It was the first Saturday of June, National Trails Day, recognized by the Martha’s Vineyard Land Bank with an annual walk from one side of the Island to another.

I have participated in the Cross-Island Hike at least 15 times, and in 2022 walked 60 miles on the West Highland Way in Scotland with my daughter Jill. But at 77 years old, at the end of each year’s hike I mutter: “This will be my last one.”

But come June, I lace up my boots, happy to be exploring the Island again one step at a time.

Bill Veno (center with red cap) led the way. — Courtesy Tom Dresser

Bill Veno leads the hike, compiling a different route each year to allow hikers to explore varied conservation sites — and perhaps to keep hikers on their toes as to which way to go.

Saturday dawned with a brilliant sun in a cloudless sky, atypical of the previous multiple rain-splattered weekends. Janet Holladay counted off 99 hikers who gathered at Hillmans Point Preserve on Lake Tashmoo in Vineyard Haven, ready to face a grueling 19.3 miles walking up hill and down dale.

The first .31416 miles are the easiest; the subsequent 19 miles can be tough.

Many hikers elect to walk only part of the route, which leaves them with a taste for the charm of Island walking, but without the ceremonial gold sticker which certifies completion of the annual trek. I take pride in my gold stickers but have no idea where they are now.

The beauty of the Island on foot. — Courtesy Tom Dresser

Bill Veno is very tall, a certified moon-fixer, with an average stride that is three-times that of the average hiker. In other words, he sets a fast pace. Along the way, he ties little pink ribbons at turns to show the route, while a land bank guide at the end of the group herds slower walkers along and removes the ribbons.

The first few miles through Ripley’s Field, Wompesket Preserve and John Presbury Norton Farm were delightfully easy-going walks along shaded trails. Nancy Weaver passed out chocolate at the brief break at Ice-House Pond (aka Manaquayak) and a full break was savored at the West Tisbury public safety building.

After eight or so miles, it was relaxing to sit down on the grass and catch our breath for about seven minutes. Back on the route, hikers kept up a steady pace. No one threw hiking sticks or water bottles at one another; it was a congenial group marching onward.

Several canine companions were part of the entourage and seemed to enjoy one another’s company, as well as the unique odors along the trail.

The author at rest. — Courtesy Tom Dresser

Lunch was scheduled for noon at the West Tisbury town hall, and captain Bill Veno beat his own schedule getting to the halfway point three minutes early. It was gratifying to sit down, remove our footwear and enjoy our lunch break. But before long we were back on the road, along Music street to Middle Road, up and over to the Tiasquam Valley trailhead.

That was tough, with no rest for the weary, though some people had enough and peeled off. Then it was onward along a charming brook to Meetinghouse Road and on to the Island Folk Pottery.

Although level, the stroll through the Middle Line Woods Preserve proved a challenge for aging knees. At the afternoon break, your reporter had to lie down on the ground. It was either lie down or call it a day.

Too soon we found ourselves marching up and over Peaked Hill and on to Fulling Mill Brook. Many hikers picked up the pace, like horses realizing their barn was nearly in sight. Then it was along King’s Highway and on to Abel’s Hill. Another half-mile downhill to Chilmark Pond was required to sign the book as proof we had walked from Tashmoo to Chilmark Pond.

Bill Veno handed out gold stars and Wendy Goldfarb said she was looking forward to seeing us again next year. Then it was time to hike back up to South Road and catch a ride home, soaking sore feet and savoring precious memories.

It was a rewarding hike and well worth the effort. This year I didn't even find myself muttering at the end that it would be my last one. Next year, I will definitely be back. 

Tom Dresser lives in Oak Bluffs, where he walks and writes with his wife Joyce.