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I fell under the spell of the Norwalk Islands early in life. My first dinghy, first fish, first outboard, first stranding, first (and only) dismasting and first island getaway — a camp that would have made Tom Sawyer and Huck Finn green with envy — all occurred in that enticing little archipelago. These Connecticut islands don’t rival Maine’s for brooding beauty, or the Caribbean’s for sun and sand. Yet their lure is undeniable.

When the glacier dealt shorelines, Norwalk drew a royal flush. It is only five miles from the eastern end of Cockenoe (kah-KEE-nee) Reef to Greens Ledge Lighthouse, but within that kingdom of islands, a world of wonders awaits. Beachcombing, birdwatching, paddling and piloting are just the start. There is fishing, of course, but there is also the presence of the past, which has an uncanny way of firing imaginations here. For centuries, these islands (20 of them, more or less) have been one of Long Island Sound’s great treasures, attracting pirates and preachers, fishermen and philanderers, dreamers and schemers.

At first glimpse, the chart plotter suggests that this stretch of Long Island Sound is anything but a boating paradise. With Hiding Rocks, Greens Ledge, Great Reef, Sheep Rocks, Haycock Rock, Cockenoe Shoal and Peck Ledge, the potential for running aground or dinging the prop seems limitless. More than one skipper and crew have found themselves high and dry at low tide, victims of the 6- to 8-foot swings. The water is thin for sure, but it’s eminently navigable by shoal-draft craft, or by those in deeper boats who pay attention.

The mystique emerges from the cheek-by-jowl assemblage of salt marshes, sandbars, oyster beds, rocks, channels, lighthouses and islands, one on top of the other and all of them constantly redefined by the angle of the sun, the state of the tide and your compass heading. Put another way, favorite places are endless, and they keep changing.

The eastern end of Sheffield Island boasts ruins of a Great Gatsby mansion, now nestled in a profusion of niche ecosystems. Part of the Stewart B. McKinney National Wildlife Refuge, that portion of Sheffield is not always open to the public because of protected bird habitat, but it’s worth exploring when you can. A trail from the old stone lighthouse at the western end will take you there. Or at high tide you can dinghy or paddle into the cove looking eastward toward Little Hammock, and savor it without going ashore.

Best of all, these islands are as accessible as they are charming. Most are less than a mile from shore. And access is not limited to locals. Twenty million people live within a one-hour drive of Long Island Sound. Manhattan is just 40 miles away. On clear days the skyline will be visible from your cockpit. If you don’t live locally, trailer your boat to the launch ramp in Veterans Memorial Park, where a modest fee provides access and adventure to all.

Want a challenge? Thread your way at low tide through the skinny channels separating Shea Island from Chimon and Copps islands. In midsummer, troll for big stripers along Greens Ledge, or hunker down to fish near the numerous mussel-laden ledges frequented by tautog in late spring and early summer. Alternatively, land on the northwest shore of Chimon Island — also part of the wildlife refuge — for a picnic or some birdwatching. If you stroll the eastern shore of Cockenoe at sunrise, you will feel like the only person in the world (even if there is a tug and tow in the offing, chugging down the sound).

Greens Ledge Light, built in 1902, guards the western end of the Norwalk Islands.

Though some of the islands are private, Shea and Grassy are owned by the city of Norwalk, and Cockenoe by the town of Westport. With others in the chain part of the wildlife refuge, there is plenty of public access. The little private islands, with their cottages and flagpoles, simply add to the view.

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Place names harken back to the days when Algonquians regularly paddled here. In 1690, Sagamore Winnipauk transferred “my island of land lying against Rowerton … bounded on ye east with ye island called Mamachimons and Chochaneas.” Rowayton, Chimon and Cockenoe are still on the tips of our tongues.

If the names have been stable, the islands have not. This is a dynamic shoreline. Two hundred years ago, Copps Island protruded 100 yards farther north than it does now, reaching a deep channel separating it from Crow Island, which in turn was separated from Chimon by another deep channel. But Copps was surrounded by smooth, round rocks, perfect for cobblestones. Coastal vessels heading for New York took loads of cobbles, destabilizing the shore. In 1845, a two-day storm radically altered the three islands’ contours. Much of Copps was washed away. Crow Island almost was leveled. The deep channels between the three were obliterated. You won’t find them today. The same wild storm created the sandy beach on Shea Island.

The infamous 1938 New England hurricane washed away nearly half of Grassy Island. Superstorm Sandy washed away other pieces of the islands’ past. The sands keep shifting, so the Army Corps of Engineers keeps dredging Norwalk Harbor’s entrance channel, and wise skippers keep a wary eye on their surroundings.

Part of the larger islands’ appeal now is their dense forest cover, a lush green canopy against the dark blue sea. Centuries ago, sailors simply saw fields and pastures. Capt. Robert Sheffield bought many of these islands in 1804, and by 1835, the first government survey map called the whole chain Sheffield’s Islands. Hardscrabble farming wore down the captain. His son-in-law, Gershom Burr Smith, farmed more productively, grazing cattle and horses on Chimon Island and sheep on Grassy. One occupational hazard? Balky cows. They regularly strayed at low tide, forcing Smith to row after them with milk buckets. Cows drowned every year. Without his lighthouse keeper’s salary, Smith might have gone under, too.

As teenagers, the author and friends slept aloft in nets they wove. This photo was taken by Daniel Moreland, one of the original campers, and now captain of Picton Castle.

