A Sweet Shelter Island Bike Ride (With Map)

Shelter Island Susi Wunsch

Susi Wunsch is a New York City cycling advocate and founder of Velojoy, a stylish online resource devoted to the cycling scene, sport, and lifestyle, which just came out with a comprehensive Hamptons biking guide.

For Well+Good, Wunsch created this scenic 20-mile ride that makes for a gorgeous Saturday morning on the historic summer sailing haven of Shelter Island. It comes with a handy map for your smart phone.

Get your bike, basket, and bell, and follow this summer cycling route, with a planned stop for lunch at Andre Balazs's Sunset Beach.

Note to riders: While the roads off Route 114 are quiet, they don't generally have shoulders, so riding in single file is advisable.


To reach Shelter Island, start at North Haven (a stone throw from Sag Harbor), where $6 buys a round-trip ticket for you and your bike on the South Ferry. The 5-minute cruise is a gem with views of Shelter Island Sound, a hint of sea breeze, the “thunk!” of the boat butting against tall wood pilings. Bicycles are last-on and last-off.

On the Shelter Island side, pull over at the wooden box that dispenses free maps on the right side of the road, just beyond the dock, or use the map included here on your smartphone.


Take Country Road 69 north heading for Big Ram Island. On your right, you’ll pass Mashomack Nature Preserve of the Nature Conservancy, a peninsula that comprises one-third of Shelter Island.

(Note: To shorten your Shelter Ride, you can skip the Ram Island leg that follows.)

Take a right onto Ram Island Drive, which loops around Big Ram Island. You’ll pass the gracious Ram's Head Inn and spy stunning waterfront homes interspersed with forested land.

A few short, heart-rate-boosting climbs lead to the Peconic Land Trust's 8-acre Reel Point park beach, where serene vistas of Coecles Harbor await.


After the Ram Island out-and-back, take a right and continue to the Village of Dering Harbor, where stately homes along Shore Road preside over the waterfront.

During the summer, elegant wood-paneled boats of the Adirondack-camp era are tied up at the docks while sailboats are moored in the harbor beyond.

After navigating the little bridge across Gardiners Creek, travel to the hamlet of Shelter Island Heights. The waterside village has a ferry for Greenport on the North Fork and the basic necessities: a hardware store, a gas station, restaurants, and Picozzi, on Bridge Road (technically 177 N. Ferry Rd.), the island’s only bike shop.

Picozzi offers bike repair and rentals year-around. Its fleet of Specialized bikes equipped with baskets start at $10 per hour.


Take a coffee break at the Stars Cafe, (17 Grand Avenue), a Shelter Island favorite for coffee and a snack. They also have a clean restroom! The colorful tables out front offer place to pause in the sun and watch over your bike. Up the block, browse breezy dresses and accessories with French flair at Marie Eiffel (8 Grand Avenue).


From there, travel south on Shore Road, where you'll find Sunset Beach (35 Shore Road), an Andre Balaz hotel and restaurant, where you’ll feel like a visitor to a European shore-front retreat. Enjoy a glass of wine or lunch on the upper deck and savor the water views. Don't miss the hotel boutique behind the bar.


To return to the ferry, loop back to South Ferry Road (Route 114), pausing at Marika Antiques (6 South Ferry Road) to survey funky antiques and at the Boltax Gallery (21 North Ferry Road) for selections of contemporary art.

For more Hamptons rides and cycling culture intel, visit Velojoy.com


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