Westminster native joins Annapolis man on 700-mile kayak trip

Chesapeake Conservancy's Kyle Smith, left, and Conor Phelan paddle out of Brown's Cove near Greenbury Point on Saturday morning.The two are preparing for their 700 mile kayaking trip in Alaska in June.
Chesapeake Conservancy's Kyle Smith, left, and Conor Phelan paddle out of Brown's Cove near Greenbury Point on Saturday morning.The two are preparing for their 700 mile kayaking trip in Alaska in June.(Matthew Cole / Capital Gazette)

In just two and a half weeks, Conor Phelan, of Annapolis, will leave from Ketchikan, Alaska for a 700-mile kayak expedition, expected to last the entire summer finishing at the coast of the West Chichagof-Yakobi Wilderness Area, home to Freeburn Mountain, named after Phelan's great-great-grandfather.

While Phelan braves the Alaskan wilderness — from dangerous tides to cold weather to bears all in the name of his family legacy — he will be joined by Westminster-native Kyle Smith, who will face all the same dangers, but on a journey with none of the familial significance.


Phelan said he asked a number of folks to join him on this extended personal expidition, but was turned down again and again. Smith said when Phelan asked to join him on the kayak trip of a lifetime, it barely took any thought at all to agree.

"Conor's got this whole family thing going on that gives him a connection to Alaska," Smith said. "I don't have any of that. The Smith clan doesn't have any connection to Alaska whatsoever. All I've got is a passion for travel."

In the early 1900s, Phelan's family lived throughout southeast Alaska, with his great-great-grandfather William Freeburn managing the Chichagof Mine. Phelan said he came across photos taken by his great-grandfather throughout the region, which has since been designated as a preserved national forest. It was while looking through the photos that a plan for the kayak trip began to form.

He would travel the land where his ancestors lived and recreate the photos taken by his great-grandfather more than a century earlier. Phelan began to look at the logistics of the trip and plan what it would take to visit the mountain, which is located in a Wilderness Designated area, the highest level of federal protection of any land type.

"It's completely untouched, there are no roads, no trails, nothing out there," Phelan said. "The other side of that coin is that it's amazing to know that down the road, generation after generation, it will remain in the same pristine state it is now."

The 700-mile journey takes the two travelers by kayak along the coasts of a number of Alaskan islands, clustered together on the southern end of the state. The trip will last the entire summer, with the pair carrying all of their gear along with them. Phelan said they're anticipating going at least three weeks at a time completely separated from society, with occasional stops into small communities of less than 100 residents each.

Phelan said because of the isolation, and the potential danger, his mother made him promise he wasn't going to take the trip alone.

"I went around pitching the idea to people I know, but nobody was biting," Phelan said. "Eventually I mentioned it to Kyle, who I work with [at the Chesapeake Conservancy], and the plans started to hatch there."


While Phelan has backpacked in the Alaskan wilderness as part of a National Parks Service botany crew, it's Smith who is providing the kayaking expertise for the pair.

In the past, Smith kayaked for two weeks off the coast of Washington state in weather conditions similar to what the pair will experience in Alaska.

"I've got the knowledge of what it takes to set up every day and pack up everything you need," Smith said. "It takes a special person to know how to live out of a kayak for two weeks or more."

According to Smith, there is one potential danger on the trip that his experience in Washington did not prepare him for.

"The island that we're going to be on, Chichagof island, when I started to look it up, I discovered that is has the most brown bears per square mile of anywhere in the world," Smith said. "Most of our hiking we're going to be doing is using brown bear trails to get around the wilderness, so that's probably the most unnerving thing about the trip. We're going to be vastly outnumbered by bears."

Smith said he's been kayaking his entire life, with frequent trips to the Chesapeake Bay to practice his paddling skills over the years. He said his family has long held a passion for the outdoors and being a part of nature. His trip to Alaska, he said, is just one in a long line of elaborate family journeys.


"My older brother spent time in Egypt and Jordan; my dad's been all over the world," Smith said. "When I approached them about this, they were not as shocked as I thought they'd be. They were relieved we were level-headed and have our plans set out for us."

Preparation for the trip had to be started early. Because the pair will be separated from civilization for at least three weeks at a time, and will be restocking at sparsely populated Alaskan towns, they are currently in the process of packing and shipping boxes of food to each of their stopping locations so they can stock up for the next leg of the journey.

In the fall, both Phelan and Smith will start grad school, with this summer trek representing a culminating journey before the rest of their lives begin. During the trip, the pair decided to leave one last gift for the Chesapeake Conservancy, by starting a fundraising campaign for the organization. Donations can be made at https://www.fortua.com/campaigns/700-mile-kayak-journey-to-raise-funds-and-awareness-for-a-healthy-chesapeake-bay.

So while Phelan travels the Alaskan coastline, retracing the steps of his great-grandfather and reconnecting with his sense of self, Smith will be along for the ride, supporting his friend and coworker. Though he may not have the same family connection to Mount Freeburn, he said he knew he had to join Phelan on this journey.

"My parents have both been world travelers, and every place they go and have spent time, they say they've picked up something valuable that they've carried with them the rest of their lives," Smith said. "Growing up with them, and having that instilled in me is so important. I'm going to gain more knowledge, more experience than you could ever get working in an office or staying in one place. If I turned it down, I'd never let myself live it down."