The islands in our midst

A commercial fishing boat on a pier at Ram Island, just outside the mouth of the Mystic River. Photo by Sue Cornell

By Susan Cornell
For Points East

On a weeklong Long Island Sound cruise last summer, it dawned on my husband Bob that the common theme during it was the islands in the sound, along the New York and Connecticut shores. With our valiant explorer Bailey – a 15-pound Puggle (a pug/beagle crossbreed) – aboard our Nonsuch Halcyon, we sailed from Safe Harbor (SH) Pilots Point, in Westbrook, Conn., to SH Stirling in Greenport, N.Y. We cruised in company with friends on their Nonsuch Ardent, for a two-night stay at our first destination. While Greenport is not an island, we couldn’t pass up those “10 FREE Transient Nights at Any Safe Harbor Marinas property.”

Now Greenport is fun – outdoor concerts, wineries, zillions of restaurants, interesting architecture, and hiking in a nature preserve – but we needed something new and different. Assuming the answer would be a definitive “No,” I emailed Shelter Island Kayak before departure and inquired about renting kayaks with our “small, friendly, well-behaved, well-traveled, and very experienced kayaking pup.” The reply was a definitive “YES.”

The walk from the marina to the Shelter Island Ferry was roughly a mile and a half, after which a two-dollar ferry delivered us to elegant and exclusive Shelter Island. If we hadn’t had our pup that hot day, we would have walked the three miles to the kayak launch. The walk would have been lovely, particularly with a stop for competitive miniature golf. However, the Shelter Island version of Uber, Go’fors Taxi, was reliable, cheap ($14), and air-conditioned. Shelter Island Kayak is a simple operation: a Jeep situated at the end of a road, with a bunch of kayaks, PFDs, water and granola bars.

The selling point for renting kayaks, as opposed to bringing our own (which we pre-staged in Mystic before departure), was that Shelter Island Kayak is perfectly situated on the Coecles Harbor Marine Water Trail, a 7.4-mile sea-kayaking trail. This is a joint project of Shelter Island Kayak tours, The Nature Conservancy, and the Town of Shelter Island. Kayaking from Stirling to Coecles Harbor was out of the question, due to large boat wakes along the route and the round-trip distance.

The Water Trail offers an easy way to explore the natural beauty of Shelter’s calm, protected creeks and harbors, in which you’ll see ospreys, hawks, egrets, turtles, and, perhaps, foxes by their dens. One of the highlights of kayaking was right in Coecles Harbor’s Taylor’s Island, site of the historic Smith-Taylor Cabin. The cabin is listed on the New York State Register of Historic Places, and it is free to the public.

Francis Marion “Borax” Smith bought Cedar Island in 1899 to expand his Shelter Island summer estate, known as Presdeleau. For decades, his Pacific Coast Borax Company, marketed as “20 Mule Team Borax,” was the industry leader. Borax Smith built the log structure on Taylor’s Island as a retreat for picnicking, clambakes and entertainment.

Taylor’s Island and the Smith-Taylor Cabin are cool places to hang out, lazing in Adirondack chairs, picnicking, catching the breeze, and oohing and aahing at the panoramic views. Plus, there’s that triple-island thing: Taylor’s Island is within Shelter Island, which is on Long Island.

The second of the two highlights was Coecles Harbor Marina & Boatyard, famous for building Billy Joel’s 38-foot Shelter Island Runabout. Not a bad design considering it started with sketches drawn on cocktail napkins, and was enhanced by the skills of naval architect Doug Zurn. Allow about three to four hours to kayak the Coecles Harbor Water Trail.

Next year, we will moor in Coecles Harbor, and hop right into our own kayaks. One tasty option is to pick up a mooring at Ram’s Head Inn, on Ram Island, where, as long as you dine at the restaurant, the mooring is free (at least at the time of this writing). Ram’s Head has seven moorings, no reservations, first-come, first-served.

For the Greenport shopper, a must-see is the famous Preston’s Chandlery. This 139-year-old business supplied the local shipyards with whatever they needed to maintain the vessels that came into Greenport for service. Among notables were yachts owned by the Vanderbilt family and the J Class yachts that raced for, and won, the America’s Cup.

When it came time to leave Greenport, Halcyon and Ardent sailed from Greenport to Mystic, with a navigator’s choice along the way. Halcyon opted to go through Plum Gut, between Orient Point and Plum Island, while Ardent went through The Race, just off the western extremity of Fishers Island. We had a great view of the west and north sides of Plum Island, while Ardent saw more of the south side of the island and Little Gull Island.

This view of Plum Island was completely new for us, and clearly revealed the Animal Disease Center, which, over the years, because of its isolation and brooding appearance, has spawned bizarre and unsubstantiated rumors about strange experimentation on both humans and animals.

