The only way to get to Shelter Island is by boat, and when you take the North Ferry from Greenport, your voyage is 10 glorious minutes of salty air, sailboats, seabirds and charming Victorian cottages. With that kind of introduction, it’s easy to imagine the ferry is taking you back to an earlier time.
Roll off the ferry on a bike, instead of a car, and you transform your visit to this beautiful and sometimes quirky place into a real tour — not a drive-by. The pace of Shelter Island is slow and has been since the Manhanset Indians spent their summers living off the island’s land and bays more than a thousand years ago.
The excellent (and free) map of Shelter Island — available at the North Ferry office — shows all 8,000 acres of this seven-mile-wide island, about a third of which is composed of the Mashomack Nature Preserve. Consider this 10-mile bike route a starting point for further exploration.
Follow Route 114 off the ferry, up the hill and into the heart of “The Heights,” a Victorian-era resort community of gingerbread cottages, a beach club and a chapel conceived as a Methodist retreat. You’ll pass The Chequit, which was the restaurant for the Methodist camp and is now a stylish boutique hotel.
Continue on Route 114, turning left to cross the first of the island’s two tiny bridges, into the shops of Bridge Street. It still looks a lot like it did in the 19th century, except for its rustic archway and unpaved road.
If you haven’t already made provisions for lunch, this would be a good time to stop at Marie Eiffel Market across from the gas station for a sandwich or salad to go, or to eat at the outdoor tables. Her baguettes are home-baked, with a wonderful crust and pleasant chewiness.
Back on Route 114, climb up the hill from Bridge Street and continue about a mile to the white stone gates on the left of Sylvester Manor, where sugar merchant Nathaniel Sylvester established a plantation in 1651.
Continue straight onto Manwaring Road and look toward your left for the windmill, which was built in 1810 to replace an even older one that burned down.
Take the first left at the traffic circle onto Ram Island Road. Formerly known as Factory Road, it once led to the Menhaden Fish Factories, which sustained the economic health of Shelter Island in the 19th century. Menhaden, also known as bunker, is a tiny, oily fish that was cooked down in large cauldrons and used for fuel and fertilizer and for tarring nets.
Ram Island Road becomes Gardiner’s Bay Road and a right turn on Menhaden Lane leads to Hay Beach, one of the loveliest beaches on the island. The only oily things cooking on the sands these days are the sunbathers.
Ride back up Menhaden Lane and left on Gardiners Bay Road.
A left turn on Ram Island Drive leads you to Little Ram and Big Ram islands, which were linked by a causeway leading to the rest of Shelter Island in the early 20th century. Many of the telephone poles on the causeway out to Little Ram Island are topped with osprey nests. If you keep a respectful distance you may observe these large birds catching fish well above the size limit, feeding young ospreys the size of turkeys and otherwise going about their business.
Approximately five miles from the ferry you’ll reach the halfway point on the right: the Ram’s Head Inn, a beautiful inn and restaurant perched on a hill above Coecles Harbor. The expansive hammock and chair-strewn lawn is a great place to have a drink.
Turn left out of the Ram’s Head to return to Ram Island Drive and the views on your right are of Gardiners Bay, with “Bug Light” lighthouse to the north, which looks like an insect perched on the water off the shores of Orient.
Turn left on Ram Island Road and then right on Cobbetts Lane, which curves up and flattens out into a line of old oaks and maples. The white oak on the right, just past Overlook Place, is thought to be about 150 years old. These trees are a reminder of the importance of island timber to the barrel construction that was central to transporting goods by ship, which is said to be the reason Nathaniel Sylvester bought Shelter Island in the first place.
Turn right on Manhanset Road and ride through a flat area of dense woods, shady and cool. Where the woods end an enormous beech hedge — planted 75 years ago by LaVerne Hench, and one of only two on the eastern end of Long Island — welcomes you to the hamlet of Dering Harbor.
Follow Manhanset onto Locust Point Road. Turn right on Yoko and then left on Shore Road past a row of impressive mansions looking out on Dering Harbor.
Follow Shore Road as it turns into Winthrop and over a second bridge (known by the straightforward local people as “Second Bridge”), where you can pause, look to your left, and see a lovely inlet (or “creek” as it is known around these parts).
This is the ancient heart of Shelter Island, where Manhanset tribes established a village. Just beyond that is the spot Nathaniel Sylvester chose to build Manor House in 1651. To your right is Dering Harbor, with views north to Greenport.
Continue on Winthrop to North Ferry Road, aka Route 114, where a right turn takes you back through Bridge Street to the North Ferry.
A boat is the only way to get to this island, and a boat is the only way off, so time your departure for sundown, head to the west side of the ferry and enjoy the show.