On My Way: Cross-Island hike

Blue skies, sunshine, and birdsong for this year’s hike.


The birds sang from their hidden perches somewhere in the trees.

The songs rang out on the gorgeous day of abundant sun and blue sky, with a stirring of air in the soggy fields, throughout the wetlands ,and on the trail. The feathered friends were celebrating the oncoming summer, life and the soil of the earth, as were we. 

We were a group of more than a hundred from our starting point at the Hillman’s Point Preserve on the west side of Lake Tashmoo. The morning was promising in the spirits of those gathered, and in the clear sky and the light above the canopy of trees to the east.

The 2023 annual cross-Island hike ended a year ago at the east side of the Lake Tashmoo channel. In tradition, the following year’s hike begins where the previous one left off. Without boats to ferry us, trail leader Bill Veno chose Hillman’s Point Preserve, just across from last year’s end, as the 2024 start.

One of the wonderful things about the annual cross-Island hike, which has occurred annually on National Trails Day (the first Saturday of June) since the mid-’90s, and which is sponsored by the Martha’s Vineyard Land Bank, is that Bill does all the work. He spends about two weeks, he told me, coming up with the route, and then he leads the entire way. All the rest of us have to do is enjoy the walk.

The 2024 route took us onto 17 conservation properties and five protected ancient ways, with some roadwork. I consider myself active in the outdoors. Yet on this day’s approximately 19-mile hike, I knew only a few of the trails.

We set off from the beach of Hillman’s Point at the appointed time of 8 am. As a crowd we walked up the dirt road. We turned into the Phillips Preserve of Sheriff’s Meadow Foundation. We filed one by one down a winding switchback. Sunlight filtered through the trees. The adventure of the day lay before us.

We came out of Phillips onto the dirt road with Lambert’s Cove Road ahead. We walked up Lambert’s a short distance to the Ripley’s Field Preserve. Here Bill cautioned the group that there would be roadwork on this walk, and folks should stay to the side. A truck pulling a boat had left little space between the side of the boat and some of the walkers.

I fell into a conversation with local historian Tom Dresser. Tom is a well of knowledge of Island history. As we walked the quiet peacefulness of Ripley’s Field, Tom told me the story of Red Coat Hill.

Very simply, Red Coat Hill was used by the British during the American Revolution to look out over the water. A British soldier left his red coat on the hill, and so it became the name. 

We did not climb Red Coat Hill, but we did walk the ancient way of Red Coat Hill Road, following our route through Ripley’s Field, though I could not tell you where it began or ended. Prior to Red Coat, we had walked an ancient way called Shubael Weeks Road. 

The morning took us through a soggy, muddy field and across numerous wood-slat footbridges covered with lichen. One of the Island’s surprising little ponds sprung up to our left as we hiked through the woods. Somewhere, I heard the birds for the first time. They chirped and sang and whistled. Their songs came from the trees. I never actually did see one of the little creatures.

At nearly 55, I have noticed the songs of birds as if for the first time this spring. I hear them chirp through my window in the early morning. Their music, filled with wondrous notes, accompanies me on my usual early morning walk. The songs of birds have been a good discovery for sure.

Bill keeps a good pace. Signs for Blackwater Pond Reservation and Wompesket Preserve were at various trail intersections. Some terrain looked familiar.

We stopped to regroup at the trailhead of John Presbury Norton Farm — another property I had not yet explored — off Old County Road. We set off once folks had caught up. We turned from one trail to another. We came onto a hillside with scattered trees, and with a pond below. I was in awe of this little oasis. We traversed the hill back into the woods.

Somehow, we came out of the woods where the southern end of Lambert’s intersects with State Road. According to the itinerary, we had walked through the Manaquayak Preserve. Another new one for me. We took a short break at the West Tisbury Public Safety Building.

I walked with Kelly Joyce, an Island native and college professor, for the next segment. Kelly recalled how a farm had once been on her local road, and how kids played in the street without worry of traffic. 

We went through the South Indian Hill Woodlands Preserve, and then along the ancient ways of Rogers Path and Old Courthouse Road. The trail was rugged in sections and we passed an old cemetery. We walked at the front of the group with a few others.

