Long Island Sound: New York's Backyard

Destination Guide · Long Island Sound

Long Island Sound is 110 miles long, as much as 21 miles wide at its broadest, and sheltered from open-ocean swell by Long Island's 100-mile spine to the south. Those numbers make it one of the most densely sailed bodies of water in the world — the combined boating populations of New York City, the Hudson Valley, Connecticut, and Rhode Island all pour into it. On a summer weekend, you will not feel alone. But the Sound rewards commitment: sail it with attention to its particular geography and rhythms, and it pays back with some of the best coastal cruising in the Northeast.

The basic polarity of the Sound is well known to anyone who has sailed it. Connecticut has the better harbors. Long Island has the better beaches. Connecticut's north shore delivers Mystic, Essex, Stonington, Old Saybrook, and a string of river mouths and protected anchorages that have attracted recreational sailors since the 1800s. Long Island's north shore has shallower approaches, sandier bottoms, and the summer-afternoon offshore breeze that makes Cold Spring Harbor, Port Jefferson, and Oyster Bay attractive in their own right — but the deep-draft cruiser will spend more time on the Connecticut shore.

Mystic, CT: The Living Museum

Mystic Seaport Museum is the argument for making the eastern Sound a destination rather than a waypoint. The museum is a reconstructed 19th-century maritime village, and its collection of historic vessels includes the Charles W. Morgan, the last surviving wooden whaleship from the American fleet, launched in 1841 and still afloat. The Joseph Conrad is also there — a Danish full-rigged ship that served as a training vessel. These are not replicas. They are the ships themselves, and arriving at Mystic Seaport by water, as sailors did for 150 years, is the correct way to arrive.

Boats arriving by water dock at the Cove marina, immediately adjacent to the museum grounds. The approach up the Mystic River from the Sound passes through a bascule drawbridge that opens on signal during daylight hours — call on VHF Ch 13. The town of Mystic itself clusters along both banks of the river: restaurants, chandleries, and the tourist infrastructure that accumulates around a working maritime destination. Allow two days minimum. The museum alone is a full day.

Essex, CT: The Best Small Boating Town in America

Essex has been called the best small boating town in America so many times the claim has nearly become cliché — except that boats keep arriving and the town keeps deserving it. Essex sits four miles up the Connecticut River from the Sound, and the approach on a summer morning, with the marshes opening up on both sides and the white steeples of the town coming into view, is one of the pleasures of the Sound. The Connecticut River is the longest river in New England, and Essex sits at the point where the tidal portion reaches maximum charm.

The Griswold Inn, on Main Street since 1776, is the institutional anchor of Essex — its taproom is one of the oldest continuously operating taverns in America, and the Sunday Hunt Breakfast is a local institution that deserves an overnight stay to justify it. The Saturday morning farmers' market runs from May through October two blocks from the town dock. The Essex Island Marina is the largest facility in town; the Connecticut River Museum, on the waterfront, covers the maritime history of the river in a way that rewards the half-day it takes. Transient dockage at Essex fills up on summer weekends — call ahead.

Stonington, CT: The Last Fishing Village

Stonington Borough, at the eastern end of the Connecticut shore, is the last active commercial fishing village on the Connecticut coast. The fleet is small and working — draggers and lobster boats — and the harbor entrance between the breakwaters feels utilitarian in a way that Essex and Mystic do not. That is the attraction. Stonington has not been entirely retrofitted for visitors, and the Portuguese fishing community that has worked these waters for generations gives the town a character distinct from the yacht-club culture that dominates so much of the Sound.

Anchor east of the breakwater in settled weather, or take a berth at the Dodson Boatyard if one is available. The town has good provisioning for its size, a few restaurants worth the walk, and the kind of quiet that expensive harbors have stopped being able to provide. In summer it fills with sailboats anyway, because the word is out, but arrive midweek and you will still find space.

The Race and Plum Gut

The eastern Sound has two exits: the Race and Plum Gut. Both are tidal passages that deserve respect. The Race is the main channel between the eastern tip of Fishers Island and Little Gull Island — roughly half a mile wide, with currents that run 3 to 5 knots on a strong tide. When the tide is running against a southwest wind, the chop in the Race is short, steep, and relentless. Time the Race for a fair tide, which means knowing the tidal tables for the Race rather than for Block Island or the Sound — the timing differs by an hour or more depending on your reference point.

Plum Gut is the narrower channel between Plum Island and Orient Point at the northeastern tip of Long Island, with currents reaching 4 to 6 knots on a strong moon. Plum Gut is shorter but faster — the current accelerates through the constriction in a way that produces standing waves at maximum flood and ebb. Boats have been caught there in rough conditions. The ferry between New London and Orient Point transits Plum Gut regardless of conditions; give it room. The timing window for a comfortable Plum Gut transit is narrower than the Race, but the route is shorter for boats heading for the North Fork of Long Island or the Peconic Bay system.

