In 2026, Santa train rides near Milwaukee run Nov 27 through Dec 21, from $18. Happy Holiday Railway at Illinois Railway Museum starts Nov 27, tickets $25–$30. Everyone past their second birthday needs a ticket. Daytime Christmas Trains at East Troy Railroad Museum starts Nov 28, tickets $36–$43. Ages 0–2 need a $13–$16 ticket.
By date
Filter by kind of ride, then tap one for dates, ages, price and how to book.
Santa train · to Dec 21 · Union, IL (7000 Olson Rd) · about 75 miles away28NovSatDaytime Christmas TrainsSanta train · to Dec 20 · East Troy, WI · about 30 miles away28NovSatSanta ExpressSanta train · to Dec 12 · North Freedom, WI · about 105 miles away28NovSatSanta's Special Evening TrainsSanta train · to Dec 19 · East Troy, WI · about 30 miles away28NovSatSanta's Trolley ExpressSanta train · to Dec 20 · South Elgin, IL · about 75 miles away5DecSatHoliday Express Model Train & Flower Show
Model trains · to Jan 3 · Madison, WI · about 70 miles away8DecTueCPKC Holiday Train in SturtevantModel trains · 7–7:30 p.m. · Sturtevant, WI (9900 East Exploration) · about 25 miles away9DecWedCPKC Holiday Train in WauwatosaModel trains · 4:15–4:45 p.m. · Wauwatosa, WI (Harwood Ave railway crossing) · about 7 miles awayNothing matches that filter yet.
What to know
Each line is copied from that operator’s page. When they have not posted a price, the line says so.
Happy Holiday Railway (Nov 27 through Dec 21, Union, IL (7000 Olson Rd) · about 75 miles away). Ages: Everyone past their second birthday needs a ticket. Tickets: $30 adults, $25 kids.
Daytime Christmas Trains (Nov 28 through Dec 20, East Troy, WI · about 30 miles away). Ages: Ages 0–2 need a. Tickets: Adults $41–$43, kids 3–14 $36–$39.
Santa Express (Nov 28 through Dec 12, North Freedom, WI · about 105 miles away). Tickets: $30 adults, $18 children.
Santa's Special Evening Trains (Nov 28 through Dec 19, East Troy, WI · about 30 miles away). Tickets: Adults $69–$79, kids 3–14 $59–$72.
Santa's Trolley Express (Nov 28 through Dec 20, South Elgin, IL · about 75 miles away). Ages: Every passenger needs a ticket, whatever their age. Tickets: $50 per person from Nov 1.
Holiday Express Model Train & Flower Show (Dec 5 through Jan 3, Madison, WI · about 70 miles away). Ages: 5 and under free. Tickets: $10 general, $6 ages 6–12.
CPKC Holiday Train in Sturtevant (Dec 8, Sturtevant, WI (9900 East Exploration) · about 25 miles away). Ages: All ages. Tickets: CPKC's schedule doesn't list a cost.
CPKC Holiday Train in Wauwatosa (Dec 9, Wauwatosa, WI (Harwood Ave railway crossing) · about 7 miles away). Ages: All ages. Tickets: CPKC's schedule doesn't list a cost.
Train rides
Dates, ride length, ages, price and booking notes come from each railroad, zoo or park’s own page. The area line shows where you board.
Quick picks: Cheapest: Santa Express (from $18).
Illinois Railway Museum · Union, IL (7000 Olson Rd) · about 75 miles away
Good to know: A 40-minute ride with Santa on board, cocoa and cookies, and an animated light show. One quiet car skips the show if that suits your kids better.
East Troy Railroad Museum · East Troy, WI · about 30 miles away
Mid-Continent Railway Museum · North Freedom, WI · about 105 miles away
East Troy Railroad Museum · East Troy, WI · about 30 miles away
Fox River Trolley Museum (boards at Blackhawk Station, Jon J. Duerr Forest Preserve) · South Elgin, IL · about 75 miles away
Know one we missed?Send us the railroad’s or venue’s page and we’ll check the dates and add it.Suggest a trainModel trains
Most let you walk through at your own pace, so you can stay as long as little ones are interested.
