For a wooded and moderately challenging trail run right near downtown, head to Chester Park. The Chester Park Trail is wooded and steep with some occasionally challenging footing, going up and down ravines. There are footbridges and lovely waterfalls. The main loop, along each side of Chester Creek, is ~2.5 miles, though another 0.5 miles can be added on the west (Chester Bowl) side, which is more open. From the trailhead at S. 14th & 4th, it’s a steady and steep climb to the Upper Park, which is less technical, but hilly. Note: the trails are used for winter sports, please use etiquette.
Add-Ons/Longer Run: The University of Minnesota at Duluth, just east of Chester Park, has some nice paths and interesting buildings. There’s also a great track for running at Malosky Stadium. You can also connect to the Hartley Nature Center trails from the University, using the a trail through the Bagley Nature Area. It can be accessed just behind the library.