East Head Pond – Bentley Loop Trail loop from East Head Pond

United States

Massachusetts

Plymouth County

East Head Pond – Bentley Loop Trail loop from East Head Pond

Easy

4.5

(6850)

11,294

riders

East Head Pond – Bentley Loop Trail loop from East Head Pond

01:49

24.7km

150m

Gravel riding

Easy gravel ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: September 9, 2026

Waypoints

Start point

Parking

Get Directions

4 m

Myles Standish State Forest Headquarters

Highlight • Forest

Myles Standish is a state forest and the biggest public recreation area in Massachusetts. The park has 16 lakes and kettle ponds surrounded by pine and oak forests. You can …

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124 m

East Head Pond

Highlight • Lake

East Head Pond, or Reservoir, is a picturesque 92-acre pond located on the south end of the Myles Standish State Forest. The pond is situated in a unique forest community …

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3.50 km

Bentley Loop Trail

Highlight • Trail

A wonderful trail through Myles Standish State Forest. For the past 30 years, it's been maintained by Bob Bentley, a founding member of Friends of Myles Standish State Forest. The …

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8.39 km

Halfway Pond

Highlight • Lake

The views of the pond are spectacular from this road.

Halfway Pond, a 232-acre warm water pond nestled in Plymouth, Massachusetts, sits between Myles Standish State Forest and Long Pond. …

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21.6 km

Fearing Pond is stocked with trout for fishing, and there is a public beach on the southeast shore. Camping is available around its perimeter, offering a night under the stars in beautiful, peaceful surroundings.

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