Seek the Peak Spotlight: Ryan Shepard

By MWOBS Staff

Before Ryan Shepard moved to Conway, he was in Western New York celebrating his 40th birthday party.

“I wanted to go big,” he said.

“Big” meant setting up a fundraiser for a local pitbull rescue foundation. He booked a restaurant and music venue, lined up three breweries and two distilleries, organized a silent auction and walked away having raised over $1,300.

Not your typical 40th birthday bash, but Shepard was spending the day doing what he loves.

That was four years ago. Soon after, Shepard moved to Conway to take a management position at REI. At the time, he didn’t know much about the Mount Washington Observatory.

“When I first moved here, I had no concept that the observatory was even here,” he said. Once he got the full story, he signed up for Seek the Peak immediately.

This summer marks Ryan’s fourth year participating in Seek the Peak, the Mount Washington Observatory’s annual hike-a-thon, and the third year with his team, Fire on the Mountain—named after the Grateful Dead song (of course). Ryan has become one of the event’s most inventive and committed fundraisers, dreaming up new ways each year to bring the community along for the climb.

Fundraising that doesn’t feel like fundraising

Over time, Shepard has learned that the most effective fundraising doesn’t feel like fundraising at all.

“If there can be some sort of experience,” he said, “there’s a give and take. The folks who are helping you were already coming out to eat or grab a beer with friends. You’re just giving them a way to take part.”

That idea shows up in everything he organizes. A dine-to-donate night doesn’t ask someone to carve out extra time, it just gives them a reason to spend their night out at Tuckerman Brewing Company. An ice cream stop at Trail’s End becomes part of something larger. A tattoo becomes a shared contribution instead of a personal decision.

Instead of asking people to stretch their time or their budgets, Shepard builds opportunities that fit into what they’re already doing. It lowers the barrier to becoming a supporter of Seek the Peak and extends the event beyond those who plan to hike.

“It’s a lot of legwork,” he said, “but I don’t mind doing that. To me, that’s fun.”

Understanding the audience

In a region where both locals and visitors move through the same small network of businesses, word travels differently.

Shepard puts flyers in storefronts, stops by hotels and asks if they’ll leave information at the front desk, and looks for any other opening he can find. This year, after spotting an opportunity at a community gala, he arranged a spot on the morning show at Magic 104 to promote the fundraiser to the Valley’s wider audience.

Timing matters, too. After holding the tattoo fundraiser in April last year, Shepard adjusted the date to better align with the start of summer traffic, when more visitors are in town looking for something to do.

It’s not just about reaching more people. It’s about reaching them at the right time.

The more creative, the better

“How creative can you make it?” he said. “Because that’s what’s going to draw folks in.”

Shepard has always aimed to organize outside-the-box fundraisers, including a mini polar plunge at a bar where he used to work. Every $100 raised, a bartender would jump into a kiddie pool full of ice on the back deck.

One of the main events of his Seek the Peak fundraising is an annual tattoo event with Night in the Forest Tattoo in Intervale. The designs are pre-drawn—mountain landscapes, weather imagery, hiking scenes and any other imagery that would resonate with someone who spends time above treeline—and the proceeds go to the Observatory.

The more engaging something feels, the more likely people are to stop, ask about it and decide to be part of it. Even if they’re in Intervale—miles away from Mount Washington—getting a small tattoo on their ankle now makes them part of the community that supports the Mount Washington Observatory.

Time to Climb

By the time Seek the Peak arrives, much of the fundraising work is behind him. Now it’s time to enjoy the day with his team.

“I love being up on the summit once again saying, ‘Hey, I made it up here,’” he said. “I’m not an athlete. I’m not running ultramarathons. But I’ll do just about anything for a good cause.”

Every year, somewhere on the descent, he swears it’ll be his last.

“Every year I go, ‘You know what, next year I’m still going to fundraise, but I’ll just volunteer down at Great Glen Trails.’ And then I do it again.”

What keeps pulling him back is simple. He believes in what the Observatory does, and he wants to be part of making sure it continues.

“I am super excited for this year’s Seek the Peak,” he said. “I think it’s going to be fantastic. If you see me there, feel free to say hello and introduce yourself. We’ll bond over our sore muscles together.”

Ryan Shepard’s team, Fire on the Mountain, is currently on the Seek the Peak 2026 Leaderboard! To learn more about their team, click here.