Olbrich Botanical Gardens · Madison, WI · about 70 miles away
Good to know: Large-scale model trains run among hundreds of poinsettias.
CPKC Holiday Train · Sturtevant, WI (9900 East Exploration) · about 25 miles away
Good to know: The lit-up Holiday Train stops near Racine for a half-hour show with Allen Stone. Wauwatosa gets its stop the next afternoon.
CPKC Holiday Train · Wauwatosa, WI (Harwood Ave railway crossing) · about 7 miles away
Good to know: CPKC's lit-up Holiday Train pulls in for a short trackside show. Allen Stone plays this stop.
More to come.Model train shows often post late. We recheck every week through December.Email me when one’s addedBefore you go
TicketsBook as soon as you canPolar Express and Santa trains often sell out weeks ahead, weekend evenings first.
DressPajamas are part of itMany Polar Express rides invite kids to come in pajamas. Bring a warm layer for the platform.
TimingPick a ride before bedtimeEarly departures are easier with little kids. Late lights trains are better for older kids.Keep planning
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Indoor play in MilwaukeeIndoor playgrounds, toddler times, museums and classes, with prices
Library storytimes in MilwaukeeStorytimes for ages 0–6, by day and branch
Ice skating in MilwaukeeHoliday and indoor rinks, skate aids and prices
Sledding in MilwaukeeSledding hills and snow tubing, with height rules
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Christmas parades in MilwaukeeParades and tree lightings with dates and start timesThe Nutcracker in MilwaukeeBallet and touring shows, sensory-friendly flaggedChristmas markets in MilwaukeeChristkindlmarkts and winter wonderlands with hours
Christmas tree farms in MilwaukeeChoose-and-cut farms, wagon rides and kid notesTree lighting in MilwaukeeDates, times and what the organizer posts for kidsChristmas break in MilwaukeeWhat’s open on Dec 24, Dec 25 and Jan 1
Birthday party places in MilwaukeeStarting prices, ages and what’s included
Youth soccer and T-ball in MilwaukeeSoccer and T-ball for kids under 6, with sign-up dates
More things to do with kids in Milwaukee this weekDated outings for ages 0–6, checked every ThursdayGood questions
Not one we could confirm with 2026 dates on an official page. The closest thing on this page is Happy Holiday Railway, Daytime Christmas Trains and Santa Express.
Happy Holiday Railway (Union, IL (7000 Olson Rd) · about 75 miles away): Next: Fri Nov 27, Sat Nov 28, Sun Nov 29, Sat Dec 5 and 6 more. Daytime Christmas Trains (East Troy, WI · about 30 miles away): Next: Sat Nov 28, Sun Nov 29, Sat Dec 5, Sun Dec 6 and 4 more. Santa Express (North Freedom, WI · about 105 miles away): Next: Sat Nov 28, Sun Nov 29, Sat Dec 5, Sun Dec 6 and 1 more. Santa's Special Evening Trains (East Troy, WI · about 30 miles away): Next: Sat Nov 28, Fri Dec 4, Fri Dec 11, Sat Dec 12 and 2 more. Plus one more on this page.
Holiday Express Model Train & Flower Show at Olbrich Botanical Gardens: Dec 5 – Jan 3, $10 general, $6 ages 6–12. CPKC Holiday Train in Sturtevant at CPKC Holiday Train: Tue Dec 8, CPKC's schedule doesn't list a cost. CPKC Holiday Train in Wauwatosa at CPKC Holiday Train: Wed Dec 9, CPKC's schedule doesn't list a cost.
Many do. One of the eight here asks you to book ahead or warns that seats sell out. Each card says what the operator posts about tickets.
Cheapest ticket: Santa Express, from $18. Those come from the ride length, price and age notes on this page.
Each listing comes from the venue’s or organizer’s own page and links to it. We only list a date, time or price when that page shows it, and anything we can’t confirm stays off. These were last checked Oct 30, 2026, and we recheck them every week through December. How we choose and check.
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