These Local Holiday Trolley and Horse-Drawn Carriage Rides Are Pure Old-Fashioned Christmas Magic

Outdoor Places to GoWinter

Start a new tradition of old-fashioned family fun this holiday season: horse-drawn carriage rides or trolley rides! Sipping hot cocoa while snuggled up with the kiddos in a carriage to admire the Christmas lights on a winter’s night . . . doesn’t it sound just magical?

There are some amazing events lined up locally that feature this classic tradition to make sweet winter memories together. Check them all out here!

Horses pulling a carriage so families can take carriage rides

Long Grove Vintage Holidays (Long Grove)
Weekends starting November 19, 2023 through December 18, 2023
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 24 – 26, 2023 and December 1-27, 2023 (closed on Christmas) | 5:00pm – 10:30pm 
For over 25 years, Naperville Trolley has offered holiday light trolley tours to see all the beautiful homes lit up around town. Time slots 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 1, 2023 | 5:00pm – 9:00pm
Shopping, food, and drinks at this annual event. More details to come on 2023’s festivities.

Deck the Depot (River Forest)
December 2, 2023 | 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 of six tickets per household.

Holiday Celebration (Brookfield)
December 2, 2023 | 10am – 6pm
Seven trolley stops around Brookfield with loads of festivities planned throughout the day including snow globe pictures, Elsa and Anna meet & greet, petting zoo, wood carving, holiday music, treats and more!

The Santa Trolley (Oak Park)
December 3, 2023 | 1:15pm-2:45pm
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.

Dickens Christmas Dinner (Oak Brook)
December 8, 2023 | 5:00pm – 9:00pm
Horse-drawn carriage rides around the property and carolers set the mood while you dine at The Drake Oak Brook.

150 Years of Hinsdale for the Holidays
December 9 & 16, 2023 | 11:00am – 2:00pm
A free festive event in Burlington Park that features horse-drawn carriage rides, gingerbread cookie decorating, and visits with Santa. 

Holiday Express (Oak Brook)
December 10, 2023 | 2:20pm – 5:00pm
Ride to the North Pole (Central Park West) on a festive trolley ride from the Family Recreation Center to meet Santa! Crafts, bounce house, light refreshments and more. Register in advance.

Holiday Trolley Express (Prospect Heights)
December 13-14 | Time slots between 4 and 8pm
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, cookies and cocoa for the kids, too.

Holly Jolly Trolley (Hinsdale)
December 14, 2023 | 5:00pm – 9:00pm
Tours begin and end at Immanuel Hall (302 S. Grant Street) at this event hosted by the Hinsdale Historical Society.

Holiday Carriage Rides (Bloomingdale)
December 18, 2023 | 6:00pm – 8:00pm
Ride in an old-fashioned carriage through Old Town Park’s Festival of Lights. Carriages seat a maximum of four adults or two adults and three children. Time slots begin at 6pm. Register in advance. Note that blankets are not allowed on the carriage rides.

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 2023 Polar Express Train Rides!

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