A small outpost for the harvesting of sassafras was occupied for a few weeks in 1602, arguably making it the first English settlement in New England.

It is home to a wide variety of birds such as piping plovers, least terns and Massachusetts' American oystercatchers,[3] as well as White-tailed deer, White-footed mice, and Eastern cottontails.

The Lookout is home to one of the six (one now buried) defensive bunkers built by the United States Coast Guard in 1941 to watch the surrounding ocean for Nazi U-boats.

Stripped of their observation equipment and weaponry at the end of World War II, the bunkers are now picnic areas.

Many of these guides troll secret lures attached by stainless-steel or nickel-alloy wire along the rocky reefs near the island where large female striped bass reside from the spring through the autumn.

On March 6, 1602, Gosnold set out aboard the barque The Concord from Falmouth, England to plant a colony in the New World of America.

Gosnold and his men landed near Kennebunkport, Maine, then explored Cape Cod, Martha's Vineyard, and Cuttyhunk.

They established a modest fort on Cuttyhunk where they planned to harvest sassafras, a valuable commodity in Europe at the time.

Stirling sold the islands to Thomas Mayhew in 1641, and in 1663 James Stuart, Duke of York assumed proprietorship over them.

In 1668, Mayhew sold Cuttyhunk to Philip Smith, Peleg Sanford, and Thomas Ward of Newport, Rhode Island.

In 1688, Peleg Sanford acquired his partners' rights in the island, and sold half of it to Ralph Earle of Dartmouth.

He in turn immediately sold his property to his son, Ralph Jr., who became the island's first permanent English settler.

Swift, Thomas Nye, and Eben Perry bought Cuttyhunk from Otis Slocum for fifty dollars.

Every Fourth of July, the club would host a party for island residents, including fireworks displays.

He invited other young, wealthy couples who were his friends to purchase summer homes on the island, to provide playmates for his children.

Men stood atop Lookout Hill with spyglasses in hand, scanning the horizon for incoming whaling ships headed for New Bedford.

There is one bed and breakfast - the Cuttyhunk Fishing Club - and many home rentals for summer tourists, but given its small size, other facilities on the island are limited, with three retail stores and only a few spots for lunch or dinner.

[11] The single school on the island had one teacher and three students as of August 2009; in June 2019, eighth grader Gwen Lynch graduated as the sole member of the Class of 2019.

The school has plans to reopen as a STEAM Academy, which would offer weeklong seminar-style programs in lieu of having full-time students on-island.