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

Outdoor ActivitiesWinter

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!

2021 Old-Fashioned Carriage and Holiday Trolley Rides

Long Grove Vintage Holidays (Long Grove)
November 20, 2021 – December 19, 2021 (every weekend between these dates)
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. Holiday caroling and a visit from Santa on select weekends, too!

Holiday Lights Tours (Naperville)
November 26 – 28, 2021 and December 1-27, 2021 (closed on Christmas) | 5:00 pm – 10:30 pm 
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.

Christmas Walk & Holiday Market (Clarendon Hills)
December 3, 2021| 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 6:30 pm. Grinch and Scrooge photo opportunities, too.

Holiday Lights (Homewood)
December 3, 2021 | 5:00 pm – 9:00 pm 
Enjoy the most wonderful time of the year upon a musical trolley that travels to all the unique stores and dining establishments around town. Costumed characters and carolers, an antique car show, ice sculpting demos, a bonfire, hot cocoa, music, and more.

Festival of Lights (Bloomingdale)
December 3, 2021 – January 1, 2022
The annual Festival of Lights will be brighter than ever this year with picturesque horse-drawn carriage rides (registration required). Enjoy holiday crafts, cookie decorating, refreshments and a visit with Santa. A replica of the classic Walnut Room Christmas tree will be displayed at the museum, and there will be photo ops, too.

The Santa Trolley (Oak Park)
December 5, 2021 | 10:15 am – 11:45 am
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.

Holly Jolly Trolley (Westmont)
December 11, 2021 | 12:00 pm – 6:00 pm
All aboard the Holly Jolly Trolley will have the chance to make cookies with Mrs. Claus, listen to holiday stories, and make an ornament as a keepsake of this wintry ride around Westmont. Family pricing varies depending on the size of your group, register in advance.

Holidays in Hinsdale
December 11 and 18, 2021 | 11:00 am – 2:00 pm
Enjoy horse drawn carriage rides, boutique and holiday shopping, gingerbread cookies, and visit Santa Claus at Burlington Park.

Holiday Trolley Express (Prospect Heights)
December 16 – 17, 2021 | 4:30 pm – 8:30 pm 
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.

Check out all the cool ideas and inspiration for the most outdoor 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 2021 Polar Express Train Rides!

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