Summer-Ending Ritual: Shelter Island Bike Ride

Sure it was tough to say a calendar-mandated so long to summer this week, but aren’t we lucky that the memories linger? One of my favorite rituals is a season-ending Shelter Island bike ride that blends a cardio-boosting workout with catch-up conversation.

My friend Lisa organizes this social ride each year, bringing together friends from different parts of her world – tennis, cycling, teaching. This year, a dozen joined in, including several teen daughters. Chat along the mostly shaded roads centered on our kids, work, books and anticipated plans for autumn.

The morning kicks off from South Ferry in North Haven, just north of Sag Harbor, for the breezy 5-minute cruise across Long Island Sound. Shelter Island is a good pick for a half-day excursion since the route works for all levels of riders. Short climbs on Ram Island can be walked or skipped, and the roads are quieter than in other parts of the Hamptons.

The island offers up boundless water views from marinas crowded with pleasure craft to calm inlets lined with osprey nesting platforms. Our route extended east to Ram Island, then north along Shore Road in Dering Harbor, where wooden power boats bob along the docks in front of stately waterfront homes. We paused for coffee at our perennial favorite, Star’s Café, in Shelter Island Heights, before taking in the views at Rocky Point Road.

The reward for pedaling was lunch of steamers, fries and chilled glasses of wine, beneath the awning of the upper-deck restaurant at Andre Balazs’s Sunset Beach Hotel. Then it was time to loop back to the ferry.

Here’s to annual bike-riding rituals that keep summer memories coming. Thanks Lisa (third from right), for bringing us together!

More for you:

Shelter Island Route Map

My Shelter Island post for Well + Good Shelter

Photos: velojoy and 2 bottom, Susan Ehrlich

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