Running trails in Highwood, IL
Highwood has 1 trail in the directory — 1 open 24 hours. Every one posts opening hours, so you can check the gate before an early start. They're ranked here by rating weighted by review volume, across 191 Google reviews. Filter by surface, loop, distance, shade or lighting to get to the run you're actually planning — no made-up difficulty score, just the facts you'd check before driving out.
Openlands Lakeshore Preserve at Fort Sheridan: Main Entrance
4.6 ★★★★★ 191 reviews
MixedScenic
Lakeside nature preserve with kid-friendly hiking, trails, and murals.
No trails match those filters.
How to pick a trail in Highwood
- Match the surface to your legs. Most of what's here is mixed (1 of 1). Asphalt and concrete are fast, predictable and runnable year-round but the least forgiving; crushed limestone and dirt take the sting out of high mileage; boardwalk is flat and scenic but slick in the wet. If your shins or knees are complaining, the fix that actually works is varying the surface you run on rather than chasing one "best" one. More mixed trails →
- Loop or out-and-back? A loop finishes back at the car with no backtracking; on an out-and-back you simply turn round at half your distance.
- Check the hours before a 6am run. Every trail in Highwood is listed as open 24 hours, so an early start is never the problem. 1 of the 1 listing carries posted opening hours — worth a look before you set an alarm.
- Long run? Check water and restrooms first. 1 has trailhead parking in Highwood. Anything over an hour and those stop being nice-to-haves — and in summer, shade counts double.
- The small things that decide it. 1 that runners describe as quiet and 1 smooth and wide enough for a stroller or a wheelchair. Busy or quiet isn't a good-or-bad thing here: a busy path is the safer choice for a solo run at dawn, a quiet one is better for intervals.
More on all of this in the trail-running guides.
Browse Highwood trails by type
Running trails near Highwood
Worth the short drive — the closest towns with trails in the directory.