Hell Gate: The Western Entrance

The western end of Long Island Sound connects to New York Harbor via the East River, and the East River contains Hell Gate — the confluence of the East River, the Harlem River, and the tidal flows from the Sound that produces one of the most turbulent pieces of water on the American coast. Currents in Hell Gate run 3 to 5 knots at strength, and at maximum ebb or flood in a strong wind the surface is chaotic in ways that are unpleasant in a small boat.

Most sailboats bound for the western Sound from the south go around Long Island — offshore from Sandy Hook to Montauk and into the Sound from the east — rather than through Hell Gate and the East River. The East River route is faster in miles but requires favorable tides for Hell Gate, careful attention to commercial traffic in one of the busiest waterways in the Northeast, and navigation in water where the buoys are close together and the ferries do not slow down. Experienced local boats do it routinely. A sailboat coming from south of New Jersey, making the run to the Connecticut coast for the first time, is better served going around the end.

The Racing Scene

The Sound has an active racing culture that predates most of the institutions that govern it. The Vineyard Race — officially the Newport Bermuda Race's shorter cousin, organized by the Storm Trysail Club — starts in the Sound each summer and finishes off Martha's Vineyard. The PHRF fleets out of Greenwich, Stamford, Larchmont, and New Haven run regular Wednesday-night and weekend series from May through September. One-design clubs from Greenwich east to New Haven field fleets of J/24s, Lightnings, Comet 15s, and the various handicap classes that have always found the Sound's predictable summer southwesterlies ideal for racing.

The summer afternoon sea breeze — southwest at 10 to 18 knots, filling in by 1300 most days from June through August — is the Sound's defining sailing condition. It is reliable enough that racing schedules are built around it, and consistent enough that a newcomer to the Sound can learn to trust it. The same sea breeze that makes the Sound excellent for afternoon racing makes the morning return trip from an overnight stop a motorsail in the calm and the afternoon return a beat against the incoming breeze — which, depending on your departure point, is either the charm or the annoyance of sailing the Sound.

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Frequently Asked Questions

Why does Long Island Sound's geography favour the Connecticut shore over Long Island for deep-draft cruisers? Connecticut's north shore delivers Mystic, Essex, Stonington, Old Saybrook, and a string of river mouths and protected anchorages that have attracted recreational sailors since the 1800s. Long Island's north shore has shallower approaches and sandier bottoms. The article states directly: 'the deep-draft cruiser will spend more time on the Connecticut shore,' while noting Long Island's north shore has beaches and an offshore afternoon breeze that attract smaller boats.

What historic vessels can be seen at Mystic Seaport Museum and how should sailors arrive? Mystic Seaport Museum's collection includes the Charles W. Morgan, the last surviving wooden whaleship from the American fleet, launched in 1841 and still afloat, and the Joseph Conrad, a Danish full-rigged training ship. These are not replicas — they are the original ships. Boats arriving by water dock at the Cove marina immediately adjacent to the museum grounds via the Mystic River, passing through a bascule drawbridge that opens on signal on VHF Ch 13.

What makes the Race and Plum Gut the two key tidal passages at the eastern end of Long Island Sound? The Race between Fishers Island and Little Gull Island has currents running 3 to 5 knots; when tide runs against a southwest wind, the chop is short, steep, and relentless. Plum Gut between Plum Island and Orient Point reaches 4 to 6 knots with standing waves at maximum flood and ebb. Timing requires the specific tidal tables for each passage — the Race timing differs by an hour or more from Block Island references. Plum Gut's transit window is narrower than the Race.

Why do most sailboats avoid Hell Gate when entering Long Island Sound from the west? Hell Gate — the confluence of the East River, Harlem River, and Sound tidal flows — runs 3 to 5 knots at strength, and at maximum ebb or flood in strong wind the surface is chaotic in ways 'unpleasant in a small boat.' The East River route requires favourable tides, careful attention to commercial traffic, and navigation where 'the buoys are close together and the ferries do not slow down.' Most sailboats from south of New Jersey go around Long Island's eastern end instead.

What is the summer afternoon sea breeze on Long Island Sound and how does it shape sailing there? The summer afternoon sea breeze fills in from the southwest at 10 to 18 knots by 1300 most days from June through August, and is reliable enough that racing schedules are built around it. It makes the Sound excellent for afternoon racing but means morning return trips from overnight stops are a motorsail in the calm, and afternoon returns are a beat against the incoming breeze — 'which, depending on your departure point, is either the charm or the annoyance of sailing the Sound.'

What distinguishes Stonington, CT from the other Connecticut Sound harbours? Stonington Borough is the last active commercial fishing village on the Connecticut coast with a working fleet of draggers and lobster boats, and a Portuguese fishing community that has worked these waters for generations. The harbour entrance 'feels utilitarian in a way that Essex and Mystic do not.' It has not been entirely retrofitted for visitors, offering the kind of quiet that expensive harbours have stopped providing — though it fills with sailboats in summer because the word is out.