Greater Milwaukee sleigh rides: Your winter 2025 guide

The greater Milwaukee area offers sleigh ride venues for winter, ranging from intimate horse-drawn farm experiences to a 43-person "giant sleigh" through millions of holiday lights. Most traditional sleigh rides require 4-6 inches of snow—without it, venues offer wagon rides instead. Reservations are required everywhere, and holiday dates like Christmas Eve and New Year's Eve book months in advance. Prices range from $5 per person for downtown carriage rides to $135+ for private farm experiences with campfires and s'mores.

Apple Holler delivers the winter farm experience

Location: 5006 South Sylvania Avenue, Sturtevant, WI 53177 (Racine County)

Apple Holler's sleigh rides consistently rank among Wisconsin's best—USA Today named it a top family destination in Racine. Haflinger horses pull guests through a 78-acre snow-covered orchard and "Enchanted Forest" featuring 100+ year-old hardwood trees.

What's included: The $135 base price (for up to 4 people) covers a 20-minute private sleigh ride, a private campfire reserved for 30-45 minutes afterward, s'mores fixings, your choice of hot chocolate or apple cider, and access to a heated dome for warming up. Additional guests cost $30 per person (tax not included), and sleighs comfortably seat up to 10 people. Groups larger than 10 split across multiple sleighs.

Reservations: Phone-only through coordinator Elyse at (262) 884-7100. Book up to one year in advance—critical for Christmas Eve, New Year's Eve, and New Year's Day, which fill quickly. Minimum 48-hour advance booking required. No refunds, but rescheduling within the same season is possible. If snow never materializes, rides convert to wagon rides.

Accessibility: The campfire area is wheelchair accessible. Two small steps to board the sleigh/wagon.

Pro tips: Bring your own blankets for extra coziness and long carrots to feed the horses after your ride. Combine with breakfast or lunch at the on-site Red Barn Restaurant.

Website: appleholler.com/sleigh-rides

Roden Barnyard Adventures

Location: 5545 County Road Y, West Bend, WI 53095 (Washington County)

This working 850-cow dairy farm transforms into a winter wonderland with thousands of Christmas lights illuminating woodland trails. Percheron horses Wilbur and Clyde pull an old-fashioned sleigh seating up to 12 adults.

Pricing: Adults pay $49, children ages 3-13 pay $29, and kids under 3 ride free. Want a private ride? Purchase all 12 tickets.

Confirmed December 2025 dates:

• December 6, 12-13, 19-20, 22-23, 26-27

• January 2-3, 2026

• Closed December 24-25

What's included: A 25-minute ride through lit woods, 5 minutes to meet the horses, campfire access before and after your ride, and a heated building with board games. Hot apple cider and hot chocolate available for purchase. Guests may bring their own food and beverages (except outside cocoa, cider, or popcorn).

Reservations: Book online via FareHarbor at rodenbarnyard.com. Arrive 20-30 minutes early—sleighs depart exactly on schedule with no waiting. Tickets are non-refundable but transferable. For groups of 25+, call (262) 689-7521 for private ride dates.

Weather policy: Rides are not cancelled for lack of snow—wagon rides substitute. Cancellations only occur for lightning, freezing rain, or temperatures below 10°F (notification 3 hours prior).

Website: rodenbarnyard.com/sleigh-rides

Hoof Beats Express

Location: W359N9054 Brown Street, Oconomowoc, WI 53066 (Waukesha County)

This family-owned farm features a collection of antique sleighs and stately dapple gray and white Percheron draft horses. The 116-acre property offers genuine "old Wisconsin winter" atmosphere.

Three sleigh options:

• Minnesota Country Sleigh: Standard group sleigh

• Large Bobsled: Up to 12 passengers (minimum 6 required)

• Antique Canadian Cutter: Private two-person romantic ride, $45/person

Standard pricing: Adults $35, children 5-11 $15, under 5 free.

What's included: 35-40 minute ride, hot chocolate and cookies afterward, warmed barn with carriage collection viewing, and warm blankets.

Reservations: By appointment only, 7 days a week. Call (262) 853-9801. Snow conditions must support sleigh operation.

Accessibility: Wheelchair-accessible wagon available upon request.

Website: hoofbeatsexpress.com

Kettle Moraine Carriages

Location: N612 Forest View Road, Kewaskum, WI 53040 (Washington County)

With 40+ years of operation, this family business offers intimate sleigh rides through a 65-acre property in the Northern Kettle Moraine—one-third wooded, two-thirds open fields. Belgian or Percheron draft horses pull sleighs seating 6-8 people.

Pricing: $100 per hour per sleigh—one of the best values for groups wanting extended private rides.

What's available: Warming house rental (additional hourly fee), bonfire setup (additional fee). Guests bring their own blankets and beverages.

Reservations: By appointment only, 7 days a week. Requires 2-4 inches of snow for sleigh operation. Call (262) 626-4883.

Best for: Romantic couples rides or families wanting unhurried, private experiences without crowds.

Website: kettlemorainecarriages.com

Dan Patch Stables

Location: 7036 Grand Geneva Way, Lake Geneva, WI 53147 (Walworth County)

Located at the entrance to the Grand Geneva Resort, Dan Patch Stables has offered horse-drawn transportation since 2002. Sleigh rides traverse hundreds of acres of resort property including snow-covered fields and wooded areas.

