sets of Halloween preparations and the arson investigation, Peter finds himself drafted as an unwilling judge for Two Harbors Halloween competitions, while the police chief forges ahead with the arson investigation.What is alpaca bingo? Will the Rube Goldberg cannons actually launch a pumpkin without killing anyone? Will Peter survive a night of surveillance with the fire chief?