Horse-Drawn Carriage and Trolley Rides for Old-Fashioned Holiday Fun

In the midst of the busy holiday season, wouldn’t it be nice to slow down with your loved ones on an old fashioned horse-drawn carriage ride or holiday trolley trip? There are loads of festivals in the area offering rides all around town. We have the low-down just for you! Bundle up your kiddos and get your hot cocoa ready for a memorable ride with the family.

This article is sponsored by Oak Brook Park District.

2019 Old Fashioned Carriage Rides
and Holiday Trolley Rides

December Holiday Lights Tours (Naperville)
Dates beginning November 5, 2019
$20 for public tours. Travel around beautiful Naperville to see all the lovely homes decked out in Christmas lights. Many dates are booked already, see dates still available.

Holly Trolley (Elmhurst)
November 20 – December 28, 2019 | 10:00 am – 10:00 pm
Hop on for some holiday fun — no tickets required. The Holly Trolley will connect residents to three shopping districts hosting many holiday events.

Miracle on Martin (Homewood)
December 6, 2019 | 5:00 pm – 9:00 pm
Ride in a musical trolley around town while enjoying costumed carolers, a tree lighting ceremony, live ice-sculpting demos, photos with Santa, hot cocoa by the bonfire, and more.

Christmas Walk (Clarendon Hills)
December 6, 2019 | 6:00 pm – 9:00 pm 
Watch the lighting of the Christmas tree and enjoy free food/drinks from local businesses, including warm chestnuts. Horse-drawn carriage rides, Victorian carolers, ice sculpture artists and Santa will round out the night.

Family-Friendly Weekend Events: October 23–25 and Beyond

Holiday Express at Blackberry Farm (Aurora)
December 6, 2019 (Special Needs Night) | 5:00 pm – 8:00 pm
December 5, 12, 13, 19 and 20, 2019 | 5:00 pm – 8:00 pm 

December 7, 8, 14, 15, 21 and 22, 2019 | 2:00 pm – 7:00 pm
Holiday lights, music, crafts, story time, food and drinks make up this festive evening, as well as a visit with Santa. A holiday hay ride or a festive train are both options for further explorations of Blackberry Farm. Tickets on sale starting November 12, 2019.

Hometown Holiday (LaGrange)
December 7, 2019 | 3:00 pm – 8:00 pm
Free holiday matinee featuring Elf at La Grange Theatre, choir/dance performances, free petting zoo, pony rides and trolley rides. Don’t miss Santa’s arrival to town for the big tree lighting ceremony.

Santa Trolley (Oak Park)
December 8 & 15, 2019 | Various time slots available
Start at the Oak Park Conservatory for a special display, then travel via trolley to see Santa and Mrs. Claus at the Cheney Mansion. In addition to entertainment, there will be milk and cookies before everyone hops back aboard the trolley.

Holiday Hayride (Palos Heights)
December 13, 2019 | 6:30 pm – 8:00 pm and 7:30 pm – 9:00 pm 
Carols and a trip around Palos Heights on a festive hay wagon. Warm up with food and make crafts at the nature center afterwards. $10/person, registration required.

Oak Brook Park District’s Holiday Express
December 19, 2019 | 4:00pm

It’s time to take a ride to the North Pole! Sign up for your “train ride” from the Family Recreation Center to meet Santa at the North Pole! Activities include crafts, the reading of the Polar Express, bounce house, light refreshments, and more. All persons traveling to the “North Pole” must register. Pre-registration ends Friday, December 14. Please remember to arrive at least 15 minutes prior to your scheduled departure time, there will be a wide range of festive, fun and FREE activities for your family to enjoy while you wait for your trolley.
Register online today!

Snow Much Fun (Westmont)
December 21, 2019 | 4:00 pm – 7:00 pm 
Enjoy free mule-drawn wagon rides around the park, take a photo in the giant snow globe and visit Santa in his workshop. Play games, do crafts, drink hot cocoa, eat s’mores, and more.

November 2020 Family-Friendly Events

We have all kinds of ideas for outdoor fun this winter! Check back regularly for updates to our holiday fun guide throughout the season to simplify your holiday planning, too.

About the Author

Jill Borkowicz
Jill is thrilled to be sharing her insight and knowledge of local fun on Kidlist! As an Oak Park native, Jill and her husband settled in La Grange Park in 2007 and couldn’t be happier with the community they call home. Raising two lovely daughters, ages 8 and 10, Jill is always on the lookout for cool things to do as a family. She is passionate about yummy food, an organized abode, creative entertaining, frugal finds, travel adventures, a healthy spirit, and overall family fun. Jill’s favorite wintertime activity with the fam? Ice skating followed by hot chocolate! Summertime family favorite? Long pool days with friends that end with a BBQ!

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