Quick Weekend in Shelter Island

Traveling during the Covid-19 pandemic has been a little challenging, so when we got the opportunity to stay at a house on Shelter Island for a 3 day weekend, we quite literally jumped at the chance.

GETTING THERE:

We drove through the North Fork (stopping at a few Farmers Market’s along the way), and then took a 5 minute ferry ride from Freeport (there’s also a ferry in Sag Harbor if you’re coming from the South). Make sure to bring cash as it’s cash-only!

STAY:

Majority of the popular hotels are closed due to Covid (The Chequit Sunset Beach, and The Pridwin), so your best bet will be an airbnb or calling a broker to rent a property this Summer!

EAT:

Vine Street Cafe — They weren’t doing in-dining seating while we were in town, but I’ve heard this is an incredible restaurant and worth a reservation! Sunset Beach — Known for being the most “hamptons” thing about Shelter Island. This sceney spot is always hopping during the Summer months. Marie Eiffel Market — Great spot for picnic supplies, breakfast, lunch, fresh food, snacks, etc. Shipwreck at Salt — Super cute bar, Isola — Great local Italian spot , and Commander Cody’s — Awesome seafood!

DO:

Enjoy the beaches: Shell Beach, Crescent Beach, Wade Beach, Silver Beach, or Hay Beach

Bike around the Island. We had so much fun exploring different areas of Shelter Island (and beaches!) by bike. The roads are pretty empty so you will feel totally safe doing so.

Grab your sneakers and hike/walk the Mashomak Preserve trails. You could easily spend a few hours here, and there scenery changes from marsh, to ocean, to forests and prairie. Very beautiful!

Check out the Sylvester Manor Farm Stand for the freshest fruits and vegetables. I ate the best snap peas of my life from here!