A weekend at an English country house: English Fern by Penhaligon's, or possibly Hammam Bouquet by the same
A night in Manhattan: Musc Ravageur by Frederic Malle
A walk through Vermont woods: Noir Epices by Frederic Malle, or Leonard Pour Homme by Leonard, or Magie Noire by Lancome
An afternoon on the beach in Provincetown: Neroli Sauvage by Creed
Feeling playful on a Sunday morning: Define playful. For "frisky" fun I would put on Donna Karan's Black Cashmere. For "other" fun I'd probably put on Vetiver Extraordinaire by Frederic Malle.