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Upper Mill Pond

4.5 ★★★★★ 12 Google reviews · Running trail in Brewster, Massachusetts · Posted hours

Runner's snapshot

Surface
Crushed gravel
Distance
Not reported
Shape
Not reported
Shade
Not reported
Access
Posted hours

Confirmed from Upper Mill Pond'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.

Upper Mill Pond — running trail in Brewster, MA, photo 1
Upper Mill Pond — running trail in Brewster, MA, photo 2
Upper Mill Pond — running trail in Brewster, MA, photo 3
Upper Mill Pond — running trail in Brewster, MA, photo 4
Upper Mill Pond — running trail in Brewster, MA, photo 5
Crushed gravel

What runners say about Upper Mill Pond

Pulled from public reviews of this trail (12 of them) — the things people bring up again and again, in their own words. Nothing here is written by us.

Entering from the north going soth, it is a paved road. Other entrance is gravel. Free parking in a gravel lot near the launch at Upper Mill. Hiking trails are maintained, but markings can be confusing. Seymour Pond entrance is a shallow rocky tree tunnel entering into the pond.

★★★★☆ — Laura , Aug 2021

Excerpts from public Google reviews. Read all 12 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.

🪨 Crushed gravel / limestone 2 mentions

“Other entrance is gravel.”

More trails like this →

Plan your run at Upper Mill Pond

The practical stuff

  • AccessPosted hours — posted hours below; park gates sometimes close earlier than the listing says
  • SurfaceCrushed gravel — the rail-trail classic: softer than asphalt, still smooth enough for tempo work
  • 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.

Hours

Monday 7 am–10 pm
Tuesday 7 am–10 pm
Wednesday 7 am–10 pm
Thursday 7 am–10 pm
Friday 7 am–10 pm
Saturday 7 am–10 pm
Sunday 7 am–10 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 Upper Mill Pond

Brewster, Massachusetts

Get directions

Running trails near Brewster

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

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Drummer Boy Park

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Wing Island

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Crowes Pasture Conservation Area

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Sandy beach and mudflat destination that offers off-road vehicle access for a permit fee.

2.0 miles away

Eddy Bay Trail

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LoopScenicDog-friendly

Popular forested trail that overlooks Cape Cod Bay.

2.2 miles away

All running trails in Brewster, 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.