The Midwest's 5 Best Festive Train Rides Make The Holidays Unforgettable

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If you're looking to create holiday memories or start a new tradition, consider taking a winter train ride through some of the Midwest's most historic regions. A number of vintage railroad companies offer cozy Christmas and New Year's train excursions, during which passengers can warm up with some hot cocoa, wine, and holly-jolly magic. Thanks to the Midwest's railway history, many of the region's festive seasonal trains offer a glimpse into the past. Each one is meticulously maintained to capture the nostalgic experience of a bygone era while setting the perfect festive tone.

Many of these holiday train trips are geared toward families with little ones. As such, several include meet-and-greets with Santa. Others offer Christmas cocktails and live music for adults. If your New Year's Eve tradition of watching the Times Square ball drop on television needs a little upgrade, December 31 is also a great time to hop aboard. A handful of these trains serve up dinner, music, libations, and fireworks for a unique way to ring in the new year with a bang.

A favorite of Samantha Brown, the Black Hills of South Dakota offer some unparalleled scenery and a history of train travel. In 1874, gold was found here, and train routes quickly expanded in order to establish mining camps. By the 1940s, diesel started replacing steam engines, and a need to maintain this important part of history was recognized. As a result, the Black Hills Central Railroad created the 1880 Train to preserve steam locomotives. Throughout the 1970s, the train featured in several Hollywood films. Today, the railroad operates three steam and two diesel engines on picturesque excursions to Keystone (aka the "playground of the Black Hills").

During the holidays, a special one-hour round-trip ride to the "North Pole" is offered for families between the end of November and throughout December until Christmas Eve. The Holiday Express train departs from Hill City (a hidden paradise in South Dakota's mountains) and includes hot chocolate, sugar cookies, candy canes, and visits with Santa and Mrs. Claus. Tickets cost $46 for adults and $29 for kids. Passengers aged 21 and older can opt for a "spiked" ticket ($69 per person) aboard a different passenger car where the cocoa features peppermint or butterscotch schnapps in a souvenir take-home mug.

The Hocking Valley Scenic Railway dates back to 1862, when it was created to transport coal and salt out of Columbus, Ohio. Nowadays, the railroad primarily operates vintage diesel trains for passengers. However, the company occasionally runs one coal steam-powered locomotive. Routes are available between the depot in Nelsonville (a brick-paved city with a buzzing art and music scene) and Logan (an enchanting gateway city full of cozy Midwest charm), passing several historic sites along the way.

On December 31, the railroad offers a New Year's Eve Train that heads to East Logan and back on a two-hour journey. There are two seating options: one with pizza and soft drinks for families and a second with alcoholic beverages for adults only. Right before midnight, the train stops so that passengers can step off to watch a brilliant fireworks display before returning to the station. Tickets are $36 for adults and $25 for kids. For $38, adults can buy a ticket with wine and cheese included.

The Wisconsin Great Northern Railroad is one of the Midwest's best-kept secrets. Based in the northern Wisconsin town of Trego, the railroad's routes pass the magnificent Namekagon River. During evening runs, LED lighting is visible under the train cars. For the holidays, the company takes a modern approach to festive train rides by offering a pizza party with Santa for little ones throughout the month of December. The two-hour-long Santa Pizza Train ride includes visits with Santa, pizza, a cookie, and hot cocoa. Tickets are $40 for kids and $50 for adults.

For $75 per person, there's also a new Holiday Wine Train option in the adults-only lounge car on the trip. The experience includes a bottle of wine from the award-winning Door Peninsula Winery, famous for its fruit wines from cherries, blackberries, pears, and yes, grapes too. During the ride, visitors can also enjoy appetizers, a tumbler to take home, and a toast with Santa. The train cars get decked out for the event, so passengers can roam the cars to explore while listening to holiday music.

Ring in New Year's early on My Old Kentucky Dinner Train (part of the R.J. Corman Railroad Group), which specializes in themed excursions like murder mystery dinners, bourbon sampling excursions, and holiday trips. The 37-mile journeys pass by the Jim Beam distillery, the Jackson Hollow Trestle, and Jesse James' safe house. There are also seasonal menus for passengers to enjoy during the experience.

For the New Year's Eve Celebration Excursion, the train departs from a station in Bardstown (the Kentucky town famous for being the bourbon capital of the world) for a three-hour round-trip dinner ride. The outing begins at 6 p.m., so you can still catch the ball drop after dinner. As soon as you board the 1940s vintage rail car, you'll be presented with champagne, cocktails, and hors d'oeuvres for social hour. Afterward is a four-course meal and live musical entertainment, plus a mock countdown to honor the arrival of 2026. To spice things up a little with some friendly competition, there's a "best dressed" contest with prizes for the winners. Tickets are $149.50 each, and two-person private tables are available for $299 per guest.

When "The Polar Express" children's book was published in 1985, it became a Christmas icon alongside other legendary stories like "How the Grinch Stole Christmas." The tale follows a magical train journey to the North Pole, and after becoming a hit film in 2004, it inspired railroads across America to capture this experience in real life for kids. Coordinated by Rail Events Inc., the one-hour Polar Express train ride is now available in 40 locations across the United States throughout the holiday season. Dates and ticket prices vary depending on location.

Just like in the book by Chris Van Allsburg, kids aboard the train are given golden tickets, which the conductor collects. Next comes hot chocolate and a reading of the story. Santa then boards the train for a meet-and-greet with little ones, who also get a souvenir silver bell to take home. In the Midwest, the Polar Express train trip is available in Branson and St. Louis, Missouri; Stearns, Kentucky; Connersville and French Lick, Indiana; Dennison, Ohio; and Monticello, Illinois.

In researching these top Midwestern train rides, we wanted to include various holiday trains with special events for Christmas, New Year's, and beyond. This search included looking for excursions that could appeal to children and adults. As a franchise, the Polar Express trains offer a similar experience in many destinations, so we also wanted to highlight railroads with unique festivities. With these considerations in mind, we discovered pizza parties, dinner shows, and musical entertainment aboard historic railroads.

To narrow down this list to just the five best holiday train rides, we explored those highlighted by publications such as Travel + Leisure and region-specific resources including Midwest Weekends. From there, we checked to see which options had not yet sold out. Additionally, while Christmas train rides are fairly common, we only found a handful of trains offering New Year's Eve experiences. However, these really stood out as a wonderful way to ring in the new year, so we included them on our list.

Of course, Christmas and New Year's aren't the only notable end-of-year celebrations. A few Hanukkah-themed excursions are also available in the U.S. For example, Felton, California's Roaring Camp Railroads company hosts an annual Chanukah Train near Santa Cruz. Festive travelers can also visit some of the most magical towns across America for other holiday celebrations, like Winston-Salem, North Carolina's seasonal downtown parade, which pays homage to Christmas, Hanukkah, Kwanzaa, the winter solstice, and Yule.