your paddlesports destination

Shelter Island in New York

by B

Trip Overview


9:15 a.m. An hour after low tide, I launch my Old Town Otter from Crescent Beach. Striped bass break the surface just north of the beach near the bluff. The days first jellyfish begin to arrive in droves. The bay is flat as glass. Very few boats. A man and child mill around outside a house at the base of Whites Hill.

9:20 a.m. Right away I feel my right bicep and shoulder twinge then ache, telling me I shouldnt be doing this, but I go on anyway. The discomfort soon dissipates as I round the corner toward North Ferry. Must have been my body waking up telling me its too early for physical activity.

9:30 a.m. I approach North Ferry slips and wait for two boats to leave and another to dock so I can make my way through. Four boats running. I paddle through as another boat is halfway across coming from Greenport. I do a sache of sorts through the rudder wash of the Islander and continue headed for Brownlies.

9:40 a.m. I can see Hay Beach Point, but it looks very far away, like Ill never get there. I snap a picture of Dering Harbor, the Yacht Club and the many boats that litter the harbor creating a setting for an East End seascape painting, with my throw-away camera. I can hardly put my paddle in the water without hitting a jellyfish. Some are breaking the surface just bobbing along, others are floating a foot or two below, sideways, letting the soft current take them to their destination. These are some of the largest jellyfish Ive seen in years. Sizes ranging from softball size to basketball size with tentacles stretching the length of my paddle in some cases.

9:45 a.m. I pass Brownlies and Walkers and pass up good photo ops at each, hoping to save pictures for later in the day. Hay Beach Point is still way off in the distance. I know through my course plot that it should take about six hours to go the estimated 16.5 miles around the island. So to feel the slightest discouragement less than an hour into the trip is disheartening.

10:18 a.m. Finally! I make it around Hay Beach Point and see something other than the same horizon I had looked at for over an hour. Checkpoint one reached. I pick up the pace knowing Ive gotten over one of six hurdles.

10:30 a.m. I cant believe how many cormorants are on the rocks and in the water. Theyre bathing, drying wings, diving for fish. One swims about 20 feet away as if escorting me for a few minutes. I snap a picture of Bug Light, which is almost behind me and to my left by now.

10:40 a.m. I pass through the rocks and glide by Menhaden Lane and the first causeway to Little Ram, peering at my next checkpoint in the distance, the north face of Big Ram. That seems far off, but not as bad as Hay Beach Point did.

11:01 a.m. My battery-operated radio, which also transmits weather bulletins, alternates between 99.1 FM WPLR and 98.5 The Bone, both classic rock stations, and they indicate its 11:01 a.m. I decide to move a little faster since Im expected at Big Ram by 11:15 or 11:20.

11:20 a.m. I make it to Big Ram still going against the tide a bit until I round the bend toward Reel Point. I watch a woman on the beach pack up her things from a morning relaxation and head up the long flight of stairs all the way up a bluff to her house overlooking Gardiners Bay. I am also curious about the big black dog that I think is looking at me from the beach. It is actually a wooden cut-out made to look like a dog lying down. Neat. Next target Cedar Point across from the outside of Mashomack.

11:30 a.m. I breeze past Reel Point and start to feel the current take me toward Mashomack. I am making up time, not that Im trying to break any records. A few boats entering and exiting Coecles Harbor slowly pass by the buoy, one captain waves in acknowledgement.

11:50 a.m. I pass through cormorant-laden rocks off the outside of Mashomack and snap a picture as they fly off. Im able to get close because they cant hear the kayak. Im about 500 yards off shore paddling the length of a long beach toward Mashomack Point.

12:15 p.m. Halfway! I snap a shot of Cedar Point lighthouse and continue paddling. I begin to eat my roast beef and swiss on potato bread. I worry about the mayo that has been heated up by the sun. A few minutes later I reach Mashomack Point and round the bend. After three hours of extremely calm water, I notice a shift in roughness and current. Two people dig for clams near the points creek entrance.

