Another local favorite for off-street running, Head of the Plains is a Nantucket Conservation Foundation property located near Madaket in the southwest of the island. This nearly 1,000 acre area consists of grassland, shrubland, and pine forest, with trails that are a combination of old dirt roads and grassy loops.
The best place to start is the lot off the intersection of Madaket Road and Barrett Farm Road. There, you can follow the dirt road along West Hummock Pond for 2.5 miles one-way out to an ocean view. There are also some shorter grassy loops that are marked with Landbank signs. Chances are good you’ll have the place to yourself — very few people visit this property even in the summertime! Not to say it isn’t spectacular…Head of the Plains is a highly unique sandplain grassland habitat, cherished by environmentalist as one of the world’s best examples of this rare ecosystem.