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Cruising to Watch Hill, RI

Watch Hill, RI is a laid-back, small upscale beach and boating community that should be on your port of call list when cruising the region. Located on the southwest tip of the state, it is surrounded by water on three sides. This includes the Atlantic Ocean / Block Island Sound, Pawcatuck River, and Little Narragansett Bay.
As opposed to the more popular and bustling Newport to the east, Watch Hill has been said by the New York Times as a “community with a strong sense of privacy and of discreetly used wealth” While Newport has the over-the-top castle-like mansions, Watch Hill’s has their multi-generational sprawling restored Victorian homes. Watch Hill likes its comfort and luxury in a lower key setting than Newport. It is also a much smaller and quieter place.

Cruising and Overnighting in Watch Hill
Cruising to Watch Hill from the Long Island Sound has you stay north of Fishers Island aiming for Stonington, CT. Coming from Long Island’s south shore or Block Island you need to enter the waters between Fishers Island and Napatree Point. Under no circumstances are you to get to Watch Hill by turning starboard past Napatree. All boaters need to go north to Stonington and slow down at the no wake signs. From there, follow the channel markers with no deviation around Sandy Point Island south until you reach Watch Hill Cove.
If you have the time before or after your stay in Watch Hill, cruise east of the Watch Hill Lighthouse. Here you will catch the view of the iconic Ocean House to the right, Taylor Swift’s mansion in the middle, and the lighthouse on the left.
Watch Hill has three ways to sleep aboard. One option is to try to reserve one of the several slips through Dockwa for the Watch Hill Docks. The docks are in the middle of the cove on Bay Street. These are non-floating docks with a 3-foot tide difference. Dock Master John did a great job tying us up. I recommend you reserve well in advance as they are popular. The price in 2022 was $6 per foot plus power.
Option two is to get a mooring ball through the Watch Hill Yacht Club. Doing this can be challenging. Watch Hill is first come, first serve on the moorings. The problem that arises here is that they take reservations for clubs coming in meaning the mooring balls can be taken. You cannot find out about this in advance because they are not good about returning calls in regards to their mooring balls. They have a launch service that takes you to the yacht club.
Option three in Watch Hill is to throw the hook in the shallow calm waters around the corner from the cove behind Napatree Point.
There is a good grab and always a breeze here. Boaters can use the free dinghy dock off Bay Street.
We combined our stay with two nights on the dock and one night on a mooring ball outside the cove. We recommend outside the cove because it is a good place to swim off the stern.

Bay Street
Going to the beach in Watch Hill

There are a few places to enjoy the water.
Napatree Point juts out over a mile into the Block Island Sound (most people called it the Atlantic Ocean or just the ocean). This is conservation park is open to the public either on the ocean or bay side and only walk on the designated paths.
To use the beach on Napatree you can pay $12 per adult to enter near the carousel. There you have some services including being able to rent chairs and an umbrella. If you brought your chairs I would pass paying the fee. Instead, walk to the end of Fort Road to the free conservation area entrance. From here you will walk about three minutes to the oceanside beach. The ocean side is much nicer than the bayside beach.
For quieter waters to float in we liked the top of Watch Hill Cove on the west side. To get there walk to the end of Fort Street and stay right after the free entrance. You may see small speedboats anchor by the sand with families enjoying themselves. For children, bring a net to capture and learn about little sea creatures that live in this area.
Our favorite beach was located near the beautiful Ocean House Resort. You can access the beach past the road to the lighthouse on Bluff Ave or go another block past the Ocean House. If you walk down the beach off Bluff Ave your piece of sand will be between the Ocean House and Taylor Swift’s imposing 11,000-square-foot mansion above. If you enter past the Ocean House you will have fewer people around you.
Another option beach option is to take your boat back up the channel towards Stonington. Find a place to anchor off the east side of Sandy Point and swim or dinghy to this 2000 by 200-foot narrow island. The island is designated a bird sanctuary and the narrow interior is roped off. There are also no dogs allowed here to protect the eggs or baby birds.
Things To See
The Watch Hill Lighthouse makes a nice stroll during the day or after dinner. It is a five-minute walk up the hill from Bay Street to Light House Road. It is another five minutes on Light House Road where you will pass several pretty and restored mansions until you reach the end.
The Watch Hill Lighthouse has its history going back to 1745 when it was a tower and beacon. The present structure was built in 1856. Here you have views of the Ocean House and Taylor Swift’s mansion to your left, Block and Long Island ahead, and Fisher’s Island and Connecticut to the right.
The Watch Hill Conservancy offers free Saturday 9 AM nature walks on Napatree. A conservationist meets people at the end of Fort Road where the entrance to the park is. From here it is an easy 60 to 90-minute stroll stopping in different places to learn about the birds, flora, and things from the sea.

