Starting in Sioux Falls, go downtown in the evening and sip a cup of your favorite hot coffee, tea or cocoa at one of the many coffee shops. Once the sun sets, head a few short blocks to Falls Park. Take in the magic of millions of Christmas lights on display during Winter Wonderland at Falls Park mid-November through December. While in Sioux Falls, be sure to hit one of the many fine dining restaurants. A wide variety of cultural entertainment and shopping options are also available in South Dakota's largest city. Overnight in Sioux Falls.
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.
From Pierre, travel south on Highway 83 to Interstate 90 and head west. On your way to the Black Hills, take a drive through Badlands National Park. Experience this unique and awe-inspiring landscape while it has a dusting of snow to enhance the beautiful colors. After your drive through the Badlands, get back on Interstate 90 and continue west to Rapid City. While in South Dakota's second largest city, go downtown for the Festival of Lights Parade (late November) and take in holiday cheer with the locals, or enjoy Winter Market at Main Street Square (Saturdays in December). Overnight in Rapid City.
From Rapid City, depart on Highway 16 south to Mount Rushmore National Memorial. View America’s most famous faces in the crisp winter air. Then travel south on Highways 16/385. The next stop is Crazy Horse Memorial, the largest sculptural undertaking of its kind, where you can also visit the Indian Museum of North America and the sculptor’s studio. Then head to the Wildlife Loop Road in Custer State Park to watch for buffalo, elk, deer, antelope and burros. From there, continue traveling south on Highway 385 through Wind Cave National Park to Hot Springs. Overnight in Hot Springs.
While in Hot Springs, take a dip in the natural, indoor warm-springs swimming pool. Then tour The Mammoth Site, where Columbian mammoths fell into a sinkhole 26,000 years ago. Their bones are preserved where they fell. Depart north on Highway 385 for Deadwood for A Grand Christmas at Deadwood Mountain Grand (late November through late December). To try your luck at gaming or learn about the history of this gold rush town. Overnight in Deadwood.
Spend the day riding snowmobiles through the northern Black Hills, where you can tour scenic Spearfish Canyon and Roughlock Falls Nature Area. Another option is a ski trip to one of the ski areas for downhill and/or cross-country skiing. After skiing, head back to Deadwood for more evening excitement. Overnight in Deadwood.