Madison is the city between two lakes, so why not explore both shores with this loop around the spit of land that runs between them? This neighborhood run utilizes the Yahara Parkway, The Capital City Trail, and several other side streets for an interesting run through central Madison. Combination of trail and several pleasant residential streets with with good sidewalks.
Start in James Madison Park in the Old Market District. Take Gorham Street north and continue left onto Sherman Ave. In Tenney Park, the Yahara River Bike Path will bring you along the canal that connects Lake Mendota to Lake Monona. After heading southwest on the Capital City Trail along Lake Monona for 2 miles, Broom Street and Gilman will connect you back to James Madison. Tenney Park is also a great spot in winter for ice skating.