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Elissa Turnbull

4.15.25

How to Walk Across Martha’s Vineyard

If you ever wanted to traverse the Island in a day, Bill Veno can show you how. Follow his advice and you may discover new parts of the Island that you’ve never seen before.

On February 10 of this year, Bill Veno celebrated his sixty-eighth birthday. For those who know him as the organizer of the Martha’s Vineyard Cross-Island Hike, it was no surprise that he spent the morning out on a walk with his dogs.

“They keep me going,” he said. 

But Veno may be exaggerating a bit – he doesn’t seem to need much encouragement to go out for a walk. For twenty-six years, Veno has been planning and leading an annual, all-day, varied-terrain, briskly paced, often nearly twenty-mile hike across the Island. Each year, the route is different. Each year, it’s a challenge. 

How does he do it? And why does a dedicated group, sometimes totaling one hundred or more, gather to follow in the very wide gait of the six-foot-four-inch hiker? Maybe because it’s a good excuse to test one’s endurance or to see new parts of the Island. Or maybe it’s because we’re all searching for a trustworthy, benevolent leader to guide us through the wilderness. 

Elissa Turnbull

Veno, originally from Michigan, moved to the Island in 1997. He was the Martha’s Vineyard Commission’s senior planner and a trail planner for the Martha’s Vineyard Land Bank Commission until he retired last year, although he still works part-time planning trails for the land bank. 

The Cross-Island Hike began in 1993, when the land bank learned of the newly-created National Trails Day. John Potter, the land bank’s land superintendent at the time, suggested a hike that spanned the Island to mark the occasion. 

One of the reasons for the hike is to encourage people to spend more time outdoors. 

“There’s a PR thing as well for the land bank,” Veno added, “to kind of show off the properties and the trails that went through them. But then, also, to show how it was possible to have extended walks.” The long hikes, which also include properties belonging to the Sheriff’s Meadow Foundation, The Trustees of Reservations, and towns, helps to “emphasize the connectivity” of the preserves, he said.

In 1998, Veno began planning the hikes. Drafting the route each year is a feat unto itself. He considers whether there are any new properties to show off, then finds ways to connect trails, easements, ancient ways, public paths, and regular streets to form an unbroken chain. For the past decade, the hikes have begun about where the last one ended.

Elissa Turnbull

This creates a “continuous ball of string that wraps around the Island,” Veno said, which further underlines their interconnectedness.

This year’s hike will begin at the Chilmark Pond Preserve, but Veno is still planning where the group will go from there. One important consideration is where to stop for breaks: Veno finds places for morning, lunch, and afternoon pit stops. He also refers to Vineyard Transit Authority bus stops so walkers can arrive and depart without dealing with parking. He aims for a total length of seventeen to twenty-one miles that can be covered in about seven hours.

Before the day of the annual hike, Veno checks out parts of the route to make sure they’re accessible. But he does the full walk for the first time on the day-of with the other participants. 

On the day of the event – Saturday, June 7, this year – hikers gather rain or shine. The crew that shows up is a varied mix. Some come to hike just a portion, dragging along friends who give them the side eye. Some come every year, ready to go from morning until afternoon. But not everyone comes dressed to impress. “I’ve been amazed at people who have shown up in flip-flops, which I don’t recommend,” Veno said. “But they’ve done the entire thing.”

Some other advice: “Be prepared,” he said. “Be a Boy Scout or Girl Scout.” Water, sunscreen, and snacks will be helpful. Rough terrain, weather, and ticks will be encountered – as will other surprises. 

One year, Veno checked out a section of the trail ahead of time. But when the hike date rolled around, spring had fully sprung. 

“I was leading the walk through all this blueberry and huckleberry that had grown together over the trail and I was like Pig Pen kicking up the pollen,” he said. “I turn around and everyone’s just covered in this yellow-green powder.” 

About ten years ago, it wasn’t pollen in the air but a winter moth infestation. Thousands of caterpillars were hanging down from the trees on their silk. “It looked like a horror movie,” he said. He had to wave a stick around in front of him to clear the way, “like in an Indiana Jones movie.”

The best leaders not only blaze a trail but also inspire teamwork in their followers. One year, when the group was caught in a high tide while rounding a point at Great Rock Bight in Chilmark, things got dicey. “We had to do a ladder of people to skate across the cliff face and the water was splashing,” he said. 

This year, Veno will miss leading the group for only the second time since 1998 to attend his fiftieth high school reunion. Tony Lima, crew manager with the land bank, will be in charge. Veno’s planning and Lima’s presence will be there to guide hikers through breathtaking Island bights, bluffs, knolls, and dells. Come prepared for the unexpected, including the unexpected feeling that you can do it.