Travel Trip Ideas Around the Midwest Festive Trains to Ride This Holiday Season All aboard! Holiday magic and memories await. By Shelby Deering Shelby Deering Shelby Deering is a lifelong Midwesterner residing in Madison, Wisconsin. Her travel features have appeared in publications like USA Today, HGTV Magazine, Country Living, The Pioneer Woman, and Experience Wisconsin, and she has written for the Wisconsin Department of Tourism as well. When she's not writing, you'll find her exploring Madison's (many) trails with her husband and corgi, Dolly, or perusing a flea market. Midwest Living's Editorial Guidelines Updated on October 20, 2023 Throughout November and December, scenic trains across the Midwest transform into decked-out, magical locomotives bursting with cheer. These family-friendly holiday train rides are short and sweet, ranging from hour-long jaunts to two-hour voyages, and often include Christmas treats, dazzling decorations, enchanting music and visits with Santa Claus. Courtesy of CTA Allstate CTA Holiday Train, Chicago Who knew everyday transportation could become oh-so jolly in a flash? Between Thanksgiving and Christmas, the Chicago Transit Authority (CTA) pulls out all the stops with its Allstate CTA Holiday Train. The Holiday Train runs on all eight lines, and each car is dressed up in sparkling lights and seasonal decor. (Bonus: Santa warmly greets guests as the train pulls into the station.) During the season, the Holiday Train delivers more than 600 food baskets to charities all over the city. Unique Midwest Light Displays to See This Winter 1880 Train Holiday Express, Keystone, South Dakota Children won't believe their eyes as they voyage from Hill City, South Dakota, all the way to the North Pole. This one-hour, round-trip ride on the historic 1880 Train includes memorable visits with Santa and Mrs. Claus, free bells that your little ones can ring, and hot cocoa and sugar cookies. For a grown-ups-only experience, try the 21+ "Holiday Express Spiked" with spiked hot cocoa in a souvenir mug. Tom Fleming East Troy Railroad Christmas Trains, East Troy, Wisconsin Discover a variety of seasonal train excursions at East Troy Railroad, just 20 minutes from Lake Geneva. The two-hour Daytime Christmas Trains run between the East Troy Depot and Santa's Workshop at The Elegant Farmer, a year-round farmers market. On Santa's Special Evening Trains, passengers enjoy hot chocolate and cookies in first-class dining cars on the way to Santa's Workshop (kids receive a holiday book and stuffed animal too). Coopersville and Marne Railway Santa Train, Coopersville, Michigan This vintage train in Michigan travels along a track originally laid in 1858, and each winter season, it sparkles with Christmas spirit. Kids love the 90-minute Santa Train ride, which includes a princess reading holiday-themed books, carol singing, festive decorations and of course, an appearance by Kris Kringle. Little ones will even pick up some special free gifts along the way. 15 of the Best Outdoor Winter Activities and Festivals Around the Midwest Courtesy of St. Louis Union Station St. Louis Union Station The Polar Express Train Ride, St. Louis If The Polar Express is a go-to bedtime story during the holiday season, this experience will really bring its pages to life. The Polar Express's one-hour journey from the St. Louis Union Station Train Park to the North Pole is set to the soundtrack of the beloved film. Don your favorite Christmas pajamas for the occasion and cozy up with mugs of hot cocoa and cookies until St. Nick boards the train with gifts in tow. Great Places to See Midwest Holiday Lights Hocking Valley Scenic Railway Santa Train, Nelsonville, Ohio For decades, Nelsonville's Santa Train rides have combined Christmas nostalgia and snow-blanketed views of Hocking River Valley. The two-hour journey from the Nelsonville Depot to East Logan and back features holiday music, candy canes and face time with jolly old St. Nicholas. Was this page helpful? Thanks for your feedback! Tell us why! Other Submit