We love the laid back peacefulness that is Cuttyhunk. Sitting pretty at the SE end of the Elizabeth Islands chain, with Buzzards Bay to the north and Vineyard Sound to the south, Cuttyhunk oozes island time even during the high season of July and August. We last visited on our “bring her home trip” June 2010 and not much has changed. Each time we come we learn more and find a different path to wander down.

Our usual island stroll always included a walk up the paved street to Lookout Hill. This time armed with the camera and the knowledge bestowed by the island map we set off from atop the Hill on a path to the WWII bunkers.  Or maybe it was the other one; both were narrow, unmarked and only the tramped tall grass labeled it as a path. Taking the road less traveled was going to make a difference; we ended up in private property looking out over the Gosnold Monument erected to honor Bartholomew Gosnold, English discoverer of Cuttyhunk.

Key West has Southernmost, The Elizabeth Islands have Gosnold Monument. Cuttyhunk Shellfish Farms has new oyster beds set up here; you can see the floats in the water if you squint.

Despite our poor map memory skills and sense of direction we managed to circle back to the obviously correct path to the bunkers.

Cuttyhunk boasts apprx 50 year-round residents. Its island seams burst to 400 during summer, including boaters.

Bass fishing in the surrounding waters was extremely popular; the mascot of the Corner Store is the Black Bass- you know, like the Black Dog. Fishing may be great but we drool over the fresh oysters delivered fresh to your boat most every evening by the Raw Bar. Wednesday evening, with a respectable flotilla of boats in the harbor for off-season, we blew off a beach visit (way too windy) in order not to miss the Raw Bar. We may have been last, but no way least. Our order of 6 oysters on the 1/2 shell was delivered up not only with souvenir trinkets but with 6 free littlenecks on the 1/2 shell. The boat had prepared but not sold them and as you know good things come to those who wait.

In addition to the 50-ish moorings in the harbor, and the 30 outside the harbor, Cuttyhunk grows a variety of mooring we’ve never elsewhere encountered. In fact, until this visit we didn’t know what they were. Pilings standing in the water. In rows. Yep, clueless crew. This time, not only did their true nature come to light in an ActiveCaptain review, but boats were using them- providing a show and tell to our dimly lit brains.

These offer more swing room than the main bobbing ball field which is pretty tight. Friday morning when I got up the giraffe neck pennant part of the mooring was wedged under the dinghy.

Titanic imitator or just trying to grab the mooring…. you decide.