On My Way: Cross-Island Hike

From Big Bridge to Long Point, and points between.


The 2022 Cross-Island Hike, sponsored by the Martha’s Vineyard Land Bank, was as much a celebration as a 19-mile trek.

For the uninitiated, including myself until a week and a half ago, the hike is held annually on National Trails Day, the first Saturday of June. I found out from a patron in the Oak Bluffs Public Library.

The day began 8:30 am at Big Bridge. I had a pack with lunch and a bladder of water. The drinking hose came out of my pack right near my mouth. I also had a water bottle with a replenishing Nunn tablet. I had Band-Aids and moleskin.

My mother dropped me at the start. Coming over the bridge from the Edgartown side, a group of about 40 hikers appeared. My heart beat a little faster. My mother pulled the car over. I walked across the street to join the group.

The day was much cooler than forecast. A light mist shrouded the hikers. I had on shorts, a long-sleeved shirt and a wide-brim hat.

The group looked mostly older than my 52 years. I saw a few I recognized, and mostly those I did not. Folks congregated and waited to begin. Expectation of a good hike hung in the air with the mist. The group looked experienced. Hikers had packs with water bladders, and wore good footwear and hiking pants. Nearly everyone had a hat, and a few had walking poles. Everyone looked game.

I stood in the back. A gregarious older woman — in her mid-to-later 70s I would guess — was beside me. We said hello and talked a few minutes. She spoke with a big smile.

Near the set start time, Bill Veno, the trail leader, gave a short introduction which I was too far back to hear. Exuberance was palpable.

We went shoulder to shoulder over the bridge in the direction of Edgartown. I met a friendly woman who had moved to the Island from Arlington, and a young man who had recently moved with his young family from Hawaii.

We came to the Caroline Tuttle Preserve. We turned in and did a short U-shape loop. I struck up a conversation with the wife of my son’s high school cross-country coach and her daughter. Caroline Tuttle is an interesting trail with some ascents. We came back out on the bike path headed for the Edgartown Triangle. 

I caught up with the front walker. We arrived at Cannonball Park. We stopped at the Land Bank building across the street for a bathroom break. From the Land Bank, we made our way to the Edgartown cemetery. A town easement then allowed us over private property. The group walked as one. 

We filled the trail in a column, with folks abreast of each other. I walked this section with my boss Allyson Malik, director of the Oak Bluffs library. Forest was to either side.

Bill pulled us over into a small clearing for a mid-morning break.

A garbage bag full of bananas, peanut butter crackers, apples, and gallon bottles of water had been left. I took a package of the crackers and drank from my water. Folks were in high spirits.

After our allotted 15 minutes, we were back on our way. Bill turned us before we reached Morning Glory Farm. We continued on back ways and came out onto the Edgartown–West Tisbury Road, which we crossed. 

We hiked along the side of the Vineyard Golf Course and traversed through the Pennywise Path property. We walked a fire lane and connected with Dr. Fisher Road. Dr. Fisher, along with a few other trails, brought us near the MVRHS baseball field. We continued on the paved road to the Edgartown–Vineyard Haven Road. 

We arrived at the YMCA at 12:30ish. We had made 12 miles or so in about four hours. We sat at the outside picnic tables for a well-deserved noon break.

Hungrily, I ate my thick tuna sandwich. Folks had sandwiches and Oreo cookies. I drank from my water bottle with the Nunn tablet, and chatted with the wife of one of my library colleagues. I ate a salty dark chocolate Kind Bar.

Bill gave us half an hour.

We started the afternoon on a trail behind the Y, passing the Woodside development. We crossed Barnes Road, and not long later crossed the Ed-V.H. Road. We turned into the woods.

Never was there a lack of trail to carry us along.

We passed the Vineyard Youth Tennis bubble. We waited at Barnes Road for an opening in the traffic, and crossed en masse. A trail along the other side of the road delivered us to the State Forest buildings. We were on land that I knew.I have walked with my terrier mix pup Becham many times in this section of the State Forest. Bill led us onto one of the familiar trails. A jolt of energy coursed through me. We came to a great big meadow. 

I talked with a woman whom I recognized. Soon we realized that we have often run into each other walking our dogs at the Tisbury Meadow property. We laughed.

We re-entered the woods on a trail headed south. Not too long later, and after a brief turn west, we arrived at the location of our afternoon break. We were beside the bike path along the Ed-W.T. road. Bill found the water and snacks.

We had gone over 14 miles. 

The group was a little more spread out. Clusters of folks trickled in one after another. Some sat, others elected to stand, not wanting to have to stand back up. I drank some water and ate an RX bar.

The woman with whom I had chatted before the start appeared. She had the same big smile. Needless to say, I was impressed. 

My feet were a little sore. My legs and back were beginning to ache. The first 14 miles had been terrific. The last five were going to be a little more grueling. 

Bill started us up again. We crossed the Ed-W.T. Road, and trooped along on a dirt road. I chatted with some new folks. Spirits remained high.

I walked with Bill a ways. Bill is trails manager for the Land Bank, and also is a planner with the Martha’s Vineyard Commission. He has led the walk for some 20 years. He was happy to share some of his knowledge on the ins and outs of public ways.

Bill is a tall man with an easy gait. He appears on a casual stroll. You would not realize he is doing over 3 mph. I am a short man, and a good walker myself. I felt at times I was at a near jog to keep up. 

Signage led us on dirt roads toward Long Point. My feet really were beginning to hurt. I chatted on and off with folks. Mostly I focused on the finish. We had a few miles to go. 

There was still new trail to hike. We wound through brush and woods. Some body of water appeared off to our side. I think most of us were looking for the finish.

Finally, the Long Point parking lot — half a mile to go.

A sand path stretched before us. The day had turned from overcast to sunny and blue. I walked. Over a rise, the beautiful waters of the Atlantic shimmered gray and green like an oasis. A cool sea breeze blew. I looked out at the wonderful ocean.

We had made it.



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