The Chicago Explore More Guide

10 Outdoor Adventures in and Around Chicago

Here we outline our favorite ways to enjoy the outdoors in and around Chicago. Our partner, The North Face, is helping us bring this guide to life with The Chicago Explore More Challenge, which starts September 26, 2019 and runs through August 24, 2020.

Read on to find out how you can win prizes, find new adventure buddies, and most importantly, get outside.


The Explore More Challenge

The Explore More Challenge, presented by The North Face, is a multi-month challenge that rewards you for going outside with new Mappy Hour friends. Each participating chapter will launch a guide with 10 challenges (see below) that can range from exploring your city to finding further afield outdoor gems in your state. Each adventure, which will be selected by your chapter leaders, will hold a point value. Mappy Hour members will compete to complete the challenges (aka go outside!). The North Face is further supporting this new program with prizes for all chapter members who complete the challenge and an even bigger prize for the first person to complete it in each chapter!

The Rules: Chicago Explore More Challenge


  • Our challenge dates run from September 26, 2019 to August 24, 2020. You can complete adventures any time between those dates.
  • Reach 60 points to complete The Explore More Challenge. Your reward: a prize from The North Face. Bonus prize if you complete all the adventures on the list. And the first person to reach 60 points will take home The North Face grand prize.
  • Complete each of the Explore More adventures as many times as you’d like, however, you must explore a new location to earn points a second time. (ex: Adventure 7: +5 points for visiting Matthiessen State Park. +5 more for visiting Illinois Beach State Park)
  • We’ll have a logbook at every Mappy Hour event at The North Face, with locations in Wicker Park and on Michigan Avenue, this year. You just have to come to Mappy Hour to “sign in”. Bring a picture of yourself doing the challenge and your chapter leaders will sign off in the logbook.
  • We know that sometimes you miss a Mappy Hour – no worries, you can do an adventure in October and then sign in the following March.

Our list features a variety of outdoorsy adventures – from biking to climbing to camping within city limits – and are all adaptable no matter your experience level.

Adventure 1: Climb in Chicago

Rock Climbing in Chicago
The Challenge: Climb in Chicago (5 Points).

Sure, it’s a spectacular view from the top of the Sears Tower. But how about reaching new heights by climbing some of Chicago’s tallest rock walls and bouldering areas around the city. If you’re looking to climb indoors, check out First Ascent or Brooklyn Boulders, or head downtown to the Maggie Daley Park to climb in the heart of the city. For a more unique climbing experience, check out some of Chicago’s hidden climbing gems, like the old ore walls at Steelworkers Park or The North Face’s new boulder area in Palmisano Park on Chicago’s Southwest Side.

The Challenge:

Climb on a wall of your choice within city limits. (5 points)

Pro Tip: Various meetups host group climbs throughout the week, including Sending in Color (a group dedicated to diversifying the outdoors) and First Ascent’s #WomenCrushWednesday.

Adventure 2: Paddle the Chicago River

Paddling on the Chicago River
Paddle the Chicago River (10 points).

Drifting through the city on the Chicago River is one of the most beautiful ways to see Chi-town. For one, you get to view the towering skyscrapers and the city’s architecture without elbowing your way through crowds. And second, you have the chance to paddle beyond downtown (like the North Branch of the Chicago River) to get an up-close-look at wildlife and green space that sits on the outskirts. This list is a great place to start if you are new to the Chicago paddling scene.

The Challenge:

Paddle the Chicago River on a kayak, canoe or SUP. (10 points)

Pro Tip: We recommend renting from Chicago River Canoe and Kayak if you want to paddle the more remote/natural North Branch and Kayak Chicago if you want city views.

Adventure 3: Explore the Chicago Forest Preserves

Runner in the Chicago Forest Preserves
Explore the Chicago Forest Preserves (5 points).

The Forest Preserves of Cook County (FPCC) give outdoorsy Chicagoans access to 70,000 acres, more than 200 miles of paved trails, and more than 100 miles of unpaved trails. There are 24 dedicated Illinois Nature Preserves in total, and each offer a different flavor of outdoor adventure and native wildlife. Take a bike ride through La Baugh Woods on the The North Branch Trail System which offers ~20 miles of paved and unpaved routes. Or hike (or mountain bike) in the hilliest section of the city on the Palos Trail System that winds through rolling hills and deep ravines. Don’t forget to hit the trails in winter – you’ll love the solitude.

The Challenge:

Hike, bike, snowshoe (or choose your own adventure) in the Chicago Forest Preserves. (5 points)

Pro Tip: Check out the FPCC interactive map online which helps you find trails, research the preserves, and keep track of where you are while you hike/bike/etc.

Adventure 4: Take Public Transit to the Trailhead

Hiking near Chicago
Hang out at a Local Nature Center (5 points).

Many Chicago-area day hikes are accessible by train. In fact, Mappy Hour CHI Chapter Leader Erica wrote a whole story in the Chicago Tribune about how to do it. Whether you’re taking the Blue Line west out to the Cumberland stop to reach the Des Plaines River Trail, or hopping on the Metra Union Pacific North line to The Openlands Lakeshore Preserve, trains are a sustainable way reach the trailhead.

The Challenge:

Use Chicago’s public transportation to get to the trail (The “L”, Metra, Divvy). (5 points)

Pro Tip: If you’re hiking on the weekend, make sure to check out the Metra train schedules which have less-frequent trains running on the weekends.

Adventure 5: Camp in the City

Camp near Chicago
Camp in the city (15 points).

Believe it or not, there are a number of campgrounds right in Chicago’s backyard. The Forest Preserves of Cook County have 5 dedicated campgrounds located throughout the preserves. All campsites can be reserved in advance and a handful of the campgrounds even offer cabins with creature-comfort amenities.

