As I drove up to Pennywise Preserve last Saturday, I expected to see several other Island hikers waiting to join the pack. What I saw instead was an older man, sitting on a rock, legs crossed, no car, no bike . . . just by himself.

“Are you here for the cross-Island hike?” I asked. He smiled warmly and said, “Yes.” I informed him that I just heard the group was 45 minutes behind schedule, then worked on getting my backpack organized.

“Have you ever done a hike of this length? Are you able to do it?” he asked me.

“Oh yes,” I said, boasting a bit. I’m not a fan of anyone questioning my ability to do anything. “I’ve done some pretty challenging hikes in Utah, Wyoming and Alaska. Oh, and I run too.”

“Sure, but have you done a long hike recently?” he asked me.

I should say that I am somewhat guarded when I meet new people. When I lived out West one of the first things people would ask me was where on the East Coast was I from? Apparently I had an “edge.” I’m friendly enough, but don’t ask me too many questions, I’m not going to share very easily until I’ve figured you out. So when my fellow hiker started asking me a bunch of questions, I was admittedly a bit standoffish.

Soon after our introductions, I received a text from a friend who had been on the hike since the start at West Chop. He said they had fallen behind schedule and eliminated the Pennywise Preserve stop, and were now on an alternate route through the state forest.

And so began a journey which I now affectionately call Hiking with Herb.

An avid hiker of Island trails, Herb was confident we could meet up with the group if we hopped on the Dr. Fisher trail through the golf course and over to the Edgartown-West Tisbury Road. They were scheduled to take a break near Morning Glory Farm and he seemed sure we would make it there. I had planned to complete the entire cross-Island hike, an 18.2-mile annual journey led by the Martha’s Vineyard Land Bank. This year the route went from West Chop to Katama. Heavy rain and wind deterred me from hiking the morning route, so I was determined to make this second leg of the trek. I put on my raincoat and we started through the field into the woods, with Herb bringing up the rear. “You go ahead,” he said. “I’ll catch up.”

Alison Mead Herb Foster
The author, with Herb Foster. — Gary Mead

I love walking in the woods, and today was no different. The rain and overcast skies made the greens and rusts of the trail pop with color. Here and there I would stop for a moment and shoot a photograph, and look back to see how Herb was faring. I looked forward to meeting up with the group.

When we arrived at the Vineyard Golf Course, the trail split into three as we looked for the Dr. Fisher trailhead. Not well marked, Herb went with his gut and we continued straight, which soon led us to a residential area. Not familiar with this particular area, my sense of direction was completely off and my trust was entirely in Herb. While I wasn’t ready to admit it, I knew we were never going to catch up with the group and I was now on a completely different journey.

Herb Foster is an educator, administrator, writer, war veteran, widower and Boy Scout. At 84, he is in great shape. “I was in the infantry,” he said. “I’m used to walking.” Herb served in the Army during the U.S. occupation of Japan and was recently interviewed for a documentary about Nagasaki. He was married for 54 years. He holds the honor of having the longest Boy Scout membership in the country — over 60 years. An undergraduate of New York University and a graduate of Columbia University, he taught in the New York city public schools for almost 20 years, and ran Outward Bound programs for urban youth. If I was going to be on a journey with someone, I could not have picked better.

We walked for about half an hour through a nondescript residential area. At this point, I had no idea where we were or what direction we were heading. My cell phone battery was weak, but the texts that came through from my friend made it clear that we were close but not close enough. I started to feel frustrated. I finally suggested that we ask someone how to get to Morning Glory Farm. It turned out where we went straight, we should have gone left. Herb called his grandson Alex, and we got a ride to the intersection of Meetinghouse Way and Slough Cove Road.

“We just turned down a path called Swimming Place Path,” was the next text I got. It was raining hard now and Herb and I were soaked. We stood in the rain for what seemed like an eternity, peering at our soggy, deteriorating map, trying to decide what to do next. A text came through with a GPS map pin pointing exactly where the hikers were, but with the rain and my dying ancient cell phone, the best I could do was forward it to my father, who lives in Katama, to make sense of their location.

“I just passed the hikers — I’m coming to get you,” my dad said on the other end of the phone. I felt like we had been saved. We had only hiked about 4.5 miles, but the journey seemed endless. My dad pulled up in his big old Country Squire station wagon, his dog excitedly jumping around in the back.

“Dad, this is my new friend Herb,” I said.

“The hikers are passing the Right Fork Diner now,” my dad said. “We can catch them!” Like me, my dad had planned to do the entire cross-Island hike that day but was put off by the heavy rain and wind. We barreled down the road past the diner and Katama Farm, as Herb and I wiped condensation from the windows and tried to locate the hikers in the field. “Where are they?!” I said, frustrated.

katama point preserve
Mr. Foster hikes toward finish at Katama. — Alison Mead

We drove to Katama Point Preserve where the hike was supposed to finish. “What now?” I said. “Maybe they are walking along the beach to the point,” my dad said. I looked at Herb. “We’ve come this far, we might as well try to meet them,” I said. The wind and rain were wicked as we walked the path. I shot a quick photo of Herb making his way to the finish, and ran to catch up with him. I imagined seeing the hikers making their triumphant last steps, but when we got to the beach there was no one.

Defeated, Herb was ready to call for a ride — but my dad was still waiting in the Country Squire, not willing to give up. “Let’s go back to the trail and see if we can meet them — they may have had a tough time crossing the field,” my dad said.

We waited, soaking wet, for the hikers to emerge. And then, with a glimpse of orange we saw them. I jumped out of the car to see my wet and weary friend who had been texting me. “Hey! We found you!” I exclaimed. More soggy hikers emerged from the path. I shielded my camera from the rain and photographed the hiking heroes. We made our way through Katama Point Preserve and the hardy hikers reached their final destination. High fives and hugs all around.

As we walked back to the road, Herb and I were no longer a single unit — we were part of the pack. Cars lined up at the trailhead waiting to pick up the hikers. “Herb, wait, wait!” I said, “I want a picture of us.” My dad snapped a quick shot with his phone and my almost five-mile Hiking with Herb adventure was over.

Later that night, in warm, dry clothes, a big plate of pasta in front of me, I posted the photo on my Facebook page. “I love how the love of nature and adventure can turn strangers into friends,” commented a friend.

Me, too.