SAIL NEW ENGLAND - The Connecticut Shoreline

Routes into Long Island Sound

There are three alternative routes into Long Island Sound when approaching from Block Island Sound.

The northernmost passes Watch Hill, RI, and runs through Fishers Island Sound where the Connecticut Shoreline destinations await.

But just before entering Connecticut proper, there is one final destination in Rhode Island that attracts many visiting and local yachtsmen - Watch Hill.

Just off the town is the snug enclosure of Watch Hill Cove with a wider natural harbor beyond, bordered on the south by the length of sandy Napatree Spit.

Ashore Watch Hill is in some respects a miniature version of glittering Newport, with a listed historic district and expensive mansions on the bluff overlooking Block Island Sound.

Flying Horse Carousel

Watch Hill also has the Flying Horse Carousel, claimed to be the oldest in the US and part of a traveling carnival until 1879 when the carnival was forced to abandon the carousel in Watch Hill.

Unlike most carousels, there is no wooden platform to support the horses but rather they are suspended from chains and so the horses seem to "fly" as the ride increases speed. Each horse has a tail and mane of real horsehair and a genuine leather saddle.

Leaving Watch Hill and entering Connecticut, immediately to starboard is the peninsula on which Stonington sits, offering a convenient sheltered anchorage and historic buildings ashore.

Mystic Seaport

Only five miles to the east of Stonington and a short run up Mystic River lies the village of Mystic and the renowned Mystic Seaport, housing the nation's largest maritime museum.

Mystic Seaport has preserved, and displays afloat, a number of sailing ships most notably the whaling ship Charles W. Morgan, the only surviving wooden sailing whaler.

The seaport itself is made up of a collection of more than 60 original buildings which have been fully restored to working order and laid out on the 37 acre site to reconstruct a 19th century seafaring village. Craftsmen work on site using traditional tools and techniques to show how a seaport such as this would have operated 150 years ago.

Mystic Seaport waterfront

Also in Mystic is the Mystic Aquarium & Institute for Exploration, one of only four facilities nationwide where people can see Steller sea lions and it has one of the largest outdoor Beluga Whale exhibits in the US. Other exhibits include a ray and shark touch pool, a penguin exhibit, and a jelly gallery.

The Institute for Exploration features maps, diagrams, and models from Dr Robert Ballard's explorations of the Black Sea and of the wreck of the RMS Titanic.

Back on Long Island Sound, just a few miles further east is the major port of New London, sitting at the mouth of the Thames River. New London used to be considered the best deepwater harbor on Long Island Sound and historically was both a major whaling port and naval base. Today the city is is home to the US Coast Guard Academy and home port to the USCG cutter Chinook and the USCG tall ship Eagle.

Nautilus submarine

On the east side of the river opposite New London is Groton with its US Navy submarine base and home of the Electric Boat Company, the major contractor for submarine work for the US Navy, so submarines can often be seen tied up to the docks beside the river.

Here is also the Submarine Force Museum with the historic submarine Nautilus on display. Launched in 1954, Nautilus was the world's first nuclear powered vessel and the first ship to go to the North Pole.

4th July fireworks

If ever you are near New London around 4th July weekend, the firework display is quite unmatched, especially when viewed from the ringside seat offered by an anchored yacht...

Next stop a few miles further east is The Connecticut River, the largest and longest river in New England at over 400 miles long.

The first significant settlement upstream (passing Old Saybrook at the mouth of the river) is the town of Essex, tucked into an idyllic spot on a bend in the river.

Essex was historically famous as a shipbuilding center (Connecticut's first warship, the Oliver Cromwell, being built there) and this was the reason for the British attack on the town during the War of 1812 when they destroyed 28 vessels that were ready or nearly ready for sail.

The Griswold Inn

The town retains much of its historic appeal in the historic architecture lining Main Street, at the bottom of which is The Griswold Inn (known locally as the "Gris"), the oldest continuously-run tavern in the US.

Essex steam train

Essex also has a steam train railway and station from which passengers can travel 12 miles in vintage coaches into the heart of the Connecticut River Valley up to Deep River Landing where they can join a riverboat for a cruise further up the Connecticut River, or can connect with a ferry to visit Gillette Castle.

Pilots Point Marina Westbrook

Back on Long Island Sound, heading east from the mouth of the Connecticut River, staying in the calm water just inside inside Long Sand Shoal, you are invited to take a break from your cruise along the Connecticut Shoreline and drop the hook in the protected anchorage of Duck Island Roads.

Come to our docks at Westbrook's Pilots Point North marina where you can expect a warm welcome - at both the marina and our office.

Continuing west from our base in Westbrook, there are many destinations for the cruising sailor but in the limited space of this web page we will stop at only a couple of these.

Thimble Islands

Sailing past Clinton and Guilford, with Falkner Island to port, we next come to the Thimble Islands, an archipelago of islands made of Stony Creek pink granite bedrock that were once the tops of hills prior to the last ice age, looking now almost as if a little bit of Maine has been scattered here.

Oyster farming was a thriving industry in the nineteenth century but the Thimble Islands are now enjoyed primarily as a sunbathing spot for seals and a welcome summer anchorage for boaters.

Sailing on past Branford, the commercial port of New Haven (home port of a life-size replica of the freedom schooner, Amistad, built at Mystic Seaport), Stratford, Bridgeport and Fairfield, our next stop is Norwalk and its off lying islands.

The farming of oysters has long been important to Norwalk, with production reaching a peak in the 1890s when it proudly possessed the largest fleet of steam-powered oyster boats in the world. Norwalk was once nicknamed "Oyster Town" and in September each year holds an Oyster Festival.

Norwalk oyster boat

Cruising among the off lying islands, the oyster beds are much in evidence from their markers and the oyster fishermen diligently working them.

Ashore, the Norwalk Maritime Aquarium focuses specifically on the marine life of long Island Sound. The aquarium is at the center of the South Norwalk (SoNo) area of shops, boutiques, restaurants and cinemas and itself features an IMAX theater.

From Norwalk, the Connecticut shoreline all the way west to the border with New York offers many indentations and sheltered coves to explore - Rowayton, Noroton, Darien - as well as a number of larger protected harbors such as Stamford.

Manhattan skyline

By the time you pass Cos Cob and Greenwich and reach the Connecticut/New York state line, Long Island Sound will have narrowed to only 6 miles and the skyline of Manhattan will have been visible ahead of you for many miles.

Statue of Liberty

Only a couple of hours sailing from here will take you down the East River, past the glass walls of the skyscrapers of the city and out into New York Harbor, the Statue of Liberty gazing serenely over this busy waterway.

And seeing the Statue of Liberty from the water is the only way to really appreciate it.


Throughout New England, especially along the Connecticut Shoreline, there are many marinas offering first class accommodation and support for the cruising sailor.

Follow this New Boat Shakedown link to see why we think this provides an unrivalled opportunity to cruise New England as initial preparation for heading to all points south.

For a more personalized itinerary for the cruising grounds of the Connecticut Shoreline, please contact us.

Click this link to go back to "Destinations"

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