Pricing: Call for current sleigh ride rates. Cash only (resort guests can charge to room).

Hours: Weekdays 10am-4pm, weekends 9am-5pm for general operations. Sleigh rides require advance scheduling.

Reservations: Call at least 24 hours in advance at (262) 215-5303. Requires 6-8 inches of snow; wagon/carriage rides offered otherwise.

Bonus amenities: Free petting zoo with goats, cows, chickens, pigs, and donkey. Pony rides for children 6 and under. Bonfires available with advance notice.

Best for: Families combining a sleigh ride with a Grand Geneva resort getaway or Lake Geneva day trip.

Website: danpatchstables.com

Wisconsin Christmas Carnival of Lights

Location: 8425 Highway 38, Caledonia, WI 53108 (sleigh boarding at 10006 7 Mile Road)

This is not a traditional horse-drawn experience but something entirely different: a motorized 43-passenger sleigh with tiered seating traveling through 3+ million holiday lights—the Midwest's largest drive-through light show.

Season: November 22, 2025 through January 31, 2026

December 2025 hours:

• December 1-11: Sunday-Thursday 5pm-9:30pm, Friday-Saturday 5pm-10pm

• December 12-20: Sunday-Thursday 5pm-9pm, Friday-Saturday 5pm-10:30pm

• December 21-24: 5pm-10pm (Christmas Eve closes 9pm)

• December 26-31: Daily 5pm-9pm

Options: Santa's Giant Sleigh (43 seats, tiered), premium seating upgrades, Sunday "Santa Sleigh Rides" with Santa photo opportunities, and Golf Cart Holiday Train rentals (up to 8 people, max 4 adults).

Pricing: Variable by date and seat type—book online. Children 2 and under free as lap riders.

Reservations: Book online at wichristmascarnival.com at least 7 days in advance recommended. Tickets non-refundable. For large groups, call (262) 835-2565.

What else: Candy Village activities, Santa's Workshop, outdoor ice skating, Breakfast with Santa (December weekends), hot cocoa and bourbon flights.

Best for: Families wanting holiday spectacle rather than traditional farm sleigh experience.

Website: wichristmascarnival.com

Downtown holiday carriage

Two downtown areas offer affordable urban carriage experiences through decorated streets during December 2025:

Downtown Waukesha Holiday Carriage Rides

Boarding: Realty Executives Southeast, 431 W Main Street, Waukesha
December 2025 dates: Saturdays December 7, 14, and 21 from 12pm-4pm
Price: $5 per person
Contact: downtownwaukesha.com (part of Silver Bells celebration)

Oconomowoc Carriages with the Clauses

Location: Downtown Oconomowoc
December 2025 dates: Thursday-Sunday, December 11-14
Price: $100 per ride (up to 10 passengers, max 6 adults)
Duration: 15-minute time slots
Includes: Hot chocolate bar, reindeer food activity, Santa and Mrs. Claus photo opportunity
Reservations: Required through oconomowoc.org. Non-refundable.

Country Christmas wagon rides

Location: The Country Christmas, Waukesha County
December 2025 dates: November 30-December 2, December 4, December 7-11, December 14-18
Times: 5:15pm, 6pm, 6:45pm, 7:30pm, 8:15pm
Price: $20 per person (includes hot chocolate and cookie)
Contact: thecountrychristmas.com

Note: These are wagon rides through their light display, not traditional sleigh rides, but included for families seeking similar experiences.

Quick comparison for planning

Venue Price Capacity Duration Key Feature Apple Holler $135 base + $30/extra 10 1 hour total Private campfire, heated dome, s'mores Roden Barnyard $29-$49/person 12 25-30 min Christmas lights, working dairy farm Hoof Beats Express $15-$45/person 2-12 35-40 min Antique sleigh collection Kettle Moraine $100/hour 6-8 1 hour Best value for private groups Dan Patch Stables Call for rates Varies Varies Grand Geneva Resort access Christmas Carnival Per ticket online 43 20-45 min 3+ million lights Downtown Waukesha $5/person Varies Short Budget-friendly urban ride Oconomowoc Clauses $100/ride 10 15 min Santa photos, hot cocoa

Essential planning tips

Book early for holidays: Christmas Eve, New Year's Eve, and the week between Christmas and New Year's fill fastest. Apple Holler accepts bookings up to one year in advance.

Weather contingencies: All horse-drawn sleigh venues require adequate snow (typically 4-6 inches). Most offer wagon rides as alternatives—your experience continues regardless. Only the Christmas Carnival's motorized sleigh operates in all conditions.

What to bring: Warm layered clothing, your own blankets (most venues encourage this), and cash for Dan Patch Stables. Apple Holler guests can bring carrots for the horses.

Cancellation reality: Most venues offer no refunds—tickets are transferable to other people. Weather cancellations (extreme cold, ice storms) are rare but result in refunds or rescheduling.

Confirmation calls: December 2025 schedules and pricing may adjust. Call venues 1-2 weeks before your planned date to confirm operations and availability.