I grew up in Red Wing, lived in Winona while attending college for 5 some years, and somehow ended up living back in Red Wing and have been back there for about 14 years now(I also spent a few years living in St. Paul, another lovely river town

). I really like both cities. Winona has a lot to offer as mentioned before. Red Wing really has much the same but fewer dining choices and nightlife options. However, I have to disagree with the comment that Red Wing is cutoff from River by railroad. Actually, I found that Red Wing embraces the Mississippi much more that Winona. A lot of activities focus on the river in Red Wing, including the annual River City Days. Winona focus more on their 2 beautiful lakes and surrounding parks/trails. Either city is a great choice as would be most other cities along the river south of the cities. I think the key is how big a city do you want to live in and how close to major metro areas do you want to be. Red Wing is only 45 minutes from both the twin cities and Rochester. Winona is only 30 minutes from LaCrosse,WI and 45 to Roch. I prefer being close to major metro area so RW.