Bay Street
The 600 feet of Bay Street is for retail therapy. Here you will find several fashionable boutiques, a pottery store, souvenir shops, a jewelry store, and a skincare shop. For the sweet tooth, there is a candy shop. Unfortunately for boaters, the nearest place for provisions is Stop and Shop about five miles away.
A popular time to be on Bay Street is at sunset. Here you will find dozens of people sitting on the sea wall or grass enjoying the last moments of what was a fun day.
The Flying Horse Carousel built in 1876, and located at the end of Bay Street, is the only carousel of its type operating in the country. To ride it, children here are strapped onto a hand-carved wooden horse. Swinging poles attach the horses from the top giving the feeling of slowly flying around. Outer riders get a chance to pull the lucky brass ring. Note the real tails and manes on this movable piece of art.

Watch Hill in my opinion can use a few fewer boutiques and perhaps another restaurant or pub as dining is limited here if you stay more than a few days.
Ocean House Bistro was our splurge for a fine dining lunch before enjoying the beach on this side of Watch Hill. My New England clam chowder was not too thick and had the perfect amount of clams and bacon flavor. On a recommendation, I also went for the lobster roll. This was served with large pieces of just steamed and picked apart lobster with hot butter on the side. After lunch walk around this stunning old-world hotel-style resort. Admire its art, details on its interior, and views of Long Island and Block Island.
There are five good restaurants at Ocean House if you come back for dinner. They also have a lobster seafood night and gourmet wine tasting dinners. Reservations are needed in season. If you are tired of sleeping aboard and want a treat, check-in for the night where you will get beach privileges.
The Olympia Tea Room has been serving dinner for over 100 years. There are many good drinks to pick from their craft cocktail menu to start. The food here is continental with a push on seafood. We enjoyed the steam clams’ starter, baked haddock, and their pasta dishes. Leave room for their tart and tasty Key Lime Pie. They don’t take reservations.
The Watch Hill Yacht Club is an imposing three-story building in the cove. The dining room here has a commanding view of the boats and sunset. We found the food good and service very friendly on two visits.
Dining here is a little complicated. They don’t take reservations from non-members except for the same day. They also require jackets in the main dining room. (Some men wore jackets with shorts.) However there is a corner in the dining room with a few tables where jackets are not required and it is first come, first serve here.
It was not made clear if you need to be a member of a reciprocal club to dine or if just renting a mooring ball from them that gets you in. We entered the dining room, signed the book, and sat down at one of the casual tables. No one asked to see our membership card from our yacht club though we did moor there one night. The casual section has both a regular and pub menu.
The Bay Street Deli is a good spot for a quick sandwich. Try their Rhode Island clam chowder. Rhode Island chowder uses a seafood broth as opposed to cream based for New England style or tomato-based for Manhattan clam chowder
Ten Sandwiches is just as the name states. They make ten sandwiches along with salads and in the evening flatbreads. They have a cozy bar with a good selection of Tequila.
The St. Clair Annex has been around for over 125 years. This is the place in Watch Hill to try one of the many house-made flavors of ice cream.
For Long Island Boating World’s story on cruising to nearby Newport, RI click
U.S. Coast Guard Licensed Captain (and Master to 50 tons) Tab Hauser writes and photographs about travel and boating worldwide. He currently runs www.GlenCoveCruises.Com and charters out of Glen Cove. You can find some of his cruising stories by web searching “Tab Hauser Boating” or email questions on cruising to