5. Cuttyhunk Island, Massachusetts
History buffs may argue that this secret island is the first English settlement in New England (at some point in 1602, it served as a small outpost for harvesting sassafras), while literary buffs may hold the controversial opinion that it inspired Shakespeare’s “The Tempest”.
No matter which side you’re on, this destination off the Massachusetts coast is short on people but full of history. The piece of land is only 1.5 miles long, with half of it being a nature reserve. There are only 10 people that live here year-round, but during the summer months, tourism flourishes, and most visitors get around by golf cart or bike.
Picnickers can enjoy lovely spots packed with history, such as a World War II lookout, and you can try the delicious striped bass (fun fact: the island is known for big striped bass; two world-record catches of 73 pounds each have been documented here).
