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A Shelter Island view from the ‘Kissing Rock.’ (Credit: Charity Robey)

The view from SALT on Shelter Island.

20,000 years ago, as the glacier of the last Ice Age receded, a rocky island with a jagged shoreline was left between the North and South forks of what would someday be called Long Island. 

I’m sitting on one of those rocks on a sliver of sand beside Ram Island Dr., which connects Shelter Island and Little Ram Island. I’m gazing at the lighthouse that marks another pile of rocks, across the bay. Grateful for that glacial scouring that resulted in the many spots on Shelter Island with sweeping vistas, I’m about to celebrate this place the same way I celebrate everything. With food and drink.

Among the many joys of Shelter Island are the undeveloped, tucked-away spots that are ideal for a picnic, meditation or just “living slow.” These are places without a parking lot, bathrooms or even picnic tables. Here are three of my favorites, paired with food and drink inspired by the spot itself. 

Credit: Charity Robey
Credit: Charity Robey

Bootlegger’s Alley
At the end of Bootlegger’s Alley is a town landing, and to the south stretches a long, lovely beach that extends to Crab Creek Point.

Since the time of Prohibition, the consumption of alcohol has figured in the history of this beach, so it seems appropriate to spread out the blanket, pull out a deliciously-retro bacon, lettuce and tomato sandwich (whole wheat toast of course) from the Eagle Deli (25 West Neck Rd.),  and open a bottle of Riesling from the now closed Peconic Bay Winery

Credit: Charity Robey
Credit: Charity Robey

Burns Road Picnic Spot

Near the east end of Burns Road, a single picnic table perches on a grassy rise, with views of the salt marsh and Coecle’s Harbor.

This is a spot to enjoy something spicy from Maria’s Kitchen (55 North Ferry Rd. at Jaspa Rd.), and a small growler of Spring Turning Rye Saison from Greenport Harbor Brewery (234 Carpenter St., Greenport.)

Maria’s Chicken Burrito is a reliable favorite, but I’m most partial to Maria’s Salad with Shrimp. It is ample for two, stuffed with large shrimp, avocado, corn, cilantro and her terrific balsamic vinegar dressing. 

Credit: Charity Robey
Credit: Charity Robey

Kissing Rock Landing

At the west end of Rocky Point Ave. is a big rock, on a small pebbly beach with a great view across Southold Bay.

Nature has even provided some “picnic tables” — several large boulders that are almost flat enough to prevent a sandwich from rolling off.

A romantic, sunset-watching location, this is the perfect place to share some Shelter Island “small plates.” On my menu is a cheese platter with a fresh-baked baguette from Reddings (184 North Ferry Rd.) with a cupcake-sized serving of Grandmama’s Chocolate Cake.

To drink, I’ve brought a bottle of Wickham’s Pear Cider from Shinn Estate Vineyards, (2000 Oregon Rd., Mattituck.) This golden-colored, lightly sweet and slightly-bubbly hard cider is made from pears grown on a Cutchogue farm that’s been in the same family for three centuries — a long time, but not nearly as long as this rock has been here.

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