Cruising to Cuttyhunk Island

Our alarm clock blared at the all too early hour of 5:00. Groggy, yet excited for our 26-mile leg to Cuttyhunk, I sat up and peered out our portlight to watch the first rays of sun crest the horizon. What I saw surprised me … nothing. A blanket of fog smothered Jamestown Harbor. It wasn’t until 7:00 that the sunlight permeated the low-lying cloud cover and we set out. A piping-hot cup of coffee was a welcome start to our delayed trip. Rolling 4-foot swells in the inlet, not so much. We were headed west, in the direction of the wind, requiring us to run the engine the entire trip.

The relentless barrage of seas on our starboard side made for a rolly trip. After four hours of bracing ourselves in the cockpit, the southern end of the southernmost Elizabethan Island appeared off our bow; we were finally approaching Cuttyhunk. The hilly Ireland-like landscape is a feast for your eyes, but the narrow approach to Cuttyhunk Harbor demanded concentration. A few silent Hail Marys later and we were tied to a mooring. I opted to celebrate our successful trip by diving into the cool-clear water, which the island is known for. The stress and apprehension of the day washed off before I could surface.

I had been to Cuttyhunk before, but as a young lad, and the clear water was something I remembered well. The other thing I remembered was a World War II bunker on the highest point of the island that served as a U-boat lookout. Filled with equal parts energy and imagination, my brother and I climbed through it for what seemed like hours. It was disappointing to see that the fort has since been boarded up; the view of Martha’s Vineyard from it however was incredible, especially through adult eyes.

This walk was followed by a lazy afternoon of swimming, sipping cold beer and checkers. A dinner of ribs aboard my parent’s boat was a delicious way to end the day. We cleared our plates and were content to sit in silence and watch the sun set behind the hills of Cuttyhunk. First a shade of yellow, it morphed into a brilliant orange before turning into a deep red that illuminated the sky and mirror-calm water around us.

Waking up with sun pouring through our overhead hatch and fresh air wafting through the boat refreshed and energized Karen and I and we immediately set out to explore Cuttyhunk. A small bakery, just feet from the dinghy dock attracted mooring dwellers like mice to cheese. Breakfast of pastries and coffee was a simple, yet satisfying start of the day.

The first stop on our island hike was a small non-denominational church with nautical décor that hasn’t changed much in its 100-plus years of service. A one room schoolhouse and library were both closed, but peeking through the windows, you couldn’t help but marvel at the quaint way of life here.

A well-worn trail took us from the highest point of the island, and the bunker I remembered from my childhood, to additional World War II era observation bunkers that were still open for kids, like myself, to climb into. Dreams of being a U-Boat spotter flooded my consciousness. We tried to get to the southern-most point of the island but a flooded trail stood in our way. Maybe next year.

An afternoon dinghy ride took us past a 3-mile long stretch of land owned by the Forbes family called Nashawena Island. We were shocked to see a wild herd of Scottish Highland Cattle strolling the beach. Set against a backdrop of rolling green hills, it’s easy to believe we were somehow transported to northern Europe. And that was before a curious seal poked its head out of the water just a couple hundred feet from our raft.

Our attention-starved puppy entertained us, when we stopped at the beach, with her impressive swimming abilities and seemingly endless energy. A respectable runner myself, Zoe seemed to be smiling as she smoked me in a series of beach races. Another alfresco dinner and drop-dead gorgeous sunset wrapped up our short time on the island.

Cuttyhunk Island has a way of forcing a simple lifestyle on you. It’s a place that makes you face life’s tough questions like: “Do I go swimming then hike, or hike then go swimming?” Like a pair of boys running around an empty bunker, my two days here reminded me that sometimes it’s the simplest things that leave you with the sweetest memories.