Day Trip With Diane Strecker

It is the perfect summer day to forge east. The sky is a massive blue and a soft warm breeze skips over a glistening bay. A light mist from the ferry wake sprays up to welcome you as you arrive at a place that sings all that is summer. A string of old captain’s homes along the shoreline and an array of brilliant sails come into view. It is easy to let your mind shift back a gear as the tiny transport docks at one of the best-kept secrets on the East End, Shelter Island.

The small isle, so aptly named, is protected on both sides by the two forks, making it easily accessible from the Hamptons via North Haven or from Greenport by way of the North Fork. Each crossing takes but a few minutes yet carries you to a place where everything is quaint, from the gas station to the local inn. [expand]

First stop off the North Ferry is the historic Shelter Island Heights. Highly sought-after gingerbread-style Victorians and antique cottages that date back as far as the 1600s line the streets to town. But don’t blink or you will find yourself already in the harbor from and miss lunch on the patio of the Chequit Inn that overlooks the harbor high on White Hill. The neighboring shops include an old-fashioned drugstore that still has a soda fountain, a very well-equipped hardware store and the local sandwich shop.

The area merchants are always worth a look. One of my favorites is the Coastal Cottage where you can surely find something “beachy” for your summer rental, or as a memento to tote back home.

The island is full of surprises and one that will completely floor you is the Sunset Beach resort. As you pass round the bend out of the Heights on the north side (follow the signs), a vista opens you will not believe. No need to pinch yourself or ask if you’ve entered the south of France; I can assure you—you are still on Shelter Island.

However, the real skinny this summer on the island is the opening of La Maison Blanche, a new restaurant and boutique-style hotel that even has the locals talking. The recently renovated 1800s inn is causing quite the stir.

Most everything on Shelter Island can be accessed off Route 114, the main route through the island. Following that road north to south you can always grab a bite at Kyles, a cool and comfortable respite that offers great food and cooking lessons!

And, if nature is what you’re after you’ve come to the right place. Bring bikes on your car or ride them onto the ferry. Shelter Island provides a bounty of exploration. On the south side is Mashomack Preserve, which makes up at least one third of the island’s 8,000 acres and is forever protected by the Nature Conservancy. Stop at the visitor center and get a map because a full hike is 11 miles. Make sure that you protect yourself from deer ticks with the proper clothing. Birdwatching is also a favored pastime here.

Another site on the island rich with history and natural beauty is the 243-acre Sylvester Manor. The property has served as a working farm since 1652 and has been in the same family for 15 generations. The 1810 wind-powered gristmill, made from local trees, still stands. The estate now operates as an educational facility and is open to visitors.

There is also an island within the island on the eastern-most side, appropriately named “Little Ram Island.” You can easily find it by following the signs along the main route, 114. Here you will find another historic inn, The Ram’s Head, overlooking Coecles Harbor. Dine out on the slate patio or get a drink at the vintage bar and sip it out on the lawn.

Shelter Island brands its own unique blend of country feel, history and sophistication. It is so beautiful and rich with attributes that both forks would like to claim. But as you will see when you visit, this is one island that clearly stands on its own.

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