This post was written by Kay Rodriguez, the founder of Urban Outdoors. Think of it as an annual “state of the union” update on the site and community. She gets extremely personal in this particular update, and some of the topics she discusses may trigger negative emotions.

On December 1, 2019, I officially launched Skyline Adventurer, which is the website that would eventually evolve into Urban Outdoors. Since then, we’ve grown to a team of 6, we’ve published 173 guides across more than 50 USA cities, and a whopping 390,678 individual people have visited our site – nearly 100,000 of them in November alone.

I rarely come onto the site to write in first person, but to celebrate a year since our inception, I wanted to give you all a glimpse at the story behind building Urban Outdoors during a global pandemic, and how it helped me through my own personal trauma in a time where my health nearly killed me. Additionally, I wanted to show you some of the amazing strides our community – yup, including YOU – has made this year.

Humble Beginnings

It was 2019, and I remember walking around the sidewalks of Lincoln Park, Chicago in the sweltering August heat, talking to a friend about this little idea I had to make the outdoors more accessible to city folks. I’d just moved to Chicago, and I was struggling with how inaccessible the outdoors – hiking in particular – felt as an urban dweller in the Midwest without a car.

I’d built several websites before, most recently Jetfarer, which was a blog dedicated to helping millennial professionals maximize their limited vacation time through travel. In the ever saturated travel industry, I found it extremely difficult to differentiate my website and business from the millions of other travel blogs out there.

In the beginning, I simply wanted a change of scenery from the travel industry. I wanted to find a “recession-proof” alternative to Jetfarer that I could work on even when people weren’t traveling. This August afternoon would be the first time I’d verbally articulate my desire to make the outdoors more accessible to the masses. In that moment, Urban Outdoors was born.

From the beginning, Urban Outdoors felt different. The outdoors was an industry that I’d spent a lot of time in personally, but very little time professionally. I wasn’t a champion climber, a speedy skier, or a super fit hiker…I was just a normal, outdoor-loving lady living in what seemed like the least outdoor-friendly city in the country.

I bought a domain name – – and built the website soon afterward. With that, our journey began.

Launch and Liftoff

At the time, I was still working full-time at a small startup in Chicago, so I spent what little free time I had working on getting the website ready to launch. I figured I’d pilot with two cities I knew well – Chicago and DC – to see if this idea actually had any traction. I also hired a student to help me with some writing and a social media assistant to help with promotion, using money that I was earning from Jetfarer.

Finally, on December 1, 2019, we launched the website publicly into the world, with just a handful of articles on kayaking, hiking, rock climbing, and biking in DC and Chicago. That month, we’d see 1,583 unique visitors to the site. Not huge, but definitely not negligible. By the end of 2019, we helped 1,583 people get outdoors across two cities, and I felt inspired that this idea could actually work.

Personal Turbulence

And then, something tragic happened. In late December 2019, the Chicago darkness and the loneliness of moving to a new city without many friends or supports hit me HARD. I found it difficult to focus on anything – my full time job, my websites, my hobbies. Even getting out of bed most days was extremely difficult, and I’d sometimes go days without eating anything or doing my normal daily activities.

Each day, I palpably felt the strain of not being able to go outdoors or do anything. Few people knew I was suffering the way that I was. Slowly, these feelings of dread and hopelessness began to consume my life, and just a few days before Christmas, I decided I didn’t want to be alive anymore.

I’ll spare you the specifics, but that day was a blur. Luckily, two people close to me had a feeling that something wasn’t right, and they found me in my apartment and rushed me to the emergency room. I spent nearly two weeks in the hospital, recovering from the severe depression that chewed me up and spit me out.

Following discharge, I’d go on to spend nearly two months in a recovery program to help me get on my feet again. I tried to go back to work full-time, but didn’t last more than a few weeks before I felt so crushed under the weight of everything that I couldn’t continue. Naturally, Urban Outdoors took a back seat during this time. I didn’t touch the site for weeks at a time.