In places, I heard the songs of the birds up in the trees. The sounds were sweet and full of life. The often high-pitched notes were melodies unto themselves. 

I caught up and walked with Bill for a while. Bill works with the Land Bank, and has been leading the walks since the late ’90s. I asked what made a trail an ancient way. Ancient ways, he explained, are old roads and cart paths. On some of these old ways, there is a public right of access, even when right through private property, though it sounded as though the legalities of establishing a right could be complex. Old Courthouse Road, Bill explained, derived its name because an old courthouse used to be at its end.

We came out of the woods near the Granary Gallery on Old County Road. We walked up County to the West Tisbury Road, and then turned toward the town center. A short while later, we sat at picnic tables and on the lawn, under the shade of big trees outside West Tisbury Town Hall, for our midday lunch break. We were about the 11-mile mark.

We all dug into what we had brought. The tuna sandwich, nut bar covered with dark chocolate, and orange in my lunch pack were delicious. I drank from my water bladder and took in the respite. The sun showed on the lawn outside the trees. I struck up a conversation with an amiable summer resident — also a college professor — whose name I never did get. 

Bill kept us on schedule. 

We started along Music Street after our allotted time. I walked a ways with the professor. We discussed the pandemic, and how libraries provided services. He had utilized his libraries’ services to aid in his research, and I had helped to provide such services as an aide with the Oak Bluffs library.

We walked up Middle Road to Tiasquam Valley Reservation. A pair of big oxen caught folks’ attention. We went into the trails of Tiasquam Valley, and looped around back onto Middle Road.

Soon we were walking alongside a brook running clear with cold, fresh-looking water. I had been here before, though I was not sure exactly where we were. The trail was knotted with roots and rocks. Kelly joked that the roots were massaging her feet. I responded in good humor that my feet were taking a thorough beating. We came onto Meeting House Road.

We crossed Middle Road to the Land Bank’s Tea Lane Farm property, where we walked up the side. Rows of flowers stretched in bright springtime colors the field’s length. A couple were out tending the land. The tide moved forward. There was little opportunity to take in the pretty scene. 

Back into the woods. Across the footbridge of a wetland’s area. Along one of those high rock walls one often finds up-Island. Then to the Middle Line Woods Preserve.

The birds continued to sing. I heard them when conversation stopped, or when I stopped to listen. Their songs of whistles and chirps floated magically and so audibly from the trees. There is much to celebrate, their songs seemed to say. Keep going, they said. There is joy in the woods. 

We had an afternoon break with water and snacks. I found a pack of peanut butter crackers in the bag Bill pulled from the woods. I dared not sit. My feet were sore and bruised, and blisters were forming. We had nearly five miles to go.

After the break, we climbed Peaked Hill (approximately 309 feet), and looked out over the sweep of the Atlantic Ocean and Vineyard Sound. We then descended, crossed Middle Road again, and entered the Fulling Mill Brook Preserve. 

Here, I realized the green of spring had been around us all day. On nearly every trail, green foliage and leaves had filled the trees and woods. The green was vivacious and radiant. The new leaves were supple and light. The birth of a new season was upon us. 

Fulling Mill Brook chuckled in the distance. We crossed the footbridge that climbed down and spanned a wetlands, and then we hiked back out and took the trail to South Road.

We walked determinedly up South Road and turned into the Chilmark Cemetery. Pickup drivers waited as we came out of the cemetery. But we were not done yet. We passed these folks, and crossed South Road into the Chilmark Pond Preserve. Down the hill we walked, and through the field. Onto the footwalk, and out onto the beach. There the 2024 cross-Island walk ended at water, on schedule at 3:20 pm. I looked at the pond for the first time, and marveled.

Folks who had completed the entire walk lined up to sign the book for a certificate. Some stepped off the footwalk onto the beach. A dog took to the water. The vibe was nothing but good.

On the way out, Kelly shouted congrats as she sat for a rest. I chatted with a woman in her 70s who had completed the entire walk. I fist-bumped Tom Dresser, who was coming down the hill. My son Peter waited for me up on South Road.

This year’s walk for me was one for the song of birds.


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