Winona is a lively, scenic Mississippi River college town with a compact historic downtown, a strong arts and music scene, cozy cafés, breweries and farm‑to‑table restaurants — great for multi‑week stays with easy access to bluff hikes, biking, kayaking and seasonal festivals.
Within an easy drive are La Crosse, WI (~30 miles) for a bigger riverfront nightlife and outdoor scene, and Rochester, MN (~55 miles) for expanded dining, shopping and entertainment options.