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Pleasant Bay Woodlands

4.8 ★★★★★ 6 Google reviews · Running trail in Harwich, 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 Pleasant Bay Woodlands 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.

Stroller / ADATrailhead parking

What runners say about Pleasant Bay Woodlands

Pulled from public reviews of this trail (6 of them) — the things people bring up again and again, in their own words. Nothing here is written by us.

Wonderful short hike, easily accessible from Wequassett Inn. Larger trail leads down to cranberry bog with a smaller wooded trail returning to parking lot. Parking lot has space for 6 to 8 cars. Hike down larger trail is easy and very accessible. Hike through woods is easy, but trail is very narrow.

★★★★★ — Parker , Jun 2021

Excerpts from public Google reviews. Read all 6 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.

🅿️ Trailhead parking 2 mentions

“Larger trail leads down to cranberry bog with a smaller wooded trail returning to parking lot.”

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Stroller / ADA accessible 2 mentions

“Wonderful short hike, easily accessible from Wequassett Inn.”

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Plan your run at Pleasant Bay Woodlands

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.
  • At the trailheadparking — reported by runners
  • Stroller / wheelchairReported as smooth and step-free enough for a running stroller or a chair.
  • Websiteharwichconservationtrust.org
  • Phone(508) 432-3997
  • Social Instagram

Where to find Pleasant Bay Woodlands

75 Kendrick Rd, Harwich, MA 02645

Get directions

Running trails near Harwich

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

Jackknife Cove

4.6 ★★★★★ 61 reviews

Harwich, MA

Scenic

Relaxed beach on Route 28 overlooking Pleasant Bay.

under a mile away

Hawksnest State Park

4.6 ★★★★★ 119 reviews

Harwich, MA

ScenicDog-friendly

Quiet locale for hiking, relaxation & wildlife viewing in a natural setting with woodlands & ponds.

2.0 miles away

Old Colony Rail Trail Trailhead

5 ★★★★★ 2 reviews

Chatham, MA

2.8 miles away

Thompson's Field

4.8 ★★★★★ 16 reviews

Harwich, MA

Dog-friendly

3.0 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.

3.0 miles away

Thompson's Field Conservation Area

4.7 ★★★★★ 109 reviews

Harwich, MA

ScenicDog-friendly

Nature preserve featuring native plants, trees, and shrubs, and hiking trails that welcome dogs.

3.5 miles away

All running trails in Harwich, 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.