North by Northeast: A Montauk Sailor's Guide to Cruising Connecticut and Rhode Island's Hidden Harbors

The Itch Every Montauk Sailor Eventually Gets

There's a moment that happens to almost every sailor based out of Montauk. You've done the run to Block Island a dozen times. You know where the current rips around Montauk Point, you've anchored in Coecles Harbor, and you can practically navigate to Three Mile Harbor in your sleep. And then one afternoon, standing on the dock with a decent westerly building behind you, you find yourself squinting north — past the Race, past the Connecticut shoreline — and wondering what's up there.

The answer, according to plenty of local sailors who've made the jump, is a lot. Connecticut and Rhode Island's coastlines are loaded with quiet harbors, working fishing towns, and tucked-away anchorages that most cruisers simply blow past on their way to somewhere else. If you're sailing out of Montauk and you've been thinking about extending your range, here's a practical look at what's out there and how to get there.

Getting There: Reading the Race

Before anything else, let's talk about the passage itself. The stretch of water between Montauk and the Connecticut coast isn't particularly long — you're looking at roughly 15 to 25 nautical miles depending on your destination — but it runs through some genuinely demanding water.

Fisher's Island Sound and The Race, the deep-water channel between Fisher's Island and the Connecticut coast, are famous for strong tidal currents that can run three to five knots on a big tide. Time it wrong and you're essentially sailing in place. Time it right and the current becomes your best crew member, pushing you along at hull speed without burning a drop of diesel.

The local rule of thumb: aim to arrive at The Race near slack water, which happens roughly six hours after high tide at New London. Cross during the ebb if you're heading east toward Rhode Island, and use the flood if you're working west toward the Connecticut River. The NOAA tidal current charts for the area are worth downloading before you leave the dock — don't just rely on your phone signal out there.

Weather-wise, the prevailing summer southwesterlies make for a comfortable beat heading north, and a sweet broad reach coming home. Fall tends to bring stronger and more variable winds, but the crowds disappear entirely and the anchorages feel like they're yours alone.

Connecticut's Secret Coastline

Mystic, Connecticut gets most of the attention — and for good reason. The historic seaport, the working drawbridge, the smell of salt and old wood — it's genuinely worth a stop. But Mystic can get crowded in summer, and the approach up the Mystic River requires patience and a shallow draft or careful attention to your keel. Call ahead to Mystic Seaport's dockage or plan to anchor in the outer harbor and dinghy in.

For something quieter, Noank sits just southwest of Mystic and often gets overlooked entirely. It's a small, working village with a protected anchorage and a handful of moorings available through Palmer Cove. The lobster roll at Abbott's Lobster in the Rough is something sailors have been making pilgrimages to for decades — eat at a picnic table on the water and you'll understand why.

Further west, Essex on the Connecticut River is one of those places that feels almost impossibly charming. The river passage itself is a pleasure — wide, scenic, and well-marked — and the town of Essex has a proper maritime history that you can feel just walking down Main Street. Anchor off the town dock or pick up a mooring through the Essex Island Marina. The Griswold Inn has been feeding sailors since 1776, and that's not a typo.

Black Point and Niantic Bay are solid overnight options if you're making a longer passage or need to break the trip into manageable legs. Niantic Bay has good protection in most conditions and a friendly, low-key vibe that's a nice contrast to the more polished Connecticut River towns.

Rhode Island: Worth Every Extra Mile

If Connecticut is the warm-up, Rhode Island is the headliner. Narragansett Bay alone could keep a sailor busy for an entire season, and most cruisers from Montauk only scratch the surface.

Block Island is technically halfway there and almost everyone's first stop — but once you've cleared Great Salt Pond, keep going. The passage from Block Island to Point Judith takes maybe two to three hours in decent conditions, and it opens up the entire western shore of Narragansett Bay.

Wickford Harbor is the name that comes up most often when you ask experienced Montauk sailors where they like to drop the hook in Rhode Island. It's a well-protected, picturesque harbor with good holding, a friendly harbormaster, and a genuinely walkable town. The North Kingstown shoreline around Wickford has a laid-back energy that feels a world away from the Hamptons scene.

Dutch Harbor on Jamestown Island is another favorite, particularly for sailors who want solitude over amenities. The anchorage is spacious, the holding is good, and the views of the bay are the kind that make you forget whatever was bothering you when you left the dock.

For those willing to push all the way up into upper Narragansett Bay, Bristol, Rhode Island rewards the effort. The town has a deep maritime culture — it hosts the oldest Fourth of July parade in the country — and the harbor is well-equipped for visiting boats. Herreshoff Marine Museum is right there on the waterfront, and if you care at all about sailing history, you'll want at least a few hours to wander through it.

A Few Practical Notes Before You Go

Carry paper charts in addition to your chartplotter for this stretch. The waters between Montauk and Narragansett Bay have enough lobster pot buoys, ferry traffic, and local fishing boats that you'll want backup navigation if your electronics decide to act up.

VHF Channel 16 is always monitored in these waters, and the Coast Guard Sector Long Island Sound covers most of this area. File a float plan before you leave — even a quick text to someone ashore with your departure time, destination, and expected arrival goes a long way.

Fuel and provisioning are easy enough in most of the harbors mentioned above, but if you're planning a longer loop, topping off in Mystic or Wickford before heading further east makes sense. Pump-out stations are required by Connecticut and Rhode Island law, so plan accordingly.

The Sailors Who Know This Water Best

Ask around the docks at Montauk Lake or Star Island Marina and you'll find plenty of people who make this run regularly. The consistent theme in those conversations is that the Connecticut and Rhode Island coasts reward patience and curiosity. The sailors who get the most out of it aren't the ones rushing to tick off destinations — they're the ones who slow down in a harbor they've never heard of and end up staying an extra day because the crab chowder was too good to leave behind.

That's the spirit that makes Montauk a great home base for this kind of cruising. You've already learned to read this water. You already know how to handle a passage. The next horizon is closer than it looks.