- Exploring the hidden gems of Western Wisconsin—curating unforgettable stays and sharing the places locals love most.
Picture a little brick depot in Osceola, a vintage diesel locomotive rumbling at the platform, and a crowd of kids in sparkly gowns and plastic tiaras bouncing on their toes. The conductor calls “All aboard,” the train lurches forward along the St. Croix, and a few minutes later, two very special guests come walking down the aisle: Elsa and Anna.
That’s the Princess Train, and it’s one of the sweetest family outings in the St. Croix Valley. It’s run by the Osceola & St. Croix Valley Railway, about 50 minutes up the river from Prescott, and the princesses are just the start. There are pizza trains, ice cream trains, fall color trains and a wine tasting train for the grown-ups. Here’s everything I’d tell you before you go.
The railway is operated by volunteers with the Minnesota Transportation Museum, and you can feel how much they love it. The trains leave from the Osceola depot, a handsome brick and brownstone station built in 1916 for the Soo Line. Regular passenger service ended here in 1961, and today the depot is listed on the National Register of Historic Places.
The trains themselves are part of the fun. Depending on the day, you might ride behind a 1950s-era diesel locomotive in restored streamlined coaches from the old Great Northern Railway. Some cars have open rear platforms where you can stand outside and feel the wind as the valley rolls by. Kids love walking between the cars.
South to Marine on St. Croix: about 20 miles round trip and 90 minutes. The train crosses into Minnesota on an 1887 iron bridge and runs through William O’Brien State Park before turning back. You can’t get off at Marine, so just sit back and enjoy the ride.
North to Dresser: about 10 miles round trip and 50 minutes, ending at the historic 1884 Dresser depot. This is the shorter ride, and it’s perfect for little ones.
Elsa and Anna come aboard for a meet-and-greet and photos with every young royal on the train, followed by the 90-minute ride to Marine on St. Croix and back. Dress-up is half the fun, so let them wear the gown. Tickets have been about $43 for adults and about $27 for kids, with babies riding on a lap. It has run on a summer Saturday, and seating is limited. Watch trainride.org and book the moment the 2027 date is posted.
This one is a family favorite. You book a table, and a 16-inch pizza, water and dessert are delivered to you while the train rolls through the valley. Volunteer hosts walk the aisle sharing stories about trains and railroad history. A private table for up to four adults and two small children runs about $171, a table for two about $107, or about $80 if you’re willing to share a table. Beer and wine are sold on board.
Short on time, or traveling with little ones who won’t sit still for 90 minutes? The Ice Cream Train takes the 50-minute run to Dresser, with a free ice cream treat (non-dairy and gluten-free options too). It’s a summer ride and an easy win with toddlers.
In autumn, the Fall Colors Train makes the 90-minute run through the valley at peak color, and peak weekends sell out. The Pumpkin Express pairs the ride to Dresser with an all-day family festival: a free pumpkin for every child, a hayride, food trucks, live music and a flea market.
For the grown-ups, there’s a 21-and-over Wine Tasting Train featuring Wisconsin wines on a 90-minute ride. One note: the wine car isn’t wheelchair accessible.
Before or after your ride, walk down to Cascade Falls, a 25-foot waterfall right in downtown Osceola. About 135 steps lead down to the base, and a trail continues to the St. Croix. Come back after dark and you’ll find the falls lit up with color-changing lights. It’s free and the kids will love it.
For lunch, the Watershed Cafe on Cascade Street serves comfort food made with local ingredients, with a patio over Osceola Creek. It’s open Wednesday through Saturday, 11 a.m. to 8 p.m. Parking downtown is on the street, or you can leave the car at the depot.
Want to keep going? St. Croix Falls is just 15 minutes north, where Interstate State Park has trails above the river and giant glacial potholes the kids can peer into.
Make downtown Prescott your home base and book direct with us: The Port of Prescott for boutique king suites steps from the river, Port After Dark for romantic suites made for couples, The Harbor Hotel for themed rooms and extended stays, and The Cove Guest House for downtown condos and group getaways.
