Pleasant Hill Preserve on Pleasant Hill Road is a rare open space in one of Scarborough’s largest neighborhoods.  It includes headwaters of the Spurwink River, and abuts Rachel Carson National Wildlife Refuge.
Trails: 1.5 miles, including a Universal Access/ADA trail
Land: 135 acres
Open year round.
Leave no trace.

The Trails

Currently 1.5 miles of permanent trails.

Eleanor’s Trail is a Universal Access/ADA Trail, designed to accommodate wheelchairs, walkers and other assistive devices. It is a lovely 0.25 mile trail with views across the property.

Monty’s Trail is a 1.25 mile loop beginning and ending at the Swallow Barn, winding through fields and forest

How to get there

Get directions to the trailhead location.

Print a Trail Map

Download the Trail Map and print it to bring along when you visit.


  • Handicapped accessible trail.
  • Hiking, wildlife-watching, snowshoeing, cross-country skiing.
  • Dogs must be leashed at all times
  • No bicycles.
  • For the benefit of visitors and wildlife, no drones.
  • No hunting.

Want to join others who help maintain these trails for the community?


The Land

135 acres

Natural Features

Open fields, woods, wetlands, wildlife, and headwaters of the Spurwink River. More than 100 bird species recorded, including barn swallows that make use of the old metal barn. The Preserve is part of a wildlife and wetlands corridor that reaches from the Rachel Carson National Wildlife Refuge to the Scarborough Marsh.

History & Current Use

SLT purchased this land from the children of Jerrerd Benjamin in 2014. The land has a long farming history, and the metal barn is a remnant of days gone by. Mr. Benjamin owned the property for 40 years, and raised beef cattle and other animals. Previous owners included the Robinson family, who built a farmhouse and brick barn on the northwest side of the property, and the Johnson family, who had a house and farmed the southwest side of the property.

Support for the purchase and stewardship of this property came from individuals, foundations, and Scarborough’s Land Bond Fund.

Other Info

In 2018, we will be creating another permanent trail on the northwest side of the property, which will connect with Monty’s Trail.

Detailed natural history information can be found here (14MB pdf download).