Kayak Connection

  • Shepherd became the executive director of Rippleffect in 2015.

  • Bessie greets people as they arrive at Cow Island.

  • A group of teenagers paddles around Cow Island.

  • A camper climbs the rockwall.

  • A preteen boy is about to embark with his group on a sea kayaking trip.

For Rippleffect executive director Adam Shepherd, outdoor education is a path to leadership skills.

When Adam Shepherd was in college, his plan was to join the music industry. He even worked in Nashville for two years as a recording engineer, snagging credits on Brooks and Dunn and Neil Diamond albums. Then he went on a backpacking trip. “It railroaded my career plans,” he says.

Now, the 41-year-old South Portland resident wakes up five days a week and commutes across Casco Bay to Cow Island, where he oversees local kids as they kayak, swim, and zipline in the name of wilderness education. Rippleffect, a youth development and leadership program, is “not just about teaching kids to kayak and tie knots,” Shepherd says. “It’s about compassion and social emotional development.”

Rippleffect was founded in 1999 as a way of helping young Mainers connect with the ocean so close to where many of them grow up. Two years later, the nonprofit bought 26-acre Cow Island with the help of the Maine Coast Heritage Trust and the community. The program now serves 3,500 students, ages eight to 18, each year through a series of camps and school programs.

On a Tuesday morning in July, the sun is beating down on the island as the temperature climbs into the high eighties. The heat is exhausting, but the kids are bubbling with excitement. Shepherd matches their enthusiasm as he helps the 12-year-olds drag brightly colored sea kayaks down a rocky path to the shore. The day-campers laugh with him as he and the guides help them into the narrow boats before they head out into Casco Bay. They exude a nervous, excited energy as they prepare to make their loop around the island. Shepherd’s smile cuts wide across his face as he pushes each kayak out to sea.

Helping kids launch their kayaks isn’t exactly in Shepherd’s job description. Neither is spotting them on the rock climbing wall or overseeing games on the ropes course. Although being Rippleffect’s executive director keeps Shepherd more than busy with big picture ideas and growing the organization, he can’t help but engage with the kids as they explore the island and learn to interact with nature. It is, after all, what drew him to the organization. “I’m a recovering guide, so I still love to get out there,” he says.

Prior to joining Rippleffect, Shepherd worked for over a dozen years as a summer camp director before moving to Maine in 2012 and becoming an outdoor guide on Cow Island. By the following year he had been promoted to Rippleffect’s director of advancement. When the executive director role became available at the end of 2015, Shepherd “jumped at it,” knowing it was the opportunity of a lifetime. “It’s my dream job,” he says. “I hope it’s the last job I ever have.”

Being executive director means Shepherd needs to recognize where Rippleffect can and should do better and then figure out how to make that happen. The organization’s biggest growth area needs to be lowering the barriers to outdoor education for Maine students, he says. “We exist to provide every child in Maine with an outdoor experience regardless of barriers, whether they be social, economical, cultural,” Shepherd says. As Maine’s demographics diversify—especially in Portland—and more immigrants come to the state, making Rippleffect more accessible has become a bigger focus. The organization not only gives scholarships, but it also works with schools to bring students to the island. There are 28 schools that take field trips to Rippleffect each year, including every middle school in Portland. Additionally, each fall the Casco Bay High School freshman and senior classes spends a week on the island.

Getting kids together outside of school and away from screens and technology is important, Shepherd says, because it helps them experience deep “human-to-human connection.” Working together through problems, such as how to get a group from one tree to another using pieces of rope, and participating in discussions about leadership styles, allow students to better understand each other and themselves. While what constitutes adventure depends on the individual, Shepherd says the more remote an experience, the more meaningful it can be. For example, the girls’ leadership camp, a week-long program for teenagers, involves the group getting to know each other for a couple of days on Cow Island through structured discussion and activities before heading out to camp. As a group, they kayak to different islands throughout Casco Bay, set up camp for a night, and head to a different island the following day. “That depth of wilderness experience is where we see the group bond and build confidence,” Shepherd says. “We see this being critical for human development.”

Whether kids participate in a day camp, school trip, weeklong camp, or a 12-day leadership program, the goal is for them to develop as leaders. Shepherd says Rippleffect works to teach young people how to contribute to the global community and to be stewards of their own communities. “If it stops here and doesn’t get carried over to the mainland, we’re not doing our job,” he says. Connecting with others and with the land and water near where they live teaches kids the impact they can have on the world around them. And if they’re anything like Shepherd, the experience will hopefully “railroad” their career goals in the best way possible.


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