Sugar Loaf is an iconic place in Winona, MN. It is lit up at night all year round so you can see it for miles. It can be crowded some days but this is mostly due to local foot traffic. Most people that go up to Sugar Loaf are not there to climb.
At the intersection of Mankato Ave and Highway 61 in Winona, head south on 43 to a quick right hand turn to E Lake Blvd to a quick left on Sugar Loaf Road, next take a left on W Burns Valley Road, go past fire hydrant on the right side of the road and there are steps that lead to a water tank. Go up around the water tank on the right hand side. There is one approach that goes straight up a class 4 scramble or 30 feet past that is the easier approach which is a trail leading to the top.
Mountain Project's determination of some of the classic, most popular, highest rated routes for Winona, Sugar Loaf:
There are 5 sets of bolted anchors and 2 lead routes (3 if you decide to link up from right to left). Routes range from 5.4-5.9 depending how you choose to climb them. The climbing here is not the best quality if you are an experienced climber looking to sport climb. Nonetheless if you are new to climbing and looking to experience top rope climbing outside this is a great destination, and the view is spectacular.
The 3 left most anchors can be easily free soloed (5.4ish) by an experienced climber to set TRs. The right 2 anchors can be lead or you can scramble up the backside (fith class)to set TRs.
The Winona State University Outdoor Education & Recreation Center makes regular use of the sugar loaf during the school year.