There’s a guy on Smith Island, Maryland whose life seems tiny and huge at the same time. His name is Tim, and his lineage goes back a dozen generations on this little patch of turf that peeks out of the Chesapeake Bay right at the Virginia border. Tim hardly ever leaves Smith Island. He knows where he belongs and who is is: a master forager, amateur archaeologist, and keeper of the flame of island memory. He’ll tell you in his  unique island patois that he’d rather focus on the past than the future, and he’d rather stay in his own watery backyard than cast his net  into the wider world.

When my husband, Jim,  first suggested we visit Smith Island (which was named for Captain John Smith, who reportedly went there in the 17th century) I was less than enthusiastic. It’s an hourlong boat ride across the bay from the Eastern Shore mainland town of Crisfield, and I make no bones about the fact that big water scares me. But I agreed to go, so that was that. The crossing happens once a day. Pilots Big Terry and his son Little Terry live on Smith Island, and every morning at 7:30 they motor over to Crisfield in their cruiser,  which to me looks like a converted fishing boat, about 25 feet long. They return at 12:30 sharp, and if you want to ride along, it will cost you $20. You’ll probably be sharing the ride with boxes of groceries, piles of lumber and hardware, and usually at least a half-dozen people, nearly all of them residents. Only about 350 people live there, and not all of them full time. The only way to get the supplies they need is by boat. So the two Terrys make their living ferrying goods and folks back and forth, in all kinds of weather.

Fortunately for us, the October day dawns sunny, and as we climb onto the beat-up little boat, I relax a bit. It’s standing room only, so I lean against the grocery boxes and listen in to the conversations around me as we bump across the channel. There are a couple of middle-aged women on board, both of whom now own cottages on the Island, but are from somewhere else. They lament the loss of one of their neighbors, an old man who had died suddenly. I learn there are only three communities on Smith Island, and absolutely everybody knows everybody. The ladies start talking about an art show somebody wants to put on, and they wonder if there will be enough people on the island to make it worth the effort. Inside the boat’s cabin, there’s a little boy and a woman who looks to be his grandma. The boy acts like he’s made this crossing a hundred times, just like the rest of the passengers.

As we putt-putt into the town of Ewell, our destination, I notice the infrastructure of the port looks none too sturdy. The docks are missing slats, the buildings are unpainted, and some of them are falling into the water. Grass grows tall in and out of the shallow water. Tackle is piled up everywhere, and empty crab pots are stacked high. When we disembark, Michelle, the host of the Smith Island Inn, is waiting for us with her golf cart. It takes about five minutes to tour the town, and we settle in at the three bedroom B & B. We are the only guests, and the house is inviting  and clean. Michelle shows us where the bicycles are, and reminds us that we have an appointment for an island tour with Tim in about an hour. Since the only restaurant closes at four when we’ll be out on Tim’s boat, she assures us she’ll pick up our crab cake and coleslaw dinners and bring them to the house, where we can eat them later.

You don’t need gears on your island bike. The terrain is completely flat, and some is under water. In fact, as we cycle down the road, we have to dodge large puddles, and there is standing water in most people’s yards. Mosquitoes are  a torment, and we try to outrun them on our bikes. In a couple of minutes we’re on our way to Rhodes Point, which is really just a few houses and a couple of dilapidated docks. The view over the water is spectacular though, and it’s so quiet you can see the appeal for solitude seekers. But again, there’s so much water lapping at our bike tires that I can’t help but think living here would be very dicey in a storm. And it doesn’t take much imagination to see this island vanishing into the Chesapeake, taking its centuries of history with it.

Tim has strong opinions about the future of Smith Island, and for the next couple of hours, he will explain by – quite literally – taking us back in time. Inside his little museum next door to the Cape Cod style house he grew up in, are dozens of neatly framed displays of native spear points. Since he was a boy, he has combed the miles and miles of shoreline looking for artifacts, and he’s found thousands of them. In fact, he’s educated himself so thoroughly on the subject, he’s considered an expert by the Smithsonian. He shows us specimens he claims date back nearly 13,000 years. To Tim, this is proof that the area was inhabited far earlier than most people think. It’s really a dazzling array, lovingly preserved and categorized by area and material and date. Pretty impressive. He also has on display two “long guns,” which are eight-foot-long rifles that were outlawed early in the 20th century. Why? Because one shot from one of these beauties could bring down three dozen birds. Hardly a fair fight. Tim says islanders kept on doing it for decades after it was made illegal. After all, who’s watching all the way out in the middle of the Chesapeake Bay?

After the museum, we cycle down to the dock, and hop into Tim’s open fiberglass power boat, probably 18 feet long or so. Tim’s had his own boat since he was a kid, of course, and he knows every inch of every channel deep enough to allow the boat through. There are hundreds of miles of shoreline here. It’s not beach; it’s grass, and Tim weaves his boat through the maze as if he’s been doing it all his life, which, of course, he has. He takes us to a spot where we can  look for arrowheads and sea glass. How he can tell one spot from another is beyond me, but we jump out and start hunting. With Tim’s guidance, I find an arrowhead, and I’m so excited when he tells me it’s an “antiquated point, between 4,000 and 5,000 years old.” Cool. We collect some old bottle glass too, which Tim assures us is from 19th century settlements that have since disappeared into the bay.

We follow up our hunt with a thrilling cruise through the wildlife refuge, which is part of the island. We see flocks of pelicans and other seabirds, and it’s so beautiful and full of life, we find ourselves grinning from ear to ear. We’ve heard that erosion is a huge problem for Smith Island, but Tim doesn’t seem too worried. He believes the tides just move sand and soil from one spot and deposit it in another, over and over and over again. He does worry about the dwindling oyster and crab populations though, and as he sits at the helm of his boat In white rubber boots, torn t-shirt, plaid jacket and baseball cap, he speaks of the fragility of nature in surprisingly poetic language.

When we get back to the inn, our dinners are waiting. I have no doubt the crab was caught that morning; it is the freshest, most delicious crab cake ever, and probably the best meal I’ve ever had on a paper plate. We follow it up with some Smith Island Cake, which is actually famous. It is between 8 and 15 layers of yellow cake, with icing between each layer. It’s delicate and sweet, and I’m glad I can’t get my hands on it where I come from.

Too soon — at 7:30 the next morning — we are back on the boat with the Big and Little Terrys on our way back to the mainland. It’s a bumpy ride, but I forget all about that as soon as I start talking to an island resident who spent her career in the foreign service. She lived in Iraq and Africa and Pakistan, and retired a decade ago to raise her daughter on Smith Island. The girl attended Ewell School, with fewer than a dozen other kids, and is now kicking butt at a prestigious private college in Annapolis. To my astonishment, this lady is an ardent democrat, and I find myself once again reminded of the most important lesson of traveling: Throw your pre-conceived notions out the window.  You absolutely never know who you’re going to meet in the middle of the Chesapeake Bay.