Bayfield Loop148 Miles (3 hours)
This is the granddaddy of the drives on this list in terms of distance, but the payoff is well worth it! Start your journey with a blend of farms and forest along Highway 13, eventually giving way to forests and Lake Superior shoreline.
The pinnacle of this loop is at the other end, along Chequamegon Bay. Seeing sailboats against a multi-colored shoreline and vibrantly colored islands dotting the bay makes almost any picture you take postcard-worthy.
Bayfield is famous for their annual apple festival, which sees thousands of people coming to town for one weekend every fall. While the festival is a lot of fun, you can also enjoy the same incredible scenery and apple-filled fun during most of the fall season. Walk down the streets, check out the shops, or enjoy some waterside dining at one of the many places to grab a bite to eat, like the Pier Plaza Restaurant.
A number of other small towns along the shoreline offer other opportunities to stop and walk around, with nearby Ashland offering a number of additional dining and adventure options. My personal favorite place to grab a meal and a beverage in Ashland is the Deep Water Grille, which features Ashland-brewed South Shore Brewery Beer.
While many of these loops and routes can be started and finished in no particular order, I recommend taking Highway 13 East, and Highway 2 back. While scenic, Highway 2 isn't nearly as scenic as the first part of the route, and it will allow you to get home quicker after a long day.