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Looking for a unique outing with the kids? Horse-drawn carriage rides are a cozy, memorable way to experience Wisconsin’s history, scenery, and seasonal magic. While options are limited in the Milwaukee area, there are still a few wonderful places where families can enjoy a carriage, wagon, or sleigh ride throughout the year.
Here are the top spots to explore:
💡 Looking for more ideas? Explore our favorite family outdoor activities across Wisconsin →
1. Wade House — Greenbush, WI (Wisconsin Historical Society)
Best for: history-loving families, hands-on experiences, day trips
Season: Spring–Fall, with special seasonal weekends
Just over an hour north of Milwaukee, the Wade House brings the 1850s to life with horse-drawn rides, living-history exhibits, and hands-on demonstrations. Families can hop aboard a horse-drawn carriage or tram (depending on the weekend) and ride back to a working sawmill, blacksmith shop, and historic inn.
Inside the inn, you’ll tour the living quarters, hotel rooms, and kitchen — complete with freshly baked cookies and a chance for kids to help prep the next batch. Special weekend programming often includes feeding animals, making fire starters, and other simple activities.
Plan for 3–4 hours and consider pairing your visit with other nearby stops.
💡More ideas: See our full list of Best Day Trips From Milwaukee →
2. Old World Wisconsin — Eagle, WI
Best for: immersive history, traditional wagons, seasonal programming
Season: Summer + special fall/winter events
Old World Wisconsin offers historic wagon rides during select events and weekends. These rides vary year to year, but typically include horse-drawn wagons as part of themed programs or immersive living-history days. It’s a great option for families who want a ride woven into a full outdoor experience—think historic crafts, hands-on demonstrations, and wide-open trails.
Check their calendar each season to see when rides are available.
💡Want a closer look before you go? Read our full review of Old World Wisconsin →
3. Hoof Beats Express — Oconomowoc, WI
Best for: classic carriage rides, small-group experiences, winter outings
Season: Year-round with winter rides on wooded trails
Hoof Beats Express offers traditional horse-drawn carriage rides led by their stately Percheron draft horses. Families can book private rides, attend seasonal programming, or sign up for their popular Winter Rides on the Farm, which follow a wooded trail and make for a peaceful cold-weather outing.
Typical Winter Ride Details (may vary by year):
- Dates often fall around late December
- Ride length: approx. 45 minutes
- Group size: minimum 4 riders, maximum 12
- Pricing usually around:
- Adults: ~$35 per rider
- Youth (10 and under): ~$20
- Ages 3 and under: free
Because offerings and dates shift seasonally, it’s best to check their schedule each year.
4. Seasonal Sleigh Rides (Weather-Dependent)
Wisconsin weather doesn’t always cooperate, but when it does, sleigh rides become one of the most magical winter activities. Several farms and stables across Southeastern Wisconsin occasionally offer sleigh rides when the snow is deep enough.
💡Explore more options: See our Full Guide to Sleigh Rides in Wisconsin →
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.
