The story revolves around Ankur (Kay Kay Menon) & Rimli (Sonali Kulkarni), a recently married couple on their honeymoon in Darjeeling. But on the eve of their return to Calcutta, Ankur disappears. The Inspector in charge, Robin Bose, searches high & low, but Ankur is no where to be found. When he questions Rimli, the only clues she is able to give him, are of a taxi driver Ankur had fought with & a mysterious looking man whom she thought was following her throughout their trip in Darjeeling. The mystery returns to Calcutta one night...via Darjeeling. Faces are unmasked and new ones emerge. Two years later, Inspector Bose relates this story to a few friends; they are intrigued by this story, & question him about the outcome. But he has no answers. The friends start gossiping on a rainy night, bantering & discussing the mystery of the missing husband amongst them. Intrigued by this story, they start a tale about the possible outcome and all take part to give their own versions where personalities, motif and professions change. The past and the future come rushing back and the characters in the room blend in to the 'story' themselves giving it a new turn, every time.
Via Darjeeling is set in modern day Calcutta & Darjeeling and is based on an age old Bengali tradition called 'adda' where friends get together in the rains, & exchange stories & gossip, over drinks & dinner.
The film goes through several peaks & twists in its narrative, opening itself up to new meanings, interpretations and solutions, leading from one to another, with some what diverse ends!