If you’re feeling really adventurous, take on Chicago’s first and only backpacking route: The Outerbelt. Curious what it’s like to backpack here? Check out The Outerbelt map or read about the inaugural adventure.

The Challenge:

Pitch your tent at a Forest Preserve campground for a night or two. (15 points)

Pro Tip: You can rent out camping gear from the preserves if you don’t have your own (or need a few extras).

Pro Tip #2: You don’t want to miss this amazing Beer in the Woods event (going on its 3rd year)!

Adventure 6: Bike to the Chicago Botanic Gardens

Biking in Chicago
Bike to the Chicago Botanic Gardens (10 points).

You can’t go wrong with a trip to The Chicago Botanic Garden – its 27 spectacular gardens and 385 acres is well-worth the trip north of the city. But a little-known secret is that you don’t have to pay expensive parking fees if you bike there. To get to the gardens by bike, take the North Branch Trail (20 miles) or use the one-mile link between the North Branch Trail and take the Green Bay Trail (which runs closer to Lake Michigan) instead. Maps here if you’re already curious how to plan your route.

PS: For more bike adventures, check out this top bike trails list and Chicago’s ‘Mellow Bike Map’ for low-stress routes.

The Challenge:

Swap your car for a bike and ride to the Chicago Botanic Garden. (10 points)

Pro Tip: If you’re planning on riding a Divvy bike, leave early. You don’t want to get stuck without a spot to dock at the front gate.

Adventure 7: Check out an Illinois State Park

Swimming at Illinois State Park
Check out an Illinois State Park (5 points).

Have your pick of 70 state parks in Illinois. Our favorites? Dang, that’s a hard question. We’d recommend Matthiessen State Park and Starved Rock State Park (they’re next door neighbors). They’re a must-see if you’re a Chicagoan. Illinois Beach State Park is another favorite because it’s close to Lake Michigan and has 5 miles of trail (and a shorter yet gorgeous 2.2-mile loop). Check out all your options on the DNR website which lists state parks by region.

The Challenge:

Explore one (or several) of Illinois’ stunning State Parks. (5 points)

Pro Tip: If you decide to explore Starved Rock State Park, start on the east side of the park and make your way back to the front entrance. You’ll miss crowds (and explore some lesser-seen canyons).

Adventure 8: Visit the Indiana Dunes National Park

Visit the Indiana Dunes National Park (10 points). +10 points if you take The South Shore Line to get there.

The Midwest welcomed its newest National Park – The Indiana Dunes National Park – in 2019.  The Indiana Dunes spans 15,000-acres in northwest Indiana along the southern shores of Lake Michigan. And you can even conveniently access it by taking the South Shore Line. Not sure if it’s worth the trip? Check out this article by The New York Times, whose writer trekked out to the dunes for a weekend camping trip.

The Challenge:

Check out the Indiana Dunes, the 61st National Park in the US. (10 points, +10 bonus points if you take public transit)

BONUS: Earn an extra 10 points if you take the South Shore Line (public transit) to get there.

Adventure 9: Hang out at a Local Nature Center

Nature Center in Chicago
Hang out at a local Nature Center (5 points).

Nature centers are great because you can add a layer of continued education to your outdoor adventure. They’re the perfect place to learn about native plant and animal species, give back to the community. Some of our favorites include the North Park Village Nature Center, the Little Red Schoolhouse Nature Center, and Peggy Notebaert Nature Center in Lincoln Park.

The Challenge:

Visit a local nature center to learn a bit more about native Illinois. (5 points)

Pro Tip: Chicago’s nature centers host a variety of fun, family-friendly events. Check out North Park Village’s event page to get a taste.

Adventure 10: Clean up While You Explore

Clean up at a local park/beach with your 11th Essential – a trash bag that you add to your essential items list. By bringing a bag with you on the trail, you can make stewardship a priority on every adventure. While packing a plastic bag to pick up trash on the trail is a great place to start, you can also volunteer with local organizations like the Alliance for the Great Lakes for local beach cleanups.

BONUS: Earn an extra 1 point for every full plastic grocery bag of trash you collect.

The Challenge:

Collect trash on the trail, in the park, or on the water. (10 points, +1 bonus point for every grocery bag of trash you fill)

BONUS: Volunteer for an Outdoor Non-Profit

Get an extra point for each hour that you spend time volunteering with a local non-profit that advocates for the improvement, protection and recognition of Chicago’s green spaces and public places. The Chicagoland Environmental Network is a good resource to find groups to support.

Plus, here’s a short list to get you started:

Points: The Chicago Explore More Challenge

Completed at 60 Points

Adventure Points
Climb in Chicago 5
Paddle the Chicago River 10
Explore the Chicago Forest Preserves 5
Take Public Transit to the Trailhead 10
Camp in the City 15 
Bike to the Chicago Botanic Gardens 10
Check out an Illinois State Park 5
Visit the Indiana Dunes National Park+10 points if you take The South Shore Line to get there 10, 10 point bonus
Hang out at a Local Nature Center 5
Clean up While You Explore+1 point for every full plastic grocery bag of trash you collect 10, 1 point bonus
BONUS: +1 extra point every time you adventure with a new Mappy Hour friend. 1
BONUS: +1 extra point for every hour you volunteer with a local, outdoor-focused non-profit. 1 (up to 10 points)


Photo credits:

Forest Preserves of Cook County

About the Challenge

The Explore More Challenge is a multi-month challenge that rewards you for going outside with new Mappy Hour friends. Each chapter guide includes 10 challenges that can range from exploring your city to finding further afield outdoor gems in your state. Are you ready to explore more?

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