Bill Veno has been leading the Martha’s Vineyard Land Bank’s cross-Island hike each year since 1998. The only years he missed were two during Covid, when the hike didn’t take place, and one when he had kidney stones. Otherwise the senior planner at the Martha’s Vineyard Commission has been at the front of the pack each year, introducing Islanders to the vast array of trails that crisscross the Island.

This year’s hike takes place Saturday, June 1, beginning at 8 a.m. at Hillman’s Point at Lake Tashmoo. The full trek is just over 19 miles long, ending at the Chilmark Pond Preserve.

“It’s amazing how much its grown over the years,” Mr. Veno said. “It used to be about 40 people, with 20 or so finishing the full hike. Since 2014 it’s really blown up to over 100 each year. A lot of people say they look forward to it all year.”

The hike always begins near where the previous year’s hike ended. The trail is mapped out beforehand, working hard to introduce participants to trails they might not be familiar with and that take into account the variety of the Island’s topography.

“We try to hop and skip along different conservation properties,” Mr. Veno said. “This year we have to walk along some roadways too. We don’t have trails everywhere yet, but we are getting close.”

While participants do not literally have to hop and skip, hikers should prepare for a brisk pace, Mr. Veno said.

“I’m very tall and so have a long stride,” he said. “But we pause now and then and I advise people to recognize their limits. We like people to enjoy themselves and not over-exert themselves.”

Hikers don’t have to complete the entire route, Mr. Vino added. There are many spots along the way to arrange a pickup by car.

An experienced guide, Mr. Veno has his pre-hike strategy down to a science.

“I walk my dog a lot,” he said.

For more information, and detailed look at the route, visit