Nestled into rugged bluffs of the St. Croix River, the quaint village of Osceola, Wis., has stayed true to its historical roots while managing to tickle the fancy of outdoor enthusiasts, train lovers and those in search of a good farm-to-table meal.

An hour’s drive from the Twin Cities, the village is just across the state line in an area that some call “Minnesconsin.”

Settled in 1844, at a time when steamboats chugged up and down the river and fur traders hustled their wares, Osceola grew up around the beautiful Cascade Falls, which remains the crown jewel in the center of town.

Welcome to … LeRoy?

The first recorded name for this once-burgeoning river town was LeRoy, a move meant to honor “the first white man” to die there, according to records from 1853. LeRoy (whose last name was either Hubbard or Hauble) was a lumberjack who met his untimely death while building the saw mill. The name, however, didn’t stick. Around 1900, after trying a few other names, the town officially became Osceola. While it might seem strange that a river community in Wisconsin was named after a Florida Seminole who never set foot in the place, the village is in good company: Osceola has more places in the country named after him than any other American Indian.

Falls in town

To experience the power of Cascade Falls, all you need to do is descend the stairway at the center of town. (You can’t miss it. It’s right next to the wooden Osceola statue.) Venturing to the 25-foot waterfall is a reward all its own. Picnickers often spread out around the soggy lowland and children squeal and splash in the pooled waters. But be forewarned: Getting back to street level from Cascade Falls requires an ascent of 135 stairs.

Take a hike

From Cascade Falls, hearty walkers can push onto a 1-mile loop that leads to Eagle Bluff Trail, which offers expansive views of the canopied river valley. The hike is one of 11 established “rivertown trails” that wind through river bluffs, historic sites and flowing streams. Many of the trails, which are described in the town’s brochure as “uplifting” or “vigorous,” are open in winter to cross-country skiers and snowshoers.

Other popular trails include the 98-mile Gandy Dancer State Trail, a hard-surface trail for hiking and biking, about 7 miles north on Hwy. 35, and the Ice Age National Scenic Trail (, a 1,000-mile footpath with landscape formed by glaciers.

All aboard

If you want to cover more ground, the Osceola & St. Croix Valley Railway is a popular way to see the countryside. The rides, available on weekends through October, head to Marine on St. Croix (90 minutes) or Dresser (50 minutes). There are brunch trains, pizza trains and dinner trains as well as special trips (think pumpkin patch in fall). Tickets vary, generally ranging from $25 to $55. (1-715-755-3570).

The train leaves from the historic railroad depot, which is worth a visit on its own (

Dine and shop

A stroll along Mainstreet (aka Cascade Street), where some buildings date to the 1880s, offers great riverfront views, interesting shopping and a variety of eating options. Established venues such as Py’s ( remain a favorite of motorcyclists and burger-lovers, as does Osceola Lanes ( where you can get a $3 breakfast (two eggs and toast) served at a table fashioned out of old bowling lanes.

The newcomer, Watershed Cafe (, 1-715-294-2638), offers farm-to-table breakfast, lunch and dinner and boasts a deck that overlooks a small park above Cascade Falls.

Savor a Wisconsin-crafted ice cream cone while shopping for antiques and repurposed creations at the Looking Glass (1-715-294-2886). The finds are clever, but don’t expect bargains. You might have better luck at the thrift store up the street.

Zip in for a thrill

Check your nerves at the door of the Adventures Park, a high-wire challenge course and zip line park at Trollhaugen Outdoor Recreation Area (, 1-715-755-2955) in nearby Dresser. The 90-minute zip line tour slices through the treetops and over a pond to deliver spectacular views and enough speed for thrill-seekers. The opening run is a mild 12 miles per hour, while the fastest run averages a zippy 35 mph. Be braced for the final run, which requires you to muster the courage to leap off a 60-foot-high platform. A basic tour costs $45 for adults, $39 for students.

California on the St. Croix

Ease down from the day at the Dancing Dragonfly Winery ( The 60-acre facility and event center makes all of its wines on-site, with grapes sourced primarily in Wisconsin and Minnesota. It offers tours and tastings as well as handcrafted pizza and gourmet deli meats and cheeses. Sit on the back deck for a view of climbing grapevines. A tasting of five wines plus a glass costs $10. Tours cost $15.