On My Way: Kayaking the Chop and beyond

Paddling to the beating heart of Oak Bluffs Harbor.


I have long been enamored of the small, circular Oak Bluffs Harbor that summer folks flock to in droves. The numerous million-dollar yachts tied up to the slips along the concrete wharf are always fun to see. Inside the harbor, nearly every mooring bulges with boats rafted three to four deep. It is the latter that has captured my imagination.

I pushed off Hines Point town beach in Lagoon Pond in the late morning. After a few words with an Island fisherman taking respite in the water, I sat in my kayak and set for the bridge. The beginning strokes of the first few paddles are always wonderful.

Before I had gone more than 20 or 30 yards, I saw a man wearing a wide-brim hat coming at me from the other direction on his paddleboard. This man, it turned out, was my brother Douglas. 

Without a thought, he turned around and joined me. Douglas is always game. We chatted, caught up, and paddled at a relaxing pace. He told me he recently discovered a new bicycle route. Passing through the shellfish buoys off Hines Point, we crossed the pond and floated under the bridge in a light tide.

This is where Douglas bailed. He already had been up and down the pond, and he had not signed up for a trip around East Chop on his paddleboard. He made his turn, wishing me fair winds.

I pulled for the end of the Eastville jetty. My mind was immersed in the summer day. I rounded the jetty and pointed for the open waters. My paddle was well underway.

I looked into the breadth of outer Vineyard Haven Harbor. A catamaran sailed under its mainsail on the western side, and a trimaran sailed under a poled-out spinnaker. A Jet Ski came flying down the middle. 

I passed by the few boats anchored off Eastville Beach. I was making good headway. I stayed 100-plus yards off the East Chop shore. I noticed the summer homes built along the beach had survived another winter.

It was a lovely day for a paddle. I did not feel a tide, and there was no wind to speak of. Seas were a calm one to two feet. Some areas undulated with glassy swells. I focused on my strokes. Soon I was rounding the bluff.

The waters off East Chop lived up to their name. Steep two-foot seas were headed in every direction. The wake of passing motorboats added to the fray. I knew these little waves could swamp my boat if I was not careful. 

The kayak jolted and tipped. I kept my center of gravity above the water. It was a fun paddle. I felt the jolting turns and straightaways of a rollercoaster. I pulled hard on the paddles. The kayak shot through the confused sea.

The area of chop did not last. I passed the umbrellas and beachgoers of East Chop Beach. I approached the turmoil of the Oak Bluffs Harbor channel. I was given a “yee-ha” by some folks as I powered through a rolling wake.

I took a look and saw an opportunity. The channel was relatively empty. None of the numerous ferries were making way. Only a few small motorboats plied the narrow waterway. I took my chance and jumped in. The short passage was uneventful.

Once in the harbor, greeted by a large, oceangoing catamaran, I paddled around the inside of the East Chop Beach. I had not known the small sandy shore existed. A Jet Ski was parked at the water’s edge, and folks were sunbathing.

I went along as far as I could. I turned though the docks of the East Chop Beach Club. I then directed my kayak into the center of the harbor. Here I found the beating heart.

Big oceangoing yachts rafted up. I watched a 40-foot yacht pull up alongside another of similar size in a barely navigable passage. It seemed impossible to me that the mooring field could handle the density.

Unlike its maritime cousin of Vineyard Haven, where every other boat seems to be a schooner, the sailing vessels of Oak Bluffs Harbor were few and far between.

I talked to folks from Connecticut who were staying a few days, and folks from Bourne who were there for the afternoon, and maybe grabbing some sushi. Numerous parties enjoyed swimming in the water off their sterns.

One group consisted of 15 to 20 people. Many were sitting in the water chatting and enjoying drinks in hand. The rest were congregated on the stern decks. Drinks poured freely. The rafted boats had become one.

I said hello to a family from Mattapoisett. The attention of two kids was devoted to unrolling a floating dock. With an assist from the father, they succeeded. I asked if I could take a picture. They were more than happy with the idea.

“What do you want us to do?” they asked. 

“Jump off,” I responded.

I continued through the mooring field, and came out on the slips of the concrete wharf on the inside of the harbor. I paddled around along the outside of the mooring field back toward the channel. 

More moorings were with rafted-up boats. The inside orb of the harbor was now again hidden from view. I was not let down with my exploration. 

The channel was busier this time. Multiple large motorboats were outbound, and the inbound fast ferry was blowing its horn in warning. I hugged the jetty to avoid the maelstrom, and blew out of there as fast as possible.

Beyond the entrance, I crossed back over in the direction of East Chop. A breaking wake of a large motor vessel careened at me. I put my bow directly into it. I was unable to go up and over without taking on water. The wave washed over me.

Back off East Chop, the waters were again exciting. There was a light breeze now, giving the chop added force and momentum. I felt the thrill of being on a rollercoaster, and pulled through. The kayak found its way amid the jolts and knocks, and I felt my vessel’s commanding speed.

The East Chop Light, a beacon of safety and hope for sailing ships, stood on the bluff. Out in the sound, a number of sailing yachts with carbon-gray sails headed East. I wondered if a race was happening.

The water was shallow off the bluff. I could see bottom. I paddled out to a green buoy to see if the current was running. There was not much. I made for home.

The wind was out of the south. I felt little opposition to my strokes. I focused on continuous paddles without stops and drifts. A regatta of small boats sailed on the side of West Chop.

I came back through the sailboats anchored off Eastville. I rounded the jetty, passed by the folks on the beach, and drifted under the bridge. Two young fishermen had their lines out.

I crossed the pond back to Hines Point. I had some strength left in my tired arms. I came by the crescent beach, now covered by the tide. I heard a beautiful chirping. I looked up and saw an osprey nest on the top of an almost-derelict motor vessel. The parent gave me a hard look as the heads of the chicks peeked out. It was a good ending. The music of nature stayed with me as I skidded up onto the beach.