Set along the St. Croix River in northwest Wisconsin, Osceola offers couples a setting that feels both scenic and deeply personal. This historic river town is a favorite for romantic getaways, anniversary weekends, and intimate elopements, especially for those who enjoy nature, walkable downtowns, and a sense of discovery. With its waterfront location and a downtown listed on the National Register of Historic Places, Osceola delivers an experience that feels authentic and easy to enjoy together.
There are plenty of things to do in Osceola. One of the town’s most memorable features is Cascade Falls, a dramatic twenty-five-foot waterfall located just steps from Main Street. From there, wooded trails wind through Wilke Glen, creating a peaceful path that feels tucked away despite its proximity to downtown. Osceola’s historic district invites slow wandering, with antique shops, art galleries, and locally owned boutiques housed in beautifully preserved nineteenth-century storefronts.
A highlight for many visitors is the Osceola and St. Croix Valley Railway. Departing from the restored 1916 Soo Line depot, this scenic train ride follows the river and the surrounding countryside, offering a nostalgic way to experience the landscape together. It is an especially popular choice for couples who enjoy travel experiences that feel relaxed and immersive rather than rushed.
Food and drink experiences extend just beyond town as well. Many couples make time for a visit to Chateau St. Croix Winery in nearby St. Croix Falls, where tastings take place at a European-inspired estate surrounded by formal gardens. Wines like Thoroughbred Red and La Crescent White are favorites for lingering afternoons. Craft beer fans often head to Trap Rock Brewing, known for approachable pours like Whitetail Ale enjoyed in a relaxed setting.
For a great meal, head to The Watershed Cafe, a local restaurant well known for farm-focused comfort food paired with views overlooking the falls. Tippy Canoes is a local favorite for burgers and hearty entrées that feel satisfying after a day outdoors. But, really, the true star of any getaway to Osceola is a stay at one of our charming bed and Breakfasts. Wherever you stay, this river town offers scenery, history, and a pace that encourages couples to slow down and enjoy time together.