Looking for a cozy winter adventure?
Just a short drive from Milwaukee, you’ll find enchanting sleigh rides that are perfect for soaking up the holiday spirit. Picture snow-covered trails, twinkling lights, and the gentle jingle of sleigh bells as you’re pulled through scenic woodlands and festive farms.
Bundle up, bring your loved ones, and get ready for a magical sleigh ride experience at one of these charming spots around Milwaukee!
1. Apple Holler
5006 S. Sylvania Ave., Sturtevant, WI 53177
Website
The old-fashioned private sleigh rides at Apple Holler take you and your family on a private tour of the snow-covered orchards and 100-year-old hardwoods, while you enjoy the scenery and listen to the clopping of the Amish Haflinger horses pulling you (reservations required).
Afterward, enjoy s’mores around a campfire and a cup of hot cocoa or warm apple cider. Apple Holler recommends wearing warm clothes and bringing your own comfy blankets. Want to tip your horses? Bring some long carrots for them to snack on!
2. Roden Barnyard Adventures
5545 County Road Y, West Bend, WI 53095
Website
Listen to the sleigh bells ring while a team of Percheron horses pull you on a sleigh across hundreds of beautiful wooded acres lit with thousands of Christmas lights. (If there’s no snow on the ground, the team will pull a wagon ride.)
Before your ride and after, sit at the campfire and tell stories – or warm up inside the heated building with a cup of hot apple cider or hot chocolate. Spend some time visiting with friends while you play an old-fashioned board game.
Guests are welcome to bring food and other beverages while enjoying a night with family and friends. The old-fashioned sleighs hold up to 12 people. Reservations are required.
3. Wisconsin Christmas Carnival of Lights
Jellystone Park, 8425 Hwy 38, Caledonia, WI 53108
Website
Jellystone Park Camp-Resort in Caledonia offers sleigh rides so you can enjoy their Wisconsin Christmas Carnival of Lights in open air. Santa’s Giant Sleigh seats 43 guests in tiered and comfortable seating (select a “premium” seat for a more spectacular experience).
On Sundays, you can ride with the man in red himself during a Santa Sleigh Ride! This ticket includes a free sticker, plus an opportunity to take your own photo with Santa!
4. Hoof Beats Express
W359N9054 Brown St., Oconomowoc, WI 53066
Website
Enjoy a 40-minute ride on this 116-acre farm (snow permitting). There are three sleighs to choose from: an antique Minnesota country sleigh, a large bobsled, and a very special antique Canadian cutter built for two ($45 per rider).
The largest sleigh carries 12 passengers with a minimum booking of 6 riders. Check out the small carriage collection in the warmed barn before or after your ride.
Kettle Moraine Carriages
N612 Forest View Rd., Kewaskum, WI 53040
Website
Hear the bells jingle and see the scenic fields and forest on the Schulz’s 65-acre farm during this one-hour ride. Horse-drawn sleighs hold up to 6 people and operate 7 days a week by appointment only.
Dress warmly and bring along your own warm blankets, as well as snacks or drinks of your liking. There’s a warming house for rent by the hour, or you can order a bonfire for an addtional fee. The sleighs require 2-4 inches of snow; wagon or carriage rides are given in the absence of snow.
Dan Patch Stables
7036 Grand Geneva Way, Lake Geneva, WI, United States, 53147
Website
The horse-drawn sleigh rides at Dan Patch Stables take you through some of the most beautiful areas on the Grand Geneva property. Sleigh rides are weather and snow-condition permitting, so call before you go. (A good base layer of 4-6 inches of snow is required.)
Horse Drawn Carriage Rides in Waukesha
Experience the charm of holiday carriage rides in Downtown Waukesha this December!
Dates & Times:
- Saturday, December 7, 12:00 – 4:00 PM
- Saturday, December 14, 12:00 – 4:00 PM
- Saturday, December 21, 12:00 – 4:00 PM
Tickets:
- $5 per person
- Purchase tickets and board the carriage at Realty Executives Southeast (431 W Main St).
Note: Rides are weather permitting.
There’s more!
Holiday Light Displays
Santa’s Mailboxes
Magical Holiday Experiences
Local Toy Stores
Where to Meet Santa
Calie Herbst, Editor-in-Chief of Milwaukee With Kids, has spent over a decade combining her experiences as a parent of three to create a hub for Milwaukee’s family adventures.
Her decade-long teaching career in Milwaukee Public Schools and academic background, including a Master’s in Teaching from Marquette University and dual B.A.s in Sociology and Spanish from the University of Wisconsin – Madison, fuel her passion for inclusive and engaging family content.
Calie is also a recognized voice in local media, contributing to WISN Channel 12 News, WTMJ Wisconsin Morning News, Fox 6’s Real Milwaukee, and B93.3.
Discover more about Calie’s journey and editorial approach on her About Page and Editorial Policy Page.
