Horse-Drawn Carriage and Holiday Trolley Rides for Festive Family Fun

Outdoor Places to GoWinter

Start a new tradition of old-fashioned family fun this holiday season: take a horse-drawn carriage or trolley ride together! Sipping hot cocoa while snuggled up with the kiddos in a carriage amidst a cool, wintry night . . . doesn’t that sound just magical? And there are some amazing events lined up locally that feature this classic tradition to make sweet winter memories together. Check them all out here!

2022 Old-Fashioned Carriage and Holiday Trolley Rides

Long Grove Vintage Holidays (Long Grove)
November 19-20, 25-27 and December 3-4, 10-11, 17-18
Vintage horse-drawn carriage rides to all the quaint shops brimming with old world charm in historic downtown Long Grove. Local merchants will be featuring special sales, food and drinks. You’ll find holiday caroling and a visit from Santa on select weekends, too.

Holiday Lights Tours (Naperville)
November 25 – 27, 2022 and December 1-27, 2022 (closed on Christmas) | 5:00 pm – 10:30 pm 
Trolley to/from the Christkindlmarket in Aurora on Thursdays: December 1, 8, 15, 22, 2022
For over 25 years, Naperville Trolley has offered holiday light trolley tours to see all the beautiful homes lit up around town. Timeslots are available for public and private tours. Some dates are booked already; be sure to check online to see dates that are still available.

Holiday Walk & Market (Clarendon Hills)
December 2, 2022 | 5:00 pm – 9:00 pm (horse-drawn carriage rides begin at 7:00 pm)
Kick off the holiday season with the village tree lighting at 6:00pm, followed by a Christmas Walk and Holiday Market complete with carolers and horse-drawn carriage rides starting at 7:00pm. Roasted chestnuts, hot chocolate, mulled cider, and a Santa appearance at 6:30pm. Grinch and Scrooge photo opportunities, too.

Deck the Depot (River Forest)
December 3, 2022 | 9:00am – 2:00pm
This festive trolley ride around town includes a Polar Express storytime, holiday hunt, and sweet treats. On top of that, you’ll find a hot chocolate bar, crafts, and pictures with Santa, too. Limit six tickets per household.

The Santa Trolley (Oak Park)
December 4 and 11, 2022
Starting at the Oak Park Conservatory, passengers aboard the Santa Trolley will play games and sing songs on the way to see Santa and Mrs. Claus at the Cheney Mansion. Drinks and cookies complete the journey. Space is limited, so be sure to register in advance.

Holiday Trolley Express (Prospect Heights)
December 14, 2022
Venture through the neighborhood aboard the holiday trolley express and see all the houses decorated for the season. Register in advance for your ride, which includes storytime with one of Santa’s helpers and a visit with Santa upon return. There will also be a craft and treats for the kids, too.

Holiday Trolley Rides (Bloomingdale)
December 15, 2022
Ride to Old Town Park on the holiday trolley to see the festive lights! Onboard, trolley-goers will listen to a story, sing songs, and enjoy a Santa visit. Upon the return to the Johnston Recreation Center, each family will receive a treat bag, kids can make a holiday craft, and light refreshments will be served. Register each family member in advance.

Holidays in Hinsdale
Check back; 2022 info to come.
Enjoy horse drawn carriage rides, boutique and holiday shopping, gingerbread cookies, and visit Santa Claus at Burlington Park.

Check out all the cool ideas and inspiration for kid-friendly holiday fun this season (we’re always updating, too!) And, if you’re in the mood for more festive, holiday rides, be sure to peek at our list for 2022 Polar Express Train Rides!

Join the List

Let us help you plan fun days!
Get kid-friendly updates straight to your inbox

"*" indicates required fields

When would you like to receive Kidlist emails?*
This field is for validation purposes and should be left unchanged.

Related Articles

About the Author

Leave a Reply

Your email address will not be published. Required fields are marked *

Fill out this field
Fill out this field
Please enter a valid email address.

Our Amazing Sponsors
Popular Guides