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Loop Trail

Running trail in Winchester, Massachusetts · Hours vary

Runner's snapshot

Surface
Not reported
Loop distance
Not reported
Shape
Loop
Shade
Not reported
Access
Not reported

Confirmed from Loop Trail'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.

Loop Trail — running trail in Winchester, MA, photo 1
Loop

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.

🔁 Loop trail

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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.

Where to find Loop Trail

Chardon Rd, Winchester, MA 01890

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Running trails near Winchester

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

Brooks Parkhurst Town Forest

3.3 ★★★☆☆ 3 reviews

Winchester, MA

under a mile away

Medford-Brooks Estate Land Trust

4.6 ★★★★★ 37 reviews

Medford, MA

Boardwalk

under a mile away

Mystic Lakes State Park

4.6 ★★★★★ 926 reviews

Medford, MA

ShadedScenic

State park featuring a sandy beach, hiking trails, and areas for boating.

under a mile away

Cross Fells Trailhead

4.1 ★★★★☆ 8 reviews

Medford, MA

under a mile away

Wright's Pond Park

4.8 ★★★★★ 141 reviews

Medford, MA

Scenic

Clean park featuring a sandy beach, a pond, picnic tables, playgrounds and walking trails.

1.8 miles away

Horn Pond Mountain

4.7 ★★★★★ 7 reviews

Woburn, MA

1.8 miles away

All running trails in Winchester, MA →

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.