Shelter Island
Every cool kid in the know will tell you that going out east shouldn't stop after Labor Day. Shelter Island is the perfect place for a waterfront weekend away, even in the fall. Rent a bike and wake up with a brisk ride around filled with foliage and make sure you stay at the chic B&B, The Chequit.
The Chequit, 23 Grand Ave, Shelter Island Heights, NY
[Photo via @motleycollections]