When Daniel Cooke left his high-powered position as a senior associate at Honigman to launch an outdoor adventure company in Metro Detroit, the reactions from colleagues were mixed — but mostly incredulous.
“I got a lot [of looks] when I left Honigman,” he says, laughing. “But my decision came from advice from my mom: Never quit something when it's going poorly. Pivot when you're in a really good space — when everything is at its apex, it's going well, and even in spite of that, you still decide, ‘Okay, but I want to venture out and try something new.’”
That venture became Expedition Detroit (expeditiondetroit.com), the region’s first full-scale guided hiking and outdoor experience company, with a mission as ambitious as its founder: to change the way people see Detroit, not just as a city, but as an outdoor destination.
Cooke’s entrepreneurial itch started young.
“I took a quiz in high school about what profession I should pursue,” he recalls. “My three answers were outdoor wilderness guide, park ranger and either lawyer-slash-entrepreneur. I remember thinking even then, ‘That directly aligns with my passions — but come on. You can't have a career in that. That's just fun time.’”
So, he chose law. He went to law school, landed prestigious gigs at top firms and worked in venture capital and intellectual property. But even as his legal career blossomed, something tugged at him.
“As I did more outdoor adventure travel throughout my twenties, there was always a voice in the back of my head, like, what could have been?”
That voice got louder. On hiking and rafting trips out west, Cooke met people who had built lives around the outdoors.
“They found a way to stay out there,” he says. “Now in their mid-to late-30s, they had found these entrepreneurial niches and built companies that were aligned with their passions,” he says.
So Cooke thought, “Why not Detroit?”
He saw a clear gap. “The ecosystem was all there, ski hills, the DNR, metro parks, mom-and-pop gear shops, advocacy groups — but it was very fragmented. No one was pulling it together or changing the mentality of this region of ‘we are an outdoor destination.’”
In August 2022, Expedition Detroit was launched full-time. The company offers curated, guided hikes across Southeast Michigan. From the trails of Pinckney and Proud Lake to corporate outings on Belle Isle, the experiences are built around showcasing the state’s natural beauty, often within 45 minutes of Downtown Detroit.
“We’re actually the largest provider of guided outdoor experiences in the entire Michigan State Park system,” Cooke says. “And we exclusively operate in Metro Detroit."
“There’s inherent value in discovering something new about a place that’s already familiar,” he says. “Some people just won’t go outside unless they feel safe — and that’s what we offer.”
Expedition Detroit also serves as a bridge for those who don’t see themselves in the traditional outdoorsy mold.
“A lot of people feel like, ‘I’m not that archetype — I’m not the guy in flannel,’” he says. “But they still want nature. We make it accessible. Otherwise, they may never experience that side of themselves. And in my opinion, that’s worth investing in.”
The company remains small — just five team members — but mighty. Their offerings include preset hikes based on SEO analytics and trending trail interest, plus tailored group experiences. “For individual hikes, people tend to head west to Brighton Rec, Pinckney, Highland,” he says. “For corporate groups, they usually want to stay close to the city. Belle Isle is our most popular.”
The company’s SEO strategy has paid off. “If you Google ‘skiing near Detroit,’ our article is the top hit. If you Google ‘Turkey hunting near Detroit,’ we’re number one,” Cooke says. “And none of that is sponsored. It’s all organic.”
That digital dominance is now translating into real-world demand. With perfect five-star reviews and a growing list of corporate clients, Cooke’s once-unlikely dream is gaining traction.
“We want to demonstrate that you can live in Metro Detroit, build a life here, have a family here, and still have immediate access to world-class outdoor experiences,” he says.
Cooke hasn’t fully left law behind. He maintains a legal practice on the side, but his passion is clearly with Expedition Detroit.
“I just felt like I wanted to do something more,” he says. “And it felt like I was at a point where I was either going to lock in and keep going that [legal] route — or take the risk and do something else.”
For Cooke, the risk is proving worth it, one hike at a time.
TRAIL TALES WITH DANIEL COOKE
Most Memorable Moment? For Daniel Cooke, two experiences stand out — one chaotic, the other deeply moving.
“The craziest thing? I led a group of five on a guided hike at Pontiac Lake’s rugged 10-mile mountain bike trail, walking the loop in reverse, as best practice dictates. Midway through, mountain bikers began wiping out left and right, flipping over handlebars on rocky slopes. One told me they were part of an adventure race: hike a mile, kayak a quarter mile, then bike the trail. I couldn’t help but laugh. That’s like jogging a mile, swimming four laps, then running a marathon! This adventure club just completely threw their participants into the gauntlet.”
A meaningful memory came during a night hike with a man named Ross, a first-time client in his 40s.
“He booked a night hike as a preliminary push into an outdoor lifestyle,” Cooke recalled. “At the beginning, he was timid. By the end, he was inspired, ready to explore more, plan trips. He was the epitome of the clientele we hope to have on the trail: people who are curious.”
Favorite Trail? Highland Recreation Area’s Haven Hill Trail often tops his list. “It’s about 3.5 miles, very manageable, but it has everything,” he says. “Wetlands with a boardwalk that makes you feel like you’re in Japan, rolling glacial moraine topography like the Appalachians and a rigorous incline leading to the old Edsel Ford estate ruins. Edsel called it his ‘nerve retreat'. It’s a piece of hidden history in the middle of Metro Detroit.”
Wildest Wildlife Sighting? In Maybury State Park during the fall rut. “We market our night hikes as ‘night hiking safaris,’” he says. “But this one — deer were cutting us off every 20 yards. Owls hooting, raccoons popping up — it felt like we were walking through a zoo. It was magical.”