HomeWisconsinMilwaukee › Oak Leaf Trail - South Shore Line

Oak Leaf Trail - South Shore Line

4.9 ★★★★★ 14 Google reviews · Running trail in Milwaukee, Wisconsin · Hours vary

Runner's snapshot

Surface
Not reported
Distance
Not reported
Shape
Not reported
Shade
Not reported
Access
Not reported

We have not been able to confirm the surface, distance or shape of Oak Leaf Trail - South Shore Line yet from its own listing, the park's website or runner reviews — so those cells stay blank rather than guess. What is below comes straight from the listing and from reviewers' own words. 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.

What runners say about Oak Leaf Trail - South Shore Line

Pulled from public reviews of this trail (14 of them) — the things people bring up again and again, in their own words. Nothing here is written by us.

🏞️ beautiful scenery 3 mentions

“I always ride my mountain bike on the beautiful Oak Leaf Trail in nice weather heading south for many miles then riding back on it on the way home”

Very nice trail! We went a couple times in October and it was a beautiful time to visit. My husband and dog enjoyed the trail as well.

★★★★★ — Cassie , Jan 2025

I always ride my mountain bike on the beautiful Oak Leaf Trail in nice weather heading south for many miles then riding back on it on the way home

★★★★★ — Chris , Jun 2023

Excerpts from public Google reviews. Read all 14 reviews →

Plan your run at Oak Leaf Trail - South Shore Line

The practical stuff

  • AccessHours vary — hours are not posted for this trail, so check before an early or late 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.
  • Websitecounty.milwaukee.gov

Where to find Oak Leaf Trail - South Shore Line

2136 E Estes St, Milwaukee, WI 53207

Get directions

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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 Something out of date?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.