The Great River Road Experience in Minnesota

• Enjoy a delicious dinner: Dinner at Signatures Restaurant offers groups an elevated dining experience set against sweeping views of Winona’s iconic bluffs.
• Highlights: The gourmet menu highlights locally inspired ingredients, creating a memorable evening that blends regional flavor with an upscale, welcoming atmosphere. As guests dine, they can explore the restaurant’s distinctive collection of signed memorabilia throughout the property—and keep an eye out for a surprise Elvis sighting among the displays.
• Group logistics: Designed with group travel in mind, Signatures offers ample capacity for large groups, supported by multiple private and flexible meeting and dining spaces that can accommodate everything from intimate gatherings to full motorcoach dinners. In warmer months, groups can also take advantage of the outdoor patio and garden areas, providing a scenic extension of the dining experience with bluff views and fresh air.

To round out the evening, groups can enjoy a private mixology class led by knowledgeable and engaging staff, offering a fun, interactive way to connect, unwind, and learn a few signature cocktail techniques before departing.

Explore the heart of downtown Winona with a guided experience led by the Winona County Historical Society through 13 full city blocks listed on the National Register of Historic Places. Preserved architecture, intricate detailing, and rich river city history come together in this walkable district, showcasing Winona’s legacy as one of Minnesota’s most architecturally significant communities.

Along the way, groups will discover historic storefronts, civic buildings, and cultural landmarks, including WNB Financial and Merchants Bank. These architectural treasures feature striking historic design and exceptional stained glass details. Inside WNB Financial, guests can also view a unique collection of antique artifacts—including an original gun collection and African safari trophies belonging to the bank’s early founders—offering a rare glimpse into Winona’s past.

Board the coach for a scenic drive up to Garvin Heights Overlook, where sweeping views reveal the dramatic Mississippi River Valley, limestone bluffs, and the city nestled below. From more than 500 feet above the river, groups can appreciate the unique topography of the Driftless Region, with layered bluff lines, winding waterways, and expansive views creating an unforgettable photo opportunity.

• Enjoy a Unique Museum: Located just off Hwy 61, groups can enjoy a private tour with the owner of Remlinger Collector Car Museum. Jim Remlinger is a passionate local enthusiast who brings the collection to life through stories of the Midwest’s rich drag racing heritage.
• Highlight: Explore one of the region’s finest private collections of vintage drag race cars, along with rare go-karts, antique bicycles, and nostalgic Main Street vignettes that capture a bygone era of American road culture.

• Wellington’s Pub & Grill: Enjoy a relaxed group meal at Wellington’s Pub & Grill, offering a welcoming atmosphere and a menu filled with classic favorites. This local gathering place provides a comfortable stop for groups looking to enjoy great food and conversation before continuing their Winona adventure.

Bloedow Bakery: No visit to Winona is complete without a stop at Bloedow Bakery, a beloved local tradition serving handmade baked goods since 1924. Groups can enjoy freshly made donuts, pastries, and sweet treats while experiencing a true taste of Winona’s community character and hospitality.

Experience the beauty of Winona’s natural landscape from the water with a cruise aboard the Winona Tour Boat. As guests travel along the mighty Mississippi River, Captain Aaron and his co-captain and son River share stories rooted in the history and character of the Upper Mississippi River Valley. Wildlife sightings, including bald eagles, turtles, and beavers, along with a pass by Winona’s unique boathouse community, create a memorable connection to the river culture that defines the region.