12:25 p.m. I call out to an osprey I see on a nest pole and he flies off. I turn off the radio to enjoy the serenity and beauty Mashomack has to offer. Nothing beats the salty-marsh smell of the nature preserve. I cant even see South Ferry at this point in time. Mashomack is longer than I expected and I worry that Ive misjudged my timing of arrival at the green buoy near South Ferry Channel. 12:55 p.m. Passing Majors Harbor and heading right through the middle of the bay I spot a crane working on a dock in North Haven and finally see South Ferry. Ill be coming through the South Ferry channel in about 15 or 20 minutes.

1:10 p.m. I wait at the green buoy for a minute while a sailboat leaves the channel, and then around to face the wake created by a 30-foot speed boat approaching the channel. Turning around again I watch as three ferries shuttle passengers back and forth and a captain takes another empty ferry for a spin toward North Haven and the Garr Estate. I wait as one ferry leaves for North Haven, one sits in the S.I. slip and another is still in the N.H. slip. I decide to make my move. I am thrown about like a pair of socks in a washing machine as the current whips me through. I cant even think about taking a picture of the ferry until it gets calm again.

1:30 p.m. Ive drank half of my three quarts of water as I pass the old Garr Estate. I take a picture of the old stone pier with manor house in the background. I take another picture of Wades Beach. I paddle for Shell Beach with a little chop in the water. I pick off the broken down bulkheads off the south side of Shell Beach one by one. As I round the outer section near Peconic Avenue I photograph an osprey nesting on top of a red-roofed gazebo at the end of a dock. He stays and does not fly off.

2:00 p.m. Rounding the outer edge of Silver Beach it seems like forever until Ill get to Crab Creek. Its choppy, my arms are starting to sizzle and Im drinking more and more water.

2:10 p.m. I pass the entrance to Crab Creek where three boys are sitting by the entrance and head around the point toward Bootleggers Alley. My arms are burning now. Only an hour left.

2:20 p.m. Just as high tide approaches, I take a picture of the Greenlawns and continue past a few docks lining the beach. Many more fishing boats on the west side of the island. I can see Port of Egypt in Southold by now.

2:50 p.m. I see Kissing Rock, take a picture looking up the road from the rock and begin to feel a sense of accomplishment. I know when I round Jennings Point and pass the gazebo its going to feel so good. Just for good measure I approach the gazebo and take a picture right before Im nearly swamped by the wake from a cigarette boat.

2:55 p.n. I can now see the Pridwin, Perlmans and Crescent Beach. What a sight! I can coast home now. Enjoying the last few ounces of water I finish and cup my hand with sea water and let it drip over my head, neck and back. I pass some sunfish sailboats during their sailing class at Camp Quinipet, one crew waves hello. Now that I know Im almost done my arms feel even more tired, but not so much that I cant finish. I notice beach umbrellas with colored panels and familiar vehicles lining the beach parking.

3:10 p.m. I watch as my wife gets up from her beach chair, greets me feet from shore and welcomes me back. I hand over the camera, raise my paddle expressing delight in the accomplishment and she snaps a picture. Five hours and 55 minutes later, my trip is complete.


Sandy beaches, many town landings for put-in spots. Minimal public restrooms.


Beach parking permit required. Can be purchased per day or for season. Beach driving permit required. Permits available at Town Hall.


From LI Expressway: LIE Exit 73 to Route 25 to Greenport. Sign says SI FY for Shelter Island Ferry. Make a right on Front Street to North Ferry dock.

From Sunrise Hwy: Route 27 (Sunrise Hwy.) east to Noyack Rd. Follow to Long Beach Road through traffic light to Rt. 114 North. Follow to South Ferry dock.

  • Skill Level: Advanced
  • Water Type: Open Water/Ocean
  • Group Rates: No

Locations on this Trip