On the East End, there’s the North Fork and there’s the South Fork, and then there’s a little something in between. Shelter Island was cool before becoming a hashtag on Instagram, you just didn’t know it unless you, well, knew it. Settled in the mid-1650s, around the same time as the towns lining the twin forks, this small town spans less than 30 square miles, and proudly belongs to neither the North Fork or the Hamptons. Shelter Island is its own entity, but at least has two ferries to get you on and off the island, should you ever so choose.

There are only 15 weekends from Memorial Day to Labor Day, with 93 official days of summer. We’re now in the thick of it, soaking up every afternoon at the beach or night out dining alfresco. The cool tranquility and casual vibes of the North Fork are an attraction for those who live near and far. If you live near, you can probably expect guests for long weekends at some point or another. And while we essentially live outdoors in the summer months, being backyard-ready is a must every fair-weather season.