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Wisconsin's Pumpkin Train Rides

Published: August 26, 2025

By: Adam Burns

When the maples flame and the air turns crisp, Wisconsin’s heritage railroads roll out one of the season’s most charming traditions: pumpkin train rides.

Equal parts nostalgia and harvest celebration, these excursions mix the rhythm of steel wheels with family-friendly stops to pick pumpkins, sip cider, and soak up fall color.

Whether you’re traveling with little ones or simply chasing autumn magic, here’s a detailed look at where and how to ride a pumpkin train in Wisconsin, what to expect, and tips to make your outing smooth and memorable.

National Railroad Museum

The Great Pumpkin Train

One of the state’s best-known October traditions, the National Railroad Museum’s Great Pumpkin Train typically runs over select days in mid to late October. The experience blends a short, scenic ride on the museum’s grounds with an on-site pumpkin patch, so even the youngest riders can enjoy the novelty without a long day of travel.

While details vary by year, the event usually features timed departures, seasonal storytelling or activities inside the museum, and the chance for each child to select a pumpkin. The museum’s sprawling indoor exhibits make this a strong choice if the forecast is iffy; you can explore classic locomotives and rolling stock before or after your ride, making the outing more than just a quick trip.

Mid-Continent Railway Museum

Pumpkin Special

Nestled in Sauk County’s rolling Baraboo Hills, the Mid-Continent Railway Museum typically schedules a Pumpkin Special alongside its regular autumn excursions.

The museum’s restored coaches carry you through oak and maple forest on a roughly hour-long journey, traveling a total of 7 miles, that highlights the area’s color. For the pumpkin-themed trips, families ride out to Quartzite Lake where a local farmer offers pumpkins for sale.

Equipment and motive power can vary by season but visitors can always expect to enjoy a ride within either a beautifully restored coach or caboose. Regardless, the museum setting—complete with a classic depot and period freight cars—makes for an atmospheric fall day.

Riverside & Great Northern Railway

Pumpkin Express

For young children, the Riverside & Great Northern Railway in Wisconsin Dells is magical. This is a 15-inch gauge, live steam railroad set in the woods just minutes from the Dells’ main drag.

The smaller scale puts kids close to the action: you can watch the crew tend the engine, hear the chuff of the cylinders, and feel the warm breath of steam on a chilly morning.

During its Pumpkin Express, which are typically scheduled on select October days, the railroad states kids under 12 can pick out a pumpkin for free! Because seating is limited and the event is popular, early arrival or advance ticketing is recommended.

Osceola & St. Croix Valley Railway

Pumpkin Express

Operated by the Minnesota Transportation Museum, the Osceola & St. Croix Valley trains trace the bluffs along the wild and scenic St. Croix River. In addition to regular fall color runs, the schedule often includes a Pumpkin Express or similar themed trip in October.

These have historically included a stop where children can choose a pumpkin, along with leaf-peeping views that can be spectacular at peak.

The trip runs 25 minutes out to Dresser where the kids can pick out their favorite pumpkin before returning.  The event also includes music, games, hayrides, treats, and even a small flea market. Because fall is their busiest season, reserve early and build in extra time for parking and boarding.

Planning Tips

Book early: Pumpkin trains are among each railroad’s most popular events. As soon as dates are announced—often late summer—grab your preferred time slot.

Dress for the weather: Platforms, pumpkin patches, and open-window coaches can feel chilly. Layer up, wear closed-toe shoes for uneven ground, and bring gloves when in doubt.

Time your foliage: In northern Wisconsin, peak color often arrives late September to early October; farther south, it can be mid to late October. If color is a top priority, consult regional fall color reports and aim for midweek or morning departures for better light and fewer crowds.

Build in buffer time: Arrive 30–45 minutes before departure for parking, ticket pickup, and boarding. Many depots have small exhibits or gift shops worth a quick browse.

Have a rain plan: Some railroads run rain or shine; others may adjust operations. Events with museum components (like Green Bay’s National Railroad Museum) offer more indoor fallback options.

Choosing the right pumpkin train for your crew
- For toddlers and short attention spans: Riverside & Great Northern’s brief, intimate steam rides or the National Railroad Museum’s short loop plus indoor exhibits keep the day manageable.
- For maximum fall flavor: East Troy’s ride to The Elegant Farmer or Osceola’s bluff-hugging St. Croix Valley trips combine foliage, fresh air, and seasonal treats.
- For railfans: Mid-Continent’s historic coaches, Osceola’s classic consist, or Laona’s steam heritage deliver strong railroad ambiance alongside the pumpkin fun.

Schedules and Accuracy

These seasonal excursions can change year to year based on staffing, equipment availability, and weather. Some operations may pause or rebrand special events, and inclusions like “one pumpkin per child” can vary. Before you finalize plans, check the official websites or call the railroad or museum to confirm dates, departure times, accessibility details, and what your ticket includes.

Final Thoughts

As pumpkins pile into laps and canvas totes, and the conductor’s call echoes down the platform, you’ll understand the enduring appeal of these outings.

A pumpkin train ride isn’t just transportation to a patch—it’s a rolling slice of fall tradition, a way to slow down and savor color, community, and the gentle clatter of history on the rails. If you can, make it a yearly ritual. The pumpkins change, the kids grow, the leaves turn anew, and the memories only get better with time.