The Pandemic Hits

In March, I finally started to feel like I was recovering, but news of the COVID-19 pandemic started to become more and more prevalent. Chicago was completely locked down, closing nearly every urban park and green space to the public. Even if I wanted to go outdoors now, I couldn’t, along with the millions of others in cities where lockdowns were happening.

Jetfarer took a massive hit to traffic and earnings, I could no longer work at my full-time job because of my mental health, and I felt myself spiraling back into a place of despair. I didn’t have much else to do but pour my energy, heart, and soul back into Urban Outdoors. My trusty writer sidekick, Natalie, and I bulldozed through tons of articles, researching outdoor activities and interviewing locals in cities around the United States to provide much-needed resources on the outdoors.

Despite our efforts, March and April saw little traffic growth because of the pandemic. Then, in May, as more research was released about the outdoors being a safe place to go during the pandemic, things started to change. People flocked to our guides to learn more about hikes and waterways in their local areas where they could practice safe, socially distant outdoor activities. We saw massive spikes from May onward – people all over the United States wanted to get outside, and we were their ready companion.

In the process of building and expanding the website, I personally began to go outside more and more. Not in Chicago, where most trails would remain off-limits until the mid-summer, but in the surrounding areas and parks that I’d never visited or considered before. I’d start with daily walks around my neighborhood, and then eventually took short road trips to hike in nearby state parks.

In the summer, I bought a used Mercedes Sprinter van and converted it into a camper, which I’ve been living in ever since.

Creating Urban Outdoors was the most impactful aspect of my own personal recovery. Without the outdoors, and the thousands of steps I’ve taken on trails this year, I don’t know where I’d be today. Moreover, watching this community grow from just a handful of people to hundreds of thousands of outdoor lovers each month has brought me an incredible sense of joy. It’s like I felt the world healing alongside me as we worked through the difficulties of 2020 together.

Building, growing, and living the mission of Urban Outdoors healed my mind and heart in ways that no medication, hospital program, or therapy ever could have. It gives me a reason wake up in the morning and a reason to smile as I fall asleep. This incredible community has benefitted me in more ways than I can ever articulate – to each and every one of you who went on this journey with me and Urban Outdoors: THANK YOU.

Today & Tomorrow

Our community has grown from 1,583 unique visitors in December 2019 to 98,187 unique visitors in November 2020. We’ve helped over 390,000 people across the United States and Canada get outside in the last year. And we’re definitely not stopping any time soon.

It takes a village, and we’ve seen time and time again that when we grow the number of voices on our platform, we can make the outdoors accessible to even more people. I couldn’t do what I do here at Urban Outdoors without our incredibly thoughtful, passionate writers:

  • Natalie Ringel, Paddling Writer & Our OG Content Manager (circa 2019!!)
  • Lindsey Novakowski, Snow Sports Writer
  • Garston Lam, Rock Climbing Writer
  • Rachael Hilderbrand, Tips & Gear Writer

Side note: We do still have some positions open – check out our Careers page for more information!

We’ve also got a LOT in store for 2021, including more of the guides you love and some fun new projects and products that we’re hoping to launch ASAP! You can sign up for our newsletter here to stay updated on the latest with Urban Outdoors – I promise you’ll want to be the first to hear about our newest developments.

One Last Note

I’ve spent a lot of time talking about myself and our team, but I wanted to give a huge shout out to you, our readers. We cannot do this without you – our business, growth, and livelihoods rely on you. Whether you used our site to get on the trails for the very first time or are an experienced hiker, climber, skier, etc. who wanted some new ideas, we’re so happy that you’ve chosen us as one of your trusted resources for information on the outdoors.

We’re also always open to feedback. We love hearing from you and learning about what you like or don’t like on our website. I am personally committed to listening and responding to each and every person who reaches out via our Contact page or email inbox. Come talk to us.

So, give yourself a hug and know that we’re so happy you’re here. We’ll see you outside!

With so much gratitude,

Kay Rodriguez, Founder of Urban Outdoors