wellness
Midtown's Top Walking Trails Rated by Distance and Difficulty
Runners and walkers can pick routes across Oakwood Park and the riverfront based on exact lengths and terrain ratings from city maps.
How we reported this
Midtown Parks and Recreation released updated trail ratings on July 1 that sort five local paths by measured distance and difficulty levels from easy to strenuous.
July daylight stretches past 9 p.m. this month, giving residents extra hours after work to reach the trails before sunset. The Midtown Active Living Program reported a 22 percent rise in trail check-ins during the first week of July compared with the same period last year, a shift tied to the city's summer wellness push that promotes outdoor movement over indoor gym sessions.
Oakwood Park and Riverside routes lead the list
The Oakwood Park Loop starts at the entrance on 14th Street and covers 1.8 miles of flat gravel with one gentle slope, placing it in the easy category for beginners or recovery days. A few blocks east, the Riverside Path runs 4.3 miles along the Midtown River from the 22nd Street boat launch to the old rail bridge, rated moderate because of two short inclines and uneven sections near the water's edge. Both sites fall under maintenance by the Midtown Parks and Recreation crews, which clear debris weekly through September.
Further out, the Hilltop Connector begins at the Oakwood Park north gate and extends 7.9 miles into the wooded ridge behind the former textile mill on Maple Avenue, earning a difficult rating for its 650-foot elevation gain and rocky patches that require sturdy shoes. The Midtown Wellness Council added signage at all three trailheads last month listing exact distances and difficulty scores so users can plan routes without guesswork.
Usage data and access details
City records show 14,800 trail visits logged through the Midtown Parks app between June 1 and July 8, with the Riverside Path accounting for 41 percent of those entries. Entry remains free at every location, though the Midtown Active Living Program charges $12 for an optional printed map booklet sold at the Parks office on 9th Avenue. Parking at the 14th Street lot fills by 8 a.m. on weekdays, while the Riverside boat launch offers 45 metered spaces at $1.50 per hour.
Residents can download the updated ratings from the city website or pick up paper copies at the Midtown Library branch on Elm Street before heading out. Checking the Parks Department social feed each morning provides same-day notes on any temporary closures due to recent rain or maintenance.