High Five

About the Property

This is a great spot to see a great view that's just a short walk away from your car. The Forest Society hosted a timber sale on the property in 2007 when the views from the top were enhanced. This property is a fantastic place to enjoy an afternoon picnic or a quiet sunset. 

Trail Information

Wilson Hill Trail

Round-trip Distance: 
0.70 miles

A short (1/3 mile) hike along a moderately sloped woods road brings you to the top of Wilson Hill, from which you have a fantastic panoramic view to the north and west. There are no other trails on the property, so exploring further requires bushwhacking.

Property Details

The Forest Society purchased High Five with donated funds in 2004. It got its name when several members of the Forest Society's Land Management staff walked to the top and looked out at the expansive view. One of the staff members remarked that he just wanted to give a “high five," and the name stuck.

Recommended Properties Nearby


54 acres


Access to the property is from the south via Sky Farm Road in Deering. From the town of Hillsborough, take Route 149 East for 1.6 miles and then take a slight right onto Old County Road. Follow this road for 4.2 miles and then turn right onto Sky Farm Road. The property is located on the right after 0.8 miles. Parking is only available along the shoulder of the road.

You will see a green gate and property sign. Please remember not to block the gate. *Winter Access: This property does not have plowed parking.*

Recreational Opportunities

  • Birdwatching
  • Family-oriented
  • Great Views
  • Hiking Trails
  • Hunting
  • Snowshoeing


  • Pull-off parking


  • No Motorized wheeled vehicles (ATVs, trucks, dirt bikes)
  • No Camping
  • No Fires
  • Carry in, Carry out all trash
  • Do not disturb plants, animals, or cultural features