The Hamptons · Shelter Island

Shelter Island

The ferry-only island between the forks, Mashomack Preserve, and an unhurried rhythm that most Hamptons weekenders never access.

Shelter Island is the ferry-only middle ground between the North and South Forks. The Mashomack Preserve covers a third of the island. Crescent Beach, the Ram's Head Inn, and the Sunset Beach hotel each shape a different version of the weekend. The ferry schedule keeps the crowd self-selected, and the island's year-round energy runs closer to the quieter Shelter Island version than the South Fork summer circus. For adults 21+, the cannabis-aware rhythm here pairs with private-rental consumption, long afternoons on the beach, and an early sunset dinner. The nearest licensed dispensaries are a ferry-plus-drive away on either fork.