A three-day, 60-mile kayak trip from Rye, New Hampshire, to Portland in 1985 turned into a journey of a lifetime for four friends – a 32-year, 3,200-mile kayak circumnavigation of New England.

Tom Armstrong, Ben Pearson, Charlie Woodworth and I have been piecing together this dream a little at a time, 80 miles here, 150 miles there. Over the decades, family crises intervened and jobs changed, but we kept the dream alive, even during the few years we were not able create more lines on the map.

The idea evolved over the first few trips. At first it was to paddle the Maine coastline. After examining a map of the Northeast one winter we decided to paddle all the way around New England. Of course that meant completely encircling New Brunswick, Nova Scotia and the Gaspe Peninsula of Quebec. That was followed by paddling up the St. Lawrence River, then south through the Richelieu River canals, the length of Lake Champlain and continuing down the Hudson River to New York City. This last leg was completed in mid-October, a 120-mile stretch of the Hudson River from Hudson, New York, to the Statue of Liberty. We had paddled from the other direction to the Statue of Liberty from Old Saybrook, Connecticut, in 1993.

In October 2017, Ben Pearson and Tom Armstrong got a fresh look at the New York skyline, a somewhat somber moment seeing where the Twin Towers once stood. Photo by Michael Perry

Over the years, finding a pay phone to arrange end-of-trip pickup morphed into Googling weather forecasts and emailing trip updates by smartphone. Our beloved heavy wooden paddles gave way to lightweight carbon-fiber.

As beautiful as the scenery was, the folks we met along the way reaffirmed time and again that people are warm and caring everywhere. One afternoon, we crawled along the north shore of Nova Scotia’s infamous Minas Basin, home of some of the largest tides on Earth. We stopped at some simple shoreline cottages, selected a home and walked up carrying a bevy of empty water containers in need of filling. A smiling lady met us at the door, invited us in and proceeded to pull a blueberry cake out of her oven. We were amply fueled for the hard miles ahead against the current.

Every trip has involved pre-trip research and lots of phone calls to town halls, police stations and harbor masters in search of someone who might like to make some extra cash shuttling our vehicle to our intended end point. We have had a cast of characters help us over the years. One fellow was a prison worker in New York who was not much of a conversationalist. Another time, paddling along Northumberland Strait between Prince Edward Island and Nova Scotia, we hooked up with retired hockey player Bill Riley, one of the NHL’s first black players. Stories about his experiences made the drive back to his hometown an entertaining one.

In May 1993, Tom Armstrong patiently waits in his kayak as he watches the New York skyline as the Staten Island Ferry crosses his path. Photo by Michael Perry

One spot where we were lucky to have cooperative weather was the paddle around the northern tip of Cape Breton Island in Nova Scotia. As we left the fishing village of Neil’s Harbour, we hoped for light winds so we could take the direct route across Aspy Bay instead of following along the shoreline. Strong winds would have turned a 13-mile crossing into an 18-mile crawl along the shore. We surveyed the scene ahead, nearly mirror calm, and agreed to head across. Thirteen miles away rose the seaside cliffs of the Cape Breton Highlands, cast in a purple sheen in the early afternoon sun. One hour, then two slowly passed. After three hours, it seemed someone was towing the land away as fast as we were approaching it. The heights to our west looked no closer than they had when we began the crossing. After four hours we were finally within a few hundred yards of shore, and very thankful to get out of the kayaks and stretch.

We hoped that the perfect weather would last through the late afternoon because the cliffs we were about to paddle around offered no landing places. Indeed, it had the feel of a perfectly calm evening. Low alpine light wrapped the cliffs in gold. The deep, cold, clear Gulf water gently nudged the base of the rock fortress we were following along. Seabirds dashed out from their perches far above us as others came back from distant fishing forays. Fifteen miles to the north we spied the rock fortress of St. Paul Island rising resolutely out of the sea. The next land beyond St. Paul is Newfoundland.

Sure, there was a destination mapped out years before, but these four friends will always remember the journey. From left, Michael Perry, Ben Pearson, Charlie Woodworth and Tom Armstrong. Photo by Michael Perry

During the last leg of our circumnavigation, we spent an extra day in New York to visit the World Trade Center. It was sobering to walk around the Memorial to the 9/11 victims, their names inscribed on the square wall surrounding the footprint of each collapsed tower, water gently cascading down the walls below us. We took the elevator up to the observation deck for views up the Hudson that we had paddled down the day before, and up the East River that we had paddled down in 1993. Looking down at Ellis Island, Ben Pearson remarked that the sight was one of his highlights of the 32-year journey. He had come to “the realization that it was love, compassion, opportunity, and acceptance that made this country great.”

We felt very lucky to have gone on a unique adventure over so many years, blessed with special friends to share it with, and bound with the glue of unwavering family support. Tom Armstrong summed it up best as we departed for home; “We have paddled great distances, skied XC marathons, climbed tall mountains and biked Maine’s roads together, but it is the sharing of life’s challenges and opportunities which is most meaningful. Ours is a brotherhood shaped by a complete trust and respect for each other and a shared passion for outdoor exploration.”

Michael Perry is the former director of the L.L.Bean Outdoor Discovery Schools, and founder of Dreams Unlimited, specializing in inspiring outdoor slide programs for civic groups, businesses, and schools.

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