His son Theodore operated a fish oil factory on Ram (now Shea) Island. Rendering menhaden oil was profitable, but it stank, and Theodore could interest no buyers in 1867 when he tried to sell his 10 islands — half of which were “in a high state of cultivation.” Ultimately, his heirs sold the islands in dribs and drabs. Though passenger steamers plied regular routes in the late 1800s, and a fleet of oyster sloops dredged the bountiful shallows, recreational boating was still virtually unknown.

By the Roaring ’20s it was clear the islands were more suited to fun than work. A Manhattan architect named Alfred Mestre built the estate on Sheffield. Disembarking from fantail launches, his elegantly attired guests landed on a long pier capped by a bold granite gazebo. A flagstone walkway, surrounded by delicate gardens and shaded by a roof on stone pillars, led them through a terrace to the gracious stucco house with panoramic views. Balky cows and the smelly oil factory were history.

But the fun was just beginning. In 1923, an industrial chemist at Fleischmann’s Yeast, who had as many girlfriends as patents (and plenty of each), bought Mestre’s estate. Recently divorced and ready to party, Robert L. Corby built a golf course that doubled as an airstrip for small planes, along with tennis courts and stables for polo ponies. Guests caught the launch from Gene’s Boat Livery in Rowayton or arrived in style aboard their own yachts. Though alcohol was illegal nationwide, European royalty clinked glasses with Manhattan socialites. Starlets danced with tycoons. On summer evenings, the mansion’s illumination and partygoers’ raucous laughter drifted across the channel. Locals in powerboats gawked at the spectacle.

The Great Depression spoiled the fun. Vandals began to wreck the place. More buildings burned, and after several false starts at development, Sheffield reverted to nature.

Twenty years after Corby’s last bash, Broadway producer and lyricist Billy Rose bought tiny Tavern Island, just inshore from Sheffield. His fabulous parties included celebrity guests such as Marilyn Monroe. Once a small farm and base for Long Island Sound pilots, Tavern Island, with its Tudor-style home, remained Rose’s enchanted estate until his death in 1966. Numerous statues adorned the manicured grounds. The wacky Rose married five times, and friends claimed that following each divorce, he decapitated another statue.

By the 1960s, little islands such as Tavern, Copps, Wood and Sprite remained in private hands, but the big ones were going native. Absentee owners ignored them. Boaters, duck hunters and campers moved in. When United Illuminating Co. bought Cockenoe Island in 1966 for a nuclear power plant site, public outrage erupted. Conservationists persuaded the town of Westport to buy the island and encourage public access. So during the middle of the 20th century, the islands were redefined from Roaring ’20s opulence into wilderness worth preserving. Rachel Carson would have been pleased.

Prior to 1900, few pleasure boats came to the islands, but a fleet of sailing dredges worked the oyster beds.

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My cameo role in this enchanted story began in the ’60s with high school friends from Rowayton. An old wooden skiff with its occasionally reliable Evinrude made the islands ours. From Wilson Cove, it was just a mile to the pier at Sheffield, and it wasn’t long before we had convinced our parents that camping out on “the island,” as we called it, would be fine.

A hundred yards inland from the ruined mansion, a majestic sugar maple shaded a forest clearing. We scrounged cut stones from the ruins for our fireplace, driftwood timbers from the beach for a table and, most essentially, castaway tugboat hawsers from the rocky south coast. Unraveling them provided long poly-pro strands. We intended to sleep aloft: That meant weaving nets in a tree. Robinson Crusoe could not have been more proud. Lulled to sleep by wind and wave, with the fire’s dying embers far below, surrounded by nature and the ghosts of the past, we were enchanted island kings. No one in Maine or the Caribbean had it better.

But we weren’t the only long-haired teenagers with camps on the island. Rumors spread that “communes” were taking root where starlets and polo ponies once roamed. On May 30, 1970, the Norwalk police raided Sheffield and arrested 32 people, charging many with possession of marijuana. My friends and I avoided the bust. We convinced our parents that our camp was totally squared away, and we continued to use it for years. Our Thanksgiving feasts, entertaining 30 or 40 kids each, became legendary.

In those days, I could run full tilt through the darkest night without a flashlight in sight — from the pier to the overgrown terrace, past the pillars, through the mansion’s spooky ruins and across the roots and rocks from the tumbled-down estate to the trail and camp beyond. I knew every inch. Every rushed step brought a moment of immortality.

Ten years ago, my chief co-conspirator from “the island” anchored off Sheffield en route from Baltimore to Newport, via New York City. That would be Capt. Daniel Moreland, with his 300-ton barque, Picton Castle. He emailed: “Thought I would show the gang a cool place. … Turns out the island is a federal wildlife preserve now. … A guy comes around to tell us we cannot just do what we want on Sheffield. But he is the caretaker of the lighthouse at the west end, and he invites us to come hang out there, which we do. Sweet time. Bonfire on the rocky south beach. Music and singing. Then buddy tells me of these legendary kids who lived out on the island in nets in the trees. Then his buddy, caretaker of Tavern Island, joined us too, and they went on about those kids in the trees and how those were the days. Yes, they were. I revealed my true identity as one of those island kids. If I told him I was Mick Jagger’s brother, I do not think it would have been any more impressive. Anyway, we ended up having a sweet, edacious, island night.”

Sunrise over Tavern Island, 2016, from a guest mooring at the Norwalk Yacht Club.

There’s been magic in the Norwalk Islands for centuries. It keeps changing, but it never stops.

This article originally appeared in the July 2017 issue.



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