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Sheep Pond Woodlands Trail

4.8 ★★★★★ 16 Google reviews · Running trail in Brewster, Massachusetts · 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 Sheep Pond Woodlands Trail 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.

Sheep Pond Woodlands Trail — running trail in Brewster, MA, photo 1
Flat & fast

What runners say about Sheep Pond Woodlands Trail

Pulled from public reviews of this trail (16 of them) — the things people bring up again and again, in their own words. Nothing here is written by us.

I love this trail thought the woods 🌲 It's a shorter walk, maybe around 1.5 miles round trip. The beginning of the trail and many parts of it are covered by the canopy, so it's nice and cool in the Summer. My dog 🐶 loves to go for walks in this trail too.

★★★★★ — Peter , Dec 2022

Nice winter walk. Some tire tracks to follow to make it a little bit easier.

★★★★★ — Janis , Mar 2019

Great simple trail....somewhat rocky especially near pond. Great views.

★★★★★ — Mike , Nov 2023

Excerpts from public Google reviews. Read all 16 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.

➖ Flat & fast 2 mentions

“Bring your own bag 😁 Some of the terrain can be uneven with some rocks, so just be aware it's not all level ground if you're going for a hike.”

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Plan your run at Sheep Pond Woodlands Trail

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 Sheep Pond Woodlands Trail

Sheep Pond Woodlands, Brewster, MA 02631

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.

No Bottom Pond Trail

4.3 ★★★★☆ 7 reviews

Brewster, MA

Mixed

under a mile away

Eddy Bay Trail

4.7 ★★★★★ 46 reviews

Brewster, MA

LoopScenicDog-friendly

Popular forested trail that overlooks Cape Cod Bay.

1.4 miles away

Nickerson State Park

4.7 ★★★★★ 1,876 reviews

Brewster, MA

Scenic

Woodsy 1900-acre preserve featuring a large campground, trout-fishing ponds, biking & hiking trails.

2.3 miles away

Spruce Hill Conservation Area

4.5 ★★★★★ 13 reviews

Brewster, MA

2.3 miles away

Punkhorn Parklands

4.7 ★★★★★ 33 reviews

Brewster, MA

ScenicDog-friendly

2.4 miles away

Upper Mill Pond

4.5 ★★★★★ 12 reviews

Brewster, MA

Crushed gravel

2.4 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.