Posted on May 11, 2022 and last updated on May 14, 2022

Whippoorwill Conservation Area, York


  • Preserve Size: Not sure
  • Trail Mileage: ~2.5 miles in trail system
  • Pets: yes
  • Difficulty: easy to moderate
  • Sights: Whippoorwill Pond, 1600s-era stone walls

This York Land Trust and Whippoorwill Landowners Association parcel forms the southwest corner of a fairly large subdivision between Route 1 and the highway. It includes forest paths, a trail that follows a charismatic stone wall, and a wetland area. On the day we visited, we saw many birds, including a couple of warblers, near the marshy pond.

When the land was a public “commons,” as long ago as the 17th century, it was divided with old stone walls. Some still stand today.

The trails are mostly flat and easy, but if you are seeking a very gentle trail—even a wheelchair accessible one—you can follow the dirt road from the Meadowlark Drive trailhead onto the York-Kittery water district land (which I plan to map one day!).

Meanwhile, there is another neighborhood path near the picnic table and small field, off Meadowlark Drive, that is pretty and moss-covered — just not very extensive.

There are two trailheads to the main trail system: one at the roundabout at the end of Meadowlark Drive and the other at the end of Kestrel Circle. There is really limited parking here but neighbors to the preserve say you can park a car or two on the shoulder of the center islands in both of these roundabouts. If you feel uncomfortable about doing that, you can also park in the shoulder of the road near the picnic area off of Meadowlark Drive. You’ll pass this area before reaching the trailheads. I’ve mapped all these areas on my Google map.


Let me know if you have any trail updates or corrections!