This is a beautiful little town that has a yearly Apple Fest that is HUGE and a lot of fun. Of course they have apple everything (cidar, meals, caramel apples, pastries, pies) along with an arts and crafts show, live bands, carnival, wine tasting and food galore. I've never had an apple wine before, and it's really pretty good! It's one of the best small town festivals in the U.S. and the town just swells with people.
The town has a harbor and is a big sail boating mecca. Every Friday the harbor will have a Parade of Lights where the boat owners will decorate their boats and then drive them close to the shore for the audience to judge and see how pretty they look. There are even ice caves that I would LOVE to be able to see sometime in the winter, they look gorgeous and you can kayak or sometimes even walk through them. There is also snow skiing for those interested in that, but I was there in the fall and colors were what I was interested in. If you ever get to Bayfield Wisconsin you must try the white bass they fish out of Lake Superior, really yummy!
The Apostle Islands are close by and you can take a ferry to Madeline Island, the largest island and/or boat or kayak around the islands yourself. There are beautiful beaches along the lake to walk along and a wonderful boardwalk trail as well. The weather was gorgeous while we were there so we were able to do lots of hiking. Oh and be aware of Green Bay Packer fans, they can be a little crazy!
Just a short distance southeast of Bayfield and along a beautiful scenic drive along the shores of Lake Superior you come to an area where several waterfalls occur close to Lake Superior, some of the highest in the state of Wisconsin. You can also white water raft down some of these rivers. We stopped at Copper Falls State Park and were able to do some hiking and enjoy the falls there.