Underground Donut Tours: From Side Hustle to Sweet Success

Jeff Woelker sits atop a donut empire.

In 2015, this aspiring entrepreneur launched the Underground Donut Tour in Chicago, offering guided walks through the city’s best donut shops. Fast forward to 2025 and his modest side hustle has grown into a full-time operation with 33 routes across 25 cities and counting.

“I’m super passionate about donuts, and I wanted to share that passion with others,” says Woelker. “I never could have guessed that it would lead me on this adventure, and I’m so thankful I get to do this.”

One of the latest additions to that adventure is Vancouver.

Finding a Home on the West Coast

For Woelker, choosing to expand to the West Coast city was easy. “It was a total no-brainer,” he says. “My wife and I have always loved the city. The people are fantastic, the food is incredible, and it’s just one of the most gorgeous cities in the world.” He was also struck by the city’s unique setting. “The fact that you can be standing downtown and see the mountains, the ocean, and skyscrapers all at once, it’s incredible.”

Of course, great scenery only goes so far when your business is built around baked goods. “I need to love the city, and I need it to have a great donut scene,” he adds. “Vancouver has both.”

Before launching in any new city, the team does their homework. “We do a ton of research,” Woelker explains. “We look at the Top 10 donut shops, we read online reviews, check social media, Yelp, TripAdvisor, the whole deal. We really build a picture of the donut scene.”

Made in Gastown

The Vancouver tour quickly found its home in Gastown, a neighborhood rich in both history and pastries. One notable get was Lee’s Donuts. “They came up time and again in our research, but they were only on Granville Island at the time, so we couldn’t include them,” he says. “We wanted them for years, and finally they opened a Gastown location, so we were able to add them to the tour.”

Other local stops include places like Breka Bakery, which many don’t even realize serves donuts. “We’re always on the lookout for those hidden gems,” says Woelker. “The places that make people say, ‘I had no idea this was here.’ In Breka’s case, people know about it but I wouldn’t say donuts are what it’s known for primarily.”

But as Woelker is quick to point out, the tour is about more than just donuts. “People are often surprised that we cover more than pastries,” he says. “It’s also a walking tour, a city tour, a bit of a history tour. Our guides are locals who know the city and love sharing it.”

That local expertise is a key ingredient. “Getting to play tourist in your own city is a lot of fun,” he says. “Our guides point out the hip coffee shops, the new restaurants, the places people might have walked past a hundred times and never noticed.”

Next Step – Global Domination

The Underground Donut Tour’s expansion shows no signs of slowing. Woelker is actively exploring new markets. “We just opened in Savannah and Detroit,” he says. “Detroit’s an interesting one for me personally, I’m from there originally, and when I left 20 years ago, there just wasn’t a lot happening. Now it’s thriving.”

In Canada, he’s eyeing cities like Calgary, Montreal, and Ottawa. “We’re always looking for cities that are growing as tourist destinations and have a strong food scene,” he says. “That’s the sweet spot for us.”

A Love for the Classics

As for trends in the donut world, Woelker sees two camps: classic and creative. “There are shops focused on doing simple, high-quality donuts at a great price, and there are others going all out with presentation and wild flavours,” he says. “Donutelier in London is a great example—those donuts are like works of art. Dominique Ansel in New York is another, with his ‘Cronut’ and other innovations.”

When asked about his personal favourite, he doesn’t hesitate. “At the risk of sounding boring, I love a traditional old-fashioned donut,” he says. “Parallel 49 and Lucky’s Donuts in Vancouver both do incredible versions. You can watch them being made in real time, and you can taste the difference. That freshness really matters.”

Ten years in, Woelker still sounds like someone who just really loves donuts. “It’s still fun,” he says. “It still feels special to share something I love with people in cities I love.”

Vancouver, it seems, is a perfect fit.