Labor Day is bearing down on us and it is going to happen, and with it summer will be coming to an end. But Shelter Island plans on making it a weekend so chockfull of all things summer.
Wake up early on Saturday and head out with your fishing gear in search of the best catch for the annual Shelter Island Snapper Derby. Postponed by weather woes thanks to Hurricane Danny, the Derby is a great way to show off fishing skills.
The Chequit Inn will host The Realm Saturday night- one of the most popular local Hamptons bands from 10pm-1am. With the fastest bartenders on the island and a guaranteed dance party, it is the place to spend your Saturday night on Shelter Island.
Nothing quite beats a Sunday on Shelter Island. First, head to The Pharmacy for the best egg sandwich this side of anywhere. More important than how delicious it is, it is the best cure for a hangover. After a great breakfast head over to Crescent Beach and watch the boats drift by. If lazing on the beach isn’t your thing, there is always golfing at The Shelter Island Country Club, or as locals call it, Goat Hill. It is the highest point on Shelter Island so if your handicap isn’t what you wish it was, at least you can enjoy 360 views of the island.
Finish your Sunday off at The Ram’s Head Inn for Jazz Night, featuring Rebecca Dorsey. Dine outdoors or head into the bar for cocktails and appetizers, just be sure to get there in time to catch the sunset over Coecles Harbor, visible from nearly every seat in the house.
As you head back on Monday, enjoy the salt air as you are ferried back to the mainland. And remember that fall on Shelter Island is also a season not to be missed.
By Kelly Gillooley














