Leaves along Connecticut’s Route 9 had begun to trade their deep green for hints of orange and yellow; nature was showing its hand. Fall is here. With a long holiday weekend on tap the Karen Marie would be chasing the horizon at full throttle trying mightily to catch back up to summer.
That’s how it came to be that we motored from Essex early Saturday morning, hitching a ride down the river with an outgoing tide. The early, yet strong rays of sun burned off the morning dew providing a smoky hue to our cruise. Short chop in the Sound and the confused waters of Plum Gut made for a less-than-leisurely ride over to our destination of Shelter Island’s Dering Harbor. Covered in a weird combo of salt spray and sweat, we eventually tied up to our mooring in the southeast corner of the harbor and took in the view of sailboats and blue-hulled powerboats bobbing up and down in the clear water surrounded by beautiful homes and lush green tress.
After a bit of settling in, we hopped in the dinghy to explore town. It would be a short trip. The main street in town, and the hub of activity, is a short block comprised of a True Value, a gas station, toy store, a rustic looking bar/restaurant called Dory and a café/deli/grocery store called Marie Eiffel Market where we stood on a line nearly out the door for a pair of excellent sandwiches. It was clear that we would be back.
After a bit of R&R I had a little “work” for the magazine to tend to. For the next issue’s gear column I was testing and photographing a uniquely shaped inflatable standup paddle board called the Sea Eagle NeedleNose 126. (I know, I know…tough job!) The paddle board ended up working great; it went from rolled up in a backpack to fully inflated in two minutes and as you can see from these outtakes, it ended up being a lot of fun.
An evening of grilling and watching the sun set capped off the rest of a pleasant night.
Day two was kicked off the Shelter Island way with breakfast from, where else but Marie Eiffels. Determined to better see what the island had to offer we rented bikes from the gas station (apparently specialty stores aren’t real popular here). The plan for our half day rental was to take a “nice easy” ride out to the northeast jetty and then double back to a marina/boat builder called CH Marine where we could shower and inspect any new builds in progress. Well, that plan lasted until the first stop sign when Karen tried to pass me. A two hour race would ensue that I’m sure did little to help tourist relations. (When the island wasn’t whizzing past, it was really a beautiful way to see Shelter.)
Stopping at CH Marine yielded both refreshing showers and the chance to see a newly built 34-foot runabout. With a really unique blue Awlgrip paint job and sweet down east lines, I was not alone in ogling the new build. Many visitors stopped to snap a few pictures.
Refreshed and feeling like humans again, we hopped a 5-minute ferry ride from Shelter to Greenport, a beautiful town that is often referred to as one of the most beautiful on Long Island. The thing about the most beautiful place on Long Island on the most popular weekend of the summer is, well, it gets pretty darn crowded. Crowds of inebriated college kids, ice cream-covered children and older couples filled the streets in what would be become a very strange scene. We would enjoy a cold beer at the Greenport Brewery before I convinced Karen that it would be in our best interest to explore a nearby down-on-its-luck boatyard. She hardly puts up a fight anymore and just rolled her eyes. After climbing around a few rotten wooden boats, I found a real gem. Something that 7-year-old-boatyard-exploring-Daniel could only have dreamed of…tucked being an abandoned rust covered building, surrounded by a small flotilla of derelict sailboats was…a 1967 Lockheed submarine. My jaw dropped as I took in the site. “You can trespass in boatyards your whole life and never find something like this,” I whispered to Karen who began to realize another plan, this time for a “5 minute yard visit” was going out the window.
After poking around the sub for too long, we decided to end the day with a drink at the waterfront bar called The Blue Canoe. Watching the sun set with a couple cold rum drinks, you couldn’t really write a better official end to the summer.
We’d return home the next morning and our mini vacation, much like our bike ride, and our summer, would end all too soon. But this short weekend reminded us of how much we enjoy cruising to, and exploring new destinations. There’s just a certain excitement that comes with not knowing what’s around the next corner, it might just be the submarine you’ve spent 20 years searching for.
Boy and a Boat 
Reblogged this on Jason Y. Wood and commented:
That’s how it’s done.
Awesome story. I can relate to your every story. You took me back to my childhood. Thanks for sharing as I am sitting in the cockpit 1 week later wondering where summer and the crowds went. Thanks for sharing.
Great pics and a good write up. Looking forward to more adventures from you.
Tiffany, sailingchiron.com
Thanks for sharing your tales of Greenport and Shelter Island, two of my favorite places on earth. I spent more of my mis-spent youth than I care to admit in the Dory, and my first marine industry job was in a yacht brokerage in the Greenport Yacht and Ship boatyard. You took me back to all of that, and in a good way. Thanks Dan!