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Winston Woods Park, Bolingbrook Park District

4.4 ★★★★☆ 68 Google reviews · Running trail in Bolingbrook, Illinois · Posted hours

Runner's snapshot

Surface
Mixed
Distance
Not reported
Shape
Not reported
Shade
Not reported
Access
Posted hours

Confirmed from Winston Woods Park, Bolingbrook Park District's own listing, the park or land manager's website, and runner reviews. Blank cells mean we could not verify that fact — we would rather say "not reported" than invent one. There is no Easy / Moderate / Hard rating on this page on purpose: a one-word difficulty score tells you nothing about whether a trail suits your run. Surface, distance, shade and hours do.

MixedScenicStroller / ADARestroomsTrailhead parking

Park with a playground, paved and natural trails, and a picnic shelter.

What runners say about Winston Woods Park, Bolingbrook Park District

Pulled from public reviews of this trail (68 of them) — the things people bring up again and again, in their own words. Nothing here is written by us.

well-maintained 4 mentions

“Beautiful Park nice and clean Porta-Potty was clean all all together I like it”

🏞️ beautiful scenery 6 mentions

“Absolutely beautiful day with grandkids and my family a lot of activity with deer lot of bike riders very nice”

Beautiful forest area for walking and enjoy a natural scene. Be careful I have seen one coyote in the past few years.

★★★★★ — Rebel , May 2019

Nice trails and clean. Play area could be a bit bigger, but was newly remodeled.

★★★★☆ — Eric , Apr 2022

Nice pavilion area. Went for a walk through wooded path. Kid area nice

★★★★☆ — Kim , Jul 2021

Excerpts from public Google reviews. Read all 68 reviews →

Trail conditions & character

What this trail is actually like underfoot and overhead, taken from its own listing and from reviews. Each one links to every other trail with the same character. Busy or quiet is reported as a plain fact, not a plus or a minus — a runner heading out alone at dawn often wants company on the path, and someone running intervals wants an empty one.

🏞️ Scenic views 6 mentions

“Absolutely beautiful day with grandkids and my family a lot of activity with deer lot of bike riders very nice”

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🛣️ Paved surface 2 mentions

“great location- love the park and paved or natural trails.”

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🚻 Restrooms

“Beautiful Park nice and clean Porta-Potty was clean all all together I like it”

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🅿️ Trailhead parking

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🌲 Natural surface / singletrack

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Stroller / ADA accessible

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Plan your run at Winston Woods Park, Bolingbrook Park District

The practical stuff

  • AccessPosted hours — posted hours below; park gates sometimes close earlier than the listing says
  • SurfaceMixed — more than one surface along the route, so check the segment you plan to run
  • DistanceNot reported. Trail systems often quote total path mileage rather than a single loop, so measure the route you actually want before you drive out.
  • ShadeNot reported. Assume some of it is exposed and carry water in summer.
  • At the trailheadparking, restrooms — reported by runners
  • Stroller / wheelchairReported as smooth and step-free enough for a running stroller or a chair.
  • Websitebolingbrookparks.org
  • Phone(630) 739-0272

Hours

Monday 7 AM–9 PM
Tuesday 7 AM–9 PM
Wednesday 7 AM–9 PM
Thursday 7 AM–9 PM
Friday 7 AM–9 PM
Saturday 7 AM–9 PM
Sunday 7 AM–9 PM

Posted hours for the park or trailhead. Gates and parking lots often close earlier than the trail itself, and seasonal hours change — worth a check before a pre-dawn or after-dark run.

Where to find Winston Woods Park, Bolingbrook Park District

320 Charlestown Dr, Bolingbrook, IL 60440

Get directions

Running trails near Bolingbrook

Other trails within easy driving distance — useful when this one is flooded, gated, or just not the run you had in mind today.

DuPage River Greenway Trail

4.6 ★★★★★ 67 reviews

Bolingbrook, IL

Paved

Park offering kid-friendly hiking, trout, and opportunities to see birds.

under a mile away

Mending Wall Park

4.8 ★★★★★ 96 reviews

Woodridge, IL

Open space boasting a playground, swings, slides, a rope tower and a jogging path.

under a mile away

Gateway Wetlands Park, Bolingbrook Park District

4.3 ★★★★☆ 36 reviews

Bolingbrook, IL

MixedShaded

1.0 miles away

Greene Valley

4.7 ★★★★★ 986 reviews

Bolingbrook, IL

MixedShadedScenicDog-friendly

Massive park with trails for hiking & cross-country skiing, plus picnic areas & camping facilities.

1.3 miles away

Echo Point Park

4.4 ★★★★☆ 98 reviews

Woodridge, IL

Shaded

Relaxed park featuring a playground with swings, slides and climbing areas, plus picnic tables.

1.4 miles away

James S. Boan Woods, Bolingbrook Park District

4.7 ★★★★★ 26 reviews

Bolingbrook, IL

Natural surface

1.6 miles away

All running trails in Bolingbrook, IL →

Nearby towns

Listing verified July 2026 from public records, the trail's own website and runner reviews. Trail conditions change — paths flood, gates close at dusk, and shaded woods stay muddy for days after rain. Something out of date? Report a correction. Manage this trail? Send us the details — it is free.