On My Way: Cross-Island hike

The excitement from Long Point to Tashmoo Beach.


An electrical current coursed through the cool air.

I leaned against a tree and stretched my legs. Folks congregated outside the Trustees building. We had looked forward to the day. Even a conversation about the year’s ticks seemed to carry with it excitement. It was the morning of the 2023 annual cross-Island hike. We awaited instructions.

Soon Bill Veno, trail leader, quelled our nervous energy. We began the half-mile walk to the beach where last year’s walk ended and this year’s walk began. This was my second of the annual walks sponsored by the Martha’s Vineyard Land Bank. I discovered on last year’s walk not only an incredible traverse of the Island but also the camaraderie with the other hikers.

On the walk to the beach, I met a man named Bruce — a biker at heart, it sounded, and the owner of a craft brewery. We chatted for a ways, and discovered some connections. We were about 70 folks as we waited on Long Point Beach. The day was overcast, breezy, and chilly. I would add a layer. The ocean was turbulent and beautiful. Bill laid out the ground rules.

We went one by one over the sand dune. I began the hike with my boss, Allyson Malik, director of the Oak Bluffs library. The small pond to our right was wild and windswept, and gray with little seas. We made for the ancient ways that would carry us out of the wildlife refuge.

I had resolved to go slow on this hike. A month ago I pulled my Achilles tendon with ill-considered jumping jacks, and I had been nursing it back to health since with the goal of completing the annual walk. I brought my walking sticks for added balance.

The trail, once we had left the open meadow near the shore, was easygoing — wide and flat, and covered in pine needles. Still, I was cautious. I wanted to finish the full hike without injury. I soon was walking with local historian Tom Dresser and a friend of his, also Tom. After a good distance, we noted that the water — Homer Pond, I think — had accompanied us well inland.

I dropped back for a slower pace. The group was strung out on the trail. Bill left pink ribbons on branches to mark turns. I walked behind a family with two little ones in an off-road stroller.

After leaving one of the ancient ways for a dirt road, we passed a horse farm. The handsome creatures wore jackets in their pasture. In a few minutes, we crossed the Edgartown–West Tisbury Road onto the bike path. We shortly found a trail.

Brush reached out from either side. The center was hard-packed dirt, and sunken from the trodding of countless feet. The narrow trail wove up and down through the woods. The going with the stroller was difficult for the family in front of me.

The short trail put us back on the bike path. I could see the front of the group, about a quarter-mile ahead. We passed a statue of the heath hen, the now extinct Island bird.

Willow Tree Bottom, accessed off a fire lane, was the name of our next trail. The start of Willow Tree was open with short brush — oak saplings and other varieties — on either side. We walked in single file. The woods closed in around us. The brush matured to trees.

Our morning break was off the bike path, across the street from the West Tisbury School. Bill had stashed some refreshments there. I had a Kind bar and some apricots which I had brought. I had a water bladder in my pack.

This was not a leisurely break. We had to make it to the other side of the Island. Bill had us on our way again in short order.

We crossed Old County Road at the Whippoorwill Farm. We walked along the side of the tilled, planted fields, and turned onto Holmes Hole Path. Unexpected houses were tucked away in the woods. We recrossed Old County onto the Stoney Hill Path. I walked a while not thinking of anything. At its end, the path was a steep downhill, covered with stones. The path fed us onto Stoney Hill Road.

We were not long on the road. A connector trail took us to the Tisbury Meadow preserve. The group was well strung-out now. I walked on my own, without sight of anyone in front. I quickened my pace. I went through a number of four-way intersections with no pink ribbon, which indicated to me to go straight.

Finally, I caught the group ahead. Lunch was a few minutes in the offing. We arrived to the chosen location situated in a confluence of dirt roads near the Rogers Memorial Dog Park. Folks sat and stood, enjoying the break and some nourishment.

I chatted with some Sheriff’s Meadow folks after a tuna sandwich and an RX Bar and some water. I learned that the little wooden posts with the maps on top in the Sheriff’s Meadow properties are supposed to face North (to orient you in case you lose your direction).

I walked most of the afternoon with Tom Dresser. I told Tom we were in my neck of the woods as we walked a road in the Wapatequa preserve. We passed the Sailors’ Burying Grounds.

From the Mud Puddle Road we accessed a trail easement to the Bare Hill Land Bank property. In no time, we crossed the Edgartown–Vineyard Haven Road and accessed a trail that with some embarrassment, I admitted to Tom I did not know existed.

We went through the Winyah Circle neighborhood, and we walked down WinyahLane. We turned onto the Land Bank’s Ramble Trail Preserve. We hiked Ramble, and then the sometimes steep and canting trail of the abutting Sheriff’s Meadow Brightwood Park.

We really were in my neck of the woods. I walk Ramble and Brightwood Park all the time with Becham, my 26-pound terrier-mix pup. My home was a half-mile away. We came out of Ramble and the Brightwood Park at the Lagoon, near the Tisbury shellfish headquarters. A dirt lane delivered us to Weaver Road, and Weaver to Lagoon Pond Road.

We traipsed downward. We felt the wind strong on the pond as we passed the shack at the bottom of Skiff Avenue. The museum was up on the hill to our left. Tom shared with me a story of Vineyard history.

The little marshland in the Lagoon, he explained, used to be Ferry Island. Back in the 1800s. before much of the wetlands were filled, the ferryboat docked there. It took a while to wrap my head around that one, with all the pavement now obscuring the way. I tried to imagine the once-present waterway.

The afternoon break was in Veterans Field. My legs were tired and my feet sore. The first 11 miles or so of the morning had been easy. Now I was feeling the hike. We had some four miles to go.

The wind blew a gale as we stepped onto the beach next to the ferry terminal. One had to put one’s shoulder to the wind and push through in order to make way. Spring was nowhere to be seen. The wind carried a biting cold through my thin layers.

We walked the beach to the Vineyard Haven Yacht Club. From there we walked up to Main Street. Bill led us onto a dirt road that veered to the left. We entered the West Chop Woods.

Bill next turned us onto a fire lane. I trudged along the sandy path, ignoring the pain in my feet. The fire lane crossed Franklin Street, and kept on. We ducked under or squeezed through a number of metal-tube gates. We crossed Daggett Avenue onto Herring Creek Road.

We were almost there. Tom and I walked the final stretch. We chatted about the finish, among other topics. Herring Creek is a narrow and long dirt road that weaves within the banks of trees.

The tidal mud flats of Tashmoo appeared to the left. The beachfront houses were on the right. The sandy dirt road rolled ahead with a series of large bumps that put the chassis of cars to the test.

We came to the finish. We joined the folks massed together. The day was as gray as it had begun. The wild waters ran through the Tashmoo Channel, and the wind swept over the beach. There was no way further to go. The exhilaration was among us.

I looked forward to the comfort of the warm car. Peter, my son, was there to pick me up. The day was not quite done, though. I waited in line to write my name in the book.