Jacknife Beach || Olivia’s Trench

Jacknife Beach sits along Pleasant Bay, offering a unique mix of a sandy beach and shallow tidal flats, making it perfect for families with small children. It’s also a popular spot for kayaking, paddleboarding, and fishing, with beautiful views of the bay. The waters are calm, and the beach is generally quieter than some of Chatham’s more popular spots. When the land was first settled, a large trench was dug there where a battle ensued. The trench was named for an estate landowner's daughter who was an intimate of one of the soldiers. While the soldier died heroically in battle, her fate is unknown. Parking is limited, but manageable, and a permit is required during the summer. Fires are not allowed on this beach.