On that particular day, it took us roughly four and a half hours to get from Greenport to Mystic; currents and wind angles favored the passage through Plum Gut. Our reward? Pizza and beer, seating outside with our pup, at Pizzetta’s in Mystic. The next three nights were spent at SH Mystic. Our own kayaks were there waiting for us, although rental kayaks and SUPS are readily available on the Mystic River. Having planned numerous sunrise and sunset kayak adventures, we went the BYO route.

On our first trip, we were bound north, under the Mystic River Railroad Bridge (aka “the swing bridge”), and then under the Mystic River Bascule Bridge (aka “the Mystic drawbridge), and into Mystic Seaport. So many kayaks, so many SUPs: This was not at all the natural beauty of Shelter Harbor, but it was so much fun. Plus, we usually visit Mystic Seaport by car, as on-land tourists. Kayaking gives us a different perspective of such vessels as the Whaleship Charles W. Morgan, the working catboat Breck Marshall, the auxiliary schooner Brilliant, the steamboat Sabino, and, when we were there, the Mayflower II restoration.

Transported by our 10-foot cockleshells, we attended the 34th annual Moby Dick Marathon onboard the Morgan. This 24-hour reading of “Moby Dick” aloud is the longest running marathon read in the country and celebrates the 200th birthday of Herman Melville, the author of this classic American novel.

The second trip, at sunrise the following morning, we went south, counterclockwise around Mason Island, Ram Island, and Enders Island, then back to the marina. This journey, totaling seven miles of kayaking and a half-mile of walking on Enders Island, took about three and a half hours and, importantly, added three more islands to our life list.

Ram Island is a 20-acre island about a mile offshore, between Mystic and Fishers Island. It appeared to consist of a trailer home, horse, docks, and active construction equipment. Ram Island, once known as Mystic Island, was formerly the site of a ritzy hotel resort where steamships from Boston and the Big Apple stopped. The hotel hosted a world lightweight, bare-knuckle, boxing championship, but it fell into disrepair in the 1920s.

The New England Hurricane of 1938 completely destroyed the hotel. Later, a new motel that catered to transient boaters was built on Ram Island. Then it served as a private residence and farm since 1978, but fires in February 2013 and March 2014 destroyed the home and barn. Inexplicably, a lone horse remains.

A few paddle strokes back upriver took us to Enders Island, which is attached to Mason Island by a causeway. A small beach there is perfect for a kayak landing. The sole inhabitants of Enders Island operate a retreat center and art school owned by the Catholic Society of Saint Edmund. All these years sailing past, we knew neither of its purpose or beauty. Enders Island is open to the public, with a chapel, surrounding views of the Atlantic, and walking paths with amazing flower gardens. It’s even dog friendly!

The island was purchased from the Sisters of Charity by Dr. Thomas B. Enders, the son of the president of Aetna Insurance Company, and, in 1918, he and his wife, Alys VanGilder Enders, designed the private estate with a grand main house. The grounds still feature their imported Italian tiles in the garden and house, and a surrounding wall of large boulders that serves as a windbreak.

Mrs. Enders willed the island to the Society of St. Edmund before her death in 1954, requesting that it be used as a retreat and place of spiritual training for priests in the diocese. In 2003, an independent ministry was established on the island. Enders Island offers private retreats and an array of programs open to people of all faiths as well as recovery ministry for college-aged men.

We continued our circumnavigation of the three islands, passing the eastern shore of Mason Island as we made our way back to the marina. Mason Island was named after Major John Mason, who was granted the island in recognition for his military services in the 1637 Pequot War in Mystic. This island remained in the Mason family from 1651 to 1913 – that’s over 250 years. Mystic River Marina and Mason’s Island Marina are located on the island’s north end. The beautiful Mason’s Island Yacht Club is on the eastern side.

We’d passed by Mason, Ram and Enders islands for many years, and we never stopped to observe the details – the flowers, the architecture, the remains of the past – or read about the history. We’d been so busy getting to our destination, putting on the sail cover, putting out the fenders, and perhaps planning happy hour that we seemed to have forgotten the cool stuff off the beaten path, places in our own state we’d never appreciated.

Back in the town in Mystic, a must-see is Mystic Nautical Marine Consignment. Just down the street from Mystic Seaport, the shop specializes in traditional boating hardware, nautical antiques and art, and everyday boating necessities. The merchandise is fun to check out, and the prices are great. And you’ll probably find yourself a seller here, as you mentally dust off the unused items in your basement.

Halcyon and Ardent shoved off at sunrise and sailed back to our homeport of Westbrook – an uneventful and beautiful sail all the way. The islands of French Polynesia and the Caribbean may be the dream of many cruisers, but Long Island Sound really offers so much – especially in the form of islands – right here in our own backyard.

A resident of Killingworth, Conn., Susan Cornell is an independently contracted writer, photographer, and marketing and public relations consultant. During the summer, she and her husband Bob sail Southern New England waters aboard their Nonsuch 30C Halcyon.