Take An Urban Adventure—And Bring This Gear

I discovered urban adventure when I changed my perspective on what “adventure” really means. Getting outdoors doesn’t always look like climbing thousands of vertical feet up a mountain or taking on grueling trails that push you to the limits. Instead, it can look like escaping in whatever way speaks to you—on an adventure anywhere you want to roam. 

For me, that’s seeing my city, Chicago, not just as a concrete jungle of streets and skyscrapers, but a network of hidden forests and green sanctuaries waiting to be explored—all just minutes from my own front door. 

Truth is: Urban adventuring is a treasure hunt. Discover day hikes down dirt paths cutting between neighborhoods; Take a ride on a tucked-away trail in remote corners of the city; Navigate an unmapped nature sanctuary; Find the perfect picnic spot in a park that’s less-explored by other people. 

"It’s in the city where I feel like a real explorer, uncovering urban wilderness that others write off." 

You can unlock a portal to pockets of urban nature if you seek them out. In these urban-yet-wild spaces, the sounds of birdsong overtake the hum of traffic and crashing waves drown out the sounds of sirens. It’s the pursuit of discovering wild escapes, hidden trails, lush landscapes, and natural sanctuaries hidden in plain sight within a city. 

Of course, the greatest urban adventures come from the whispered directions of locals willing to share their secret spots that no tourist map would ever reveal. 

Here are my favorite nature hideaways in Chicago—and the best Osprey gear(Se abre en una nueva ventana) to bring on your next urban adventure. 

Daylite Tote Pack(Se abre en una nueva ventana) – Take a stroll in solitude at South Shore Nature Sanctuary.

Urban day hikes are ideal with the Daylite Tote(Se abre en una nueva ventana). This pack transitions seamlessly from tote to backpack, making it ideal for a trip to the farmer’s market to the coffee shop and to a hike on a wood chip trail. In Chicago, I grab my Daylite Tote for a hike at South Shore Nature Sanctuary(Se abre en una nueva ventana), a six-acre preserve and microcosm of native Chicagoland habitat: dune, beach, wetland, pond, woodland, prairie, savanna, and shrubland. After, I hit up my favorite farmer’s market in Logan Square(Se abre en una nueva ventana) followed by an iced coffee at New Wave(Se abre en una nueva ventana). 

Daylite Sling(Se abre en una nueva ventana) – Hop from train to trail in Wicker Park on The 606.

Ever heard of trail-to-town? Well, the Windy City has plenty of options for this kind of urban adventure. A must-try is The 606. This 2.7-mile-long trail—a former rail line—soars high above the Wicker Park neighborhood(Se abre en una nueva ventana) at roof level. It’s packed with trees, native plants, woodchip spur trails, and smooth pavement for walking, running, and biking. The commuter-friendly Daylite Sling(Se abre en una nueva ventana) makes the most sense for this adventure—no matter if you’re on bike, foot, or riding the train. The 5-liter sling pack is functional, breathable, and stylish and provides plenty of room for items you need for the city, adventuring, or both!

Tempest 6(Se abre en una nueva ventana) – Wander wild trails at Burnham Nature Sanctuary.

Burnham Nature Sanctuary(Se abre en una nueva ventana) on Chicago’s south side is full of wild surprises. The wildlife corridor includes paved pathways, boardwalks through prairie and woodland, and a 1-mile out and back wooded nature trail that will make you forget you’re steps from Chicago’s iconic Lakeshore Drive. The multi-sport Tempest 6(Se abre en una nueva ventana) is a solid choice for hiking (and biking, trail running, and more) on this section of off-the-beaten-path trail. In the dead of summer, you’ll be thankful for easy access to water. Dual-zippered hipbelt pockets, a dual-zipper panel, and massive interior pocket can also easily store essentials like snacks, sunscreen, and your phone. 

Escapist Wedge Bag(Se abre en una nueva ventana) – Bike to the best skyline look-out at La Ronda Parakata Gathering Space.

There are tons of great lookout points to soak in the view of Chicago’s skyline. But nothing beats the La Ronda Parakata Gathering Space(Se abre en una nueva ventana), in my humble opinion. You have to hike on the edge of Lake Michigan along winding woodchip path flanked by native tall grasses to get there, and it’s totally worth it. From the top of a hill under a hand-woven structure of vines, you get an epic view of the city looking north over Burnham Harbor. If you’re into biking like I am, then you can ride up to the lookout on the path too. Just keep an eye out for hikers, runners, and dog walkers on the way. Pack snacks (and bike tools) in the Escapist Wedge Bag(Se abre en una nueva ventana) for the journey. 

Still want more adventure? Hit up the nearby 119.7-acre Northerly Island Park(Se abre en una nueva ventana) for a bike ride or a hike on over 2 miles of paved and unpaved path at this stunning lakeside nature preserve. 

Transporter Gear Tote 60(Se abre en una nueva ventana) – Pack for a picnic at your favorite local park.

Urban adventures can be leisurely too. The Transporter Gear Tote 60(Se abre en una nueva ventana) is a haul-it-all bag that can fit food, chairs, a blanket, and so much more—making it ideal for a picnic at the park. Dual straps let you cinch gear down inside so nothing falls out and a central divider helps you organize items inside with ease. Whenever I’m headed to my favorite parks—Palmer Square Park(Se abre en una nueva ventana) in Logan Square or the Chicago Riverside River Park(Se abre en una nueva ventana) in Lincoln Square—for some lounging with friends, I always have my Transporter in tow.