From Sioux Falls, head north on Interstate 29 to the Strawbale Winery. During November and December, there is the option to enjoy "Twilight Flights" which include hors d'oeuvres, dessert and wine along with a helicopter flight.
Get back onto Interstate 29 and go north to Watertown. This hometown of artist Terry Redlin is also home to the Lake Area Technical Institute Holiday Festival of Trees (late November). Come see the Christmas trees and also enjoy a free viewing of the famous paintings at the Redlin Art Center.
From Watertown, head west to Pierre. South Dakota's capital city hosts a great holiday treat with the Christmas at the Capitol celebration (Thanksgiving through Christmas). During this free event, the State Capitol is filled with Christmas trees and holiday cheer. Overnight in Pierre/Fort Pierre.