Outside routine: KCK native’s Urban Hikes reveal unseen Kansas City hidden in plain sight
March 9, 2021 | Austin Barnes
Traditional paths aren’t for Lisa Peña — and her latest business venture (or adventure) is proof, aiming to show Kansas Citians on both sides of the state line an unfiltered version of two cities they might think they already know.
“It really perpetuates getting to know your city more,” Peña, founder of Urban Hikes KC, said of her experiential small business, which takes participants on 4- to 5-mile guided tours of the twin Kansas Cities, immersing them in their respective histories and community cultures along the way.
“They’ll explore places they’ve never seen before.”
From Strawberry Hill to the back-alley ways of the Crossroads Arts District, Peña’s poured her knack for finding adventure into every hike the company offers, allowing her local upbringing and passion for finding adventure in her own backyard to guide the experience every step of the urban way.
“We start out places that you would for sure know, like the Liberty Memorial. And then we go down to Union Station. But I always point out the details that most Kansas Citians don’t always pay attention to,” Peña said of her six unique hikes, which start out at $32 per person and celebrate everything from street art produced during SpraySeeMO to local food and historic architecture.
Urban Hikes KC
Elevator pitch: This hike is full of Instagramable spots and hidden Kansas City gems. You can join a hiking tour with others, become a founding member of our Urban Hiking KC Club or set up your own private tour with a minimum of three. This won’t be a leisurely stroll in flip flops; you’ll need good walking or running shoes and your water bottle!
“[On our Westside Neighborhood hike] often we’ll stop at [Paleterias] Tropicana and get some ice cream if the group is interested. And then there’s some hidden steps just north of the Guadalupe Centers. … They’re these really secluded steps that we take to get all the way to the top near Observation Park. We feel like we’re on top of the city and have this awesome view and I’ll talk about the history of the West Side.”
Raised in Rosedale — her thrill-seeking forged in exploration of the woods near her childhood home — the chance to understand and embrace the history of pockets of Kansas City she often wondered about as a kid offers Peña just as much excitement as it does her crews of hikers, she said.
“Downtown Kansas City wasn’t a thing at all growing up, but Westport was,” she said of her perception of life on the Missouri side of the state line in the early 2000s, when places like the now-bustling River Market area felt forgotten.
“I remember being a teen and going to the vintage shops and restaurants [in Westport] and loving that feel. That’s when I really started to appreciate cities and would look for cool spots. … I have always really liked being outdoors. I also really like fitness and I love being around people.”
Click here to learn more about Urban Hikes KC and its tour offerings or to book a hike.
Peña’s decision to take her love for the cities a step further came while listening to a podcast, “Side Hustle Nation,” she recalled.
“That podcast highlighted a woman named Alex Kenin who has an urban hiking business in San Francisco. She talked about her business and when I heard her [story] I was like, ‘Wow, this is something I would love to do and would love to make happen in Kansas City.’”
An email and a phone call later, Peña received Kenin’s blessing to try something similar in the metro, adding to her resume of side hustles, which also includes making sauerkraut and kombucha, teaching others how to do the same, leading Spanish classes for kids, and working as a Spanish-English interpreter for local medical services.

Urban Hikes KC; mural credit Global Prairie
Peña found additional entrepreneurial inspiration on the job, working for five years with Girl Scouts of Northeast Kansas and Northwest Missouri — an organization she didn’t have the opportunity to participate in growing up, but fully embraced as an adult.
“Maybe 5 percent of girls in Wyandotte County are Girl Scouts — but in Johnson County [around] 30 percent are Girl Scouts,” she said of market share within the program, which she worked to expand, primarily in Hispanic communities across the region.
“We were always talking about empowering girls to be entrepreneurs — especially with the cookie sales. Everything behind the cookie sales is [about] entrepreneurship and there are all these badges of entrepreneurship and I really feel like that culture and community at Girl Scouts helped me to feel like I could do it too,” Peña said.
“If we’re working so hard for girls to feel like they can do it, I was like, ‘As an adult, why can’t I do it?’ It gave me the courage to actually go out and try my idea.”
And even in light of a global pandemic, Peña’s had no regrets in following her gut and going all-in on her dream business.
“Urban hikes are an amazing way to get out of your routine, to get outside, and to spend time with someone else,” she said of why locals should take advantage of her tour offerings, which now include corporate outings as employers begin to bring teams back together in offices around both cities.
“I feel like there’s so much to see and I’m just like, ‘Wow, this is so cool,’ I want to share it with others.”
Click here to follow Urban Hikes KC on Instagram or here to connect with the tourism startup on Facebook.
This story is possible thanks to support from the Ewing Marion Kauffman Foundation, a private, nonpartisan foundation that works together with communities in education and entrepreneurship to create uncommon solutions and empower people to shape their futures and be successful.
For more information, visit www.kauffman.org and connect at www.twitter.com/kauffmanfdn and www.facebook.com/kauffmanfdn
Featured Business

2021 Startups to Watch
stats here
Related Posts on Startland News
Social reaction: Kansas City discusses whether it’s ‘too nice’
Is Kansas City too nice? That question recently provoked a lively discussion amongst the Kansas City entrepreneurial community, eliciting thoughtful responses on the merits and disadvantages of the area’s candor. Startland News compiled some of those comments below that we found on our website in what will mark a new focus that aims to stimulate…
Kansas City to play tech teacher again with gigabit conference
Kansas City’s years of experience with gigabit will once again allow it to play Internet instructor. Thanks to popular demand, non-profit organization KC Digital Drive announced that it will host the second-annual Gigabit City Summit May 16 – 18. The summit will welcome dozens of cities to learn from Kansas City’s experience with gigabit Internet…
Regional Roundup: VC valuations, bootstrapping
Welcome to our new series called Regional Roundup. Every couple weeks we’ll pull together compelling articles, podcasts, videos and more related to startups and innovation in the region. Let us know what you think, and send us any ideas or content that you’d like to share. Sit back and read (or listen or watch) some…
Events Preview: TEDxUMKC
There are a boatload of entrepreneurial events hosted in Kansas City on a weekly basis. Whether you’re an entrepreneur, investor, supporter or curious Kansas Citian, we’d recommend these upcoming events for you. WEEKLY EVENT PREVIEW KC Roundtable Annual Holiday Party When: December 3 @ 5:30 pm – 8:00 pm Where: The Well Come celebrate the end of…





