6 most magical sleigh and carriage rides near Chicago

If you really want to make a holiday memory, bundle up the family and delight in the old-fashioned fun of a horse-drawn sleigh ride. With the amount of snow we are predicted to get this winter, you’ll have the perfect backdrop (and ground cover) for a sleigh ride, caroling optional.

Apple Holler

Apple Holler offers horse drawn sleigh rides through its beautiful orchard that ends with a cup of hot chocolate or warm apple cider. No snow? You can do a horse-drawn wagon ride instead. Sleigh rides are 30 minutes long through the wooded wonderland, and you can also have s’mores and drinks around a campfire at the end. Rides are $80 for four people and $15 for each additional person. Reservations are required in advance. Feel free to bring a blanket to stay cozy or carrots for the horses.

5006 S. Sylvania Ave., Sturtevant, Wis.

Dan Patch Stables

The horse-drawn sleigh rides located in Lake Geneva are calling your name. Sit back and relax as the horse-drawn sleigh ride takes you through some of the most beautiful areas on the Grand Geneva property. Make sure to call to reserve in advance and check availability. Rides are $60 per sleigh. If you’re visiting the area during the evening, make sure to check out Grand Geneva’s drive-through light show.

7036 Grand Geneva Way, Lake Geneva, Wis.

Mansell Homestead

Located just 40 minutes from The Loop, this serene homestead turns into a winter wonderland when it snows. The horse-drawn sleigh can seat up to three and will take you through rural roads and natural beauty. Sleigh rides are private, require reservations, are 40-45 minutes long and cost $140.


Forest View Farms

This Tinley Park family-owned business has been providing family-friendly horse fun since the 1950s. Sleigh rides are available for groups for $7-$10 per person. Two-passenger rides are available for $50. Call to check availability and schedule a ride.

16717 Lockwood Ave., Tinley Park

Historic Downtown Long Grove

Every Saturday and Sunday in December, experience Vintage Holidays at historic downtown Long Grove starting with complimentary horse-drawn carriage rides. Rides are free and are on a first-come, first-served basis, but you must sign up in person at the Visitors Center. After your ride, stroll down the cobblestone streets, listen to strolling costumed carolers and musicians, or shop or dine at the small family-owned shops and restaurants that line this cute little downtown.

308 Old McHenry Road, Long Grove

Ben’s Christmas Tree Farm

If you’re looking to cut your own tree AND take in a carriage ride, head on over to this Harvard tree farm where customers can enjoy a horse-drawn wagon ride. Hurry though, this weekend (Dec. 7-8) is their last weekend they are offering rides.

 7719 Ryan Road, Harvard

Skip the horses, I just need a sleigh (and Santa)

If all you want is an adorable picture of your kids bundled in a historic sleigh while the snow swirls around them, head to Cook Park in Libertyville. A gorgeous vintage sleigh is set up for the perfect photo op in front of the historic Cook Mansion during Dickens of a Holiday for pictures with Santa on Dec. 7 and 14.

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Chicago Parent Editorial Team
Chicago Parent Editorial Team
Since 1984, the Chicago Parent editorial team is trained to be the go-to source for Chicagoland families, offering a rich blend of expert advice, compelling stories, and the top local activities for kids. Renowned for their award-winning content, the team of editors and writers are dedicated to enriching family life by connecting parents with the finest resources and experiences our community has to offer.
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