A brand new DC startup desires that will help you get outdoors. Meet City Open air


When Urban outdoors founder Kay Rodriguez When she moved to Chicago in 2019 after a brief stint on international adventures, she was keen to explore the city’s outdoor recreation scene.

But interviewing several locals yielded no information about the city’s trails, hikes, or related activities. So she did her own research and eventually created one WordPress Page of guides to their favorite hikes in the Windy City.

“Within three months I had a handful of guides for the Chicago area and we were having about 15,000 visitors to the site each month,” Rodriguez said Technically. “I said, ‘Oh my God — well, if Chicago wants that information, I would guess that everyone, everywhere, wants it.'”

Rodriguez, who has a background in management consulting and corporate strategy in technology and media, quickly expanded the blog to DC and Houston, Texas, where she previously lived. Urban Outdoors continued to grow when the COVID-19 pandemic hit in March 2020, forcing her to quit her job and work full-time for the company.

A few years later, Rodriguez has transformed the business that moved her to DC into a thriving website with 150,000 to 200,000 monthly visitors and 27,000 email subscribers. Many of these readers began asking about groups to join and other resources to not only get out there, but to find others to go with them. This led to her work externallya forthcoming web and mobile app designed to foster connections between outdoor enthusiasts.

“People really, really want to talk about it and they’re really passionate about it, and they have issues and pain points and things that they would like to see changed in their cities and in their own personal lives,” Rodriguez said. “But the resources are so low that they have not been able to do that.”

Outerly is currently in beta mode, and Rodriguez is hoping to launch the web app in the next month or two before debuting the mobile app soon after. The web app is currently based on a WordPress Stack with a customized frontend. Eventually, she hopes to help develop a common database for the web and mobile app Respond natively for each of the frontends.

Outerly allows users to search for information about local trails based on reviews from people they’ve already hiked. You can filter by difficulty, length, time, and distance from DC, as well as search for upcoming events associated with individual trails. There will also be a premium feature that will allow users to request participation in an activity on a specific date – and find others to go with them. Alternatively, when searching for a trail, they can see if any of their friends who use Outerly have marked it as interested and plan an activity together.

Urban Outdoors (which Rodriguez plans to separate from Outerly after its launch) recently won the Early Stage category DC Startup Week pitch competition and received a $65,000 SAFE investment. It hopes to open a $2 million seed round in the coming months to help launch and scale the app, building full-stack versions of the web and mobile platforms and the will include entering new target markets where Urban Outdoors already has a large audience.

“People are always looking for friends. They are always looking for things to do and as a result there are always things they are making [DC] such an exciting place to live and be,” said Rodriguez. “What drew us to DC, and what we think DC can capitalize on from us, is that people in DC want to meet other people and also want to know where they can get out.”