Running / biking / walking /rollerblading on the Lakefront Trail is one of our favorite past times. The Drake is conveniently located right by the Oak Street Underpass. Just north of the hotel, take the underpass to get you to the trail. It goes about 7 miles north from this spot, and about 20 miles south. There is a Divy station as well right by the Underpass entrance if you'd like to rent a bike.