Tackling the Cross-Island Hike

Plan ahead, but be open to surprises on this daylong journey.


It seems like every year, I plan to do the Land Bank’s Cross-Island Hike, and every year something comes up, a sore back, a sick kid, or just too many things to do. This year, I was determined to make it happen. I almost started from the beginning last year, but I’d gotten a terrible night’s sleep, and had the usual set of excuses. Instead, I joined the walk halfway, and went to the end for a total of about eight miles. That was easy enough, but the jump to more than 16 miles this year seemed daunting.

To make sure that I followed through, I declared my intentions on Facebook, and asked who else was going. I felt that I needed to prepare, to work up to it, even though I know that preparation is optional. Many people join on short notice, sometimes very short notice. Last year I met a woman who’d heard about it at an after-hours party in the wee hours of Saturday morning, then showed up for the hike at breakfast time. I’m not sure if she finished, but she came close.

William Veno has been organizing the Cross-Island Hike since 1998, and walks the whole way every year, along with many others. “There’s probably 30 or 40 people I see yearly or every other year or so,” Veno says, “and 20 to 30 of those do the whole thing every year.” He claims that it’s not an endurance event. “People are very resilient, and they’re very forgiving of me, and it’s just a lot of fun,” he says. “The real aim is to show people that there are a lot of trails out there that they can incorporate into their regular walks.”

The walk is broken into easy stages, with water and snacks at midmorning and midafternoon breaks, and a lunch stop where there is usually someplace to visit indoor plumbing. Still, it’s a long walk. The age range of the hikers is pretty impressive, something that was very much on my mind when my father, Woollcott Smith, declared that he was going to do the whole thing again. He’d done it a couple of times before, in 2007 and 2009, but for the past few years, every first Saturday in June has found him with something or other getting in his way. He’s in really good shape for his age (almost 78), but I was not convinced that this was a good idea for him. Still, we made carpool arrangements, and packed our bags.

On Saturday, June 1, I woke up at 4:30 am worrying about our new ducklings, and couldn’t get back to sleep. I fed the ailing duckling some electrolyte water and mash, then watered the garden, fed the chickens, the cat, and the dog, and got breakfast into Christopher, my 8-year-old. I packed a sandwich, trail mix, vegetables, and two oranges, plus of course a water bottle and a thermos of tea. At the last minute, I decided that Christopher would come with us. We set off with five people in the car to the starting point at Blackwater Pond Reservation, and we did not arrive early. Bill Veno estimates that about 140 people participated in all or parts of the hike this year, a record amount. We were at the tail end of something between 110 and 120 people who started the walk.

The moment we got out of the car, Christopher jetted ahead in the line to say hello to a dog, then to another dog, and so on until he was out of sight, which took all of about five seconds. Chasing after him, I lost sight of my father, whom I didn’t glimpse again until lunchtime, and then only briefly. I jogged up a good portion of the first stretch of trail, which according to my left Achilles tendon was not the best choice, but at least I managed to catch up with Christopher before we crossed the main road. Along the way I passed one other kid, whom I saw again later on the trail. It was all very sociable.

More people joined the crowd at the Tisbury Meadow trailhead, and a few dropped out at Wapatequa Woods. The plan was for Christopher to go home with his grandmother from there, but he wanted to keep going because he’d just found a strange round green object and was busy asking everyone what it was. Adult experts agreed that it was an oak gall, but Christopher came to a different conclusion. It was a dragon egg. In fact, he could see the baby dragon inside it. He regaled a couple with this tale, plus all of his knowledge of dragonology, for the next 3½ miles, at which point he started to slow down a little. My husband arrived to pick him up at the next stop, 7.7 miles into the hike, much of which he sprinted. I decided that it was OK if he zoned out in front of the TV for a while after that.

I trudged on. We reached the YMCA, where at least one hiker was quite unhappy with the fact that the cafe was closed, but most of us had packed our lunches, and there was water. The sun was shining through a slightly overcast sky, perfect weather for walking. Moleskin was passed around for blisters. I changed my socks. The hike resumed. We passed through the neighborhoods between the Y and Tradewinds, then crossed behind the Oak Bluffs School and over the marshes around Farm Pond to the beach. I’d lost sight of my father again, but he had a cell phone and was walking with other people. The second youngest hiker of the day was still with us. Brett Regan, age 10, is a fourth grader at the West Tisbury School. He was looking pretty tired by the midafternoon break, but he and his father powered through to the end.

When I reached the bridge just before 3 pm, my father wasn’t in sight yet, but sure enough, he came along 15 minutes later, moments after our ride home arrived. (Thank you, Michael Craughwell, for the two pickups!). “It was easy!” my father told Bill Veno. “That year we started at Menemsha and ended at Felix Neck, that was really hard.”

The following morning, I was tired but not utterly done in, and I had avoided blisters. The pain in my ankle was still there — though not much worse — and my thigh muscles were a bit sore. My father claims that he’s totally fine. The oak gall is deflated. It no longer looks like a dragon egg, but I won’t be surprised if Christopher finds another dragon egg, on another walk.

Next year, the Cross-Island Hike will set out from the Jaws Bridge, heading toward Chappaquiddick. You can join on a whim or train for months ahead of time, drop in or do the whole thing. I’ll see you there.