20 Outdoor Adventures to Knock Off Your Chicago Bucket List in 2016

The Shawnee National Forest in southern Illinois is a must-see destination for outdoor enthusiasts. - Michael

Chicago will never be mistaken for a mountain town. Our beaches aren’t really an option for much of the year, and the weather can at times be, let’s say, challenging. But those poor excuses shouldn’t stop anyone from enjoying the truly great outdoor experiences available in the area. In fact, as we ring in 2016, it’s time to think about how to get more outdoor time in the coming year. With that in mind, we offer these 20 outdoor adventures to knock off your Chicago bucket list. Let’s not hear any excuses this year.

1. View the Waterfalls at Starved Rock State Park

Come to Starved Rock State Park in the spring to see the waterfalls at their best. John

Starved Rock State Park is the go-to place for outdoor adventure in central and northern Illinois, attracting more than 2 million visitors a year. While Illinois has a deserved reputation for its flatness, Starved Rock features 18 canyons that were formed by melting glaciers. All year, you’ll find impressive rock formations, wooded hiking trails, and scenic lookouts atop sandstone bluffs that, quite frankly, make you wonder how this all got to central Illinois. But in the spring and after a good rain, the canyons’ waterfalls are running, which is something to see. At just two hours from Chicago, the park is perfect for a day trip, but camping is available for those who want to stay longer and explore more.

2. Mountain Bike at Palos

The peerless Palos Trail System. Mark Montri

Almost everyone in Chicago has a mountain bike to ride on the Lakefront Path or other crushed-limestone trails in the forest preserves. But how many people take the time to find some real off-road trails? Make this the year that you discover the Palos Trail System, or go there more often. The forest preserve cluster southwest of the city has some seriously good singletrack and plenty of off-road riding for all abilities. You won’t be disappointed.

3. Enter a Paddling Race

Yes, paddling can be a relaxing experience to celebrate nature. Or it can be an aerobic exercise that rewards your skill and endurance. The Chicago area actually has two major paddling races, which can be done at breakneck speed or simply to enjoy the spectacle. The Des Plaines River Canoe Marathon in May and the Mid-America Canoe and Kayak Race on the Fox River in June are both historic events that should appeal to anyone who enjoys canoeing or kayaking.

4. Climb a Building

The Hustle Up the Hancock lets participants climb up 94 floors to the top of the Hancock Building. Sean Davis

OK, most of these may not technically be outside, but when you’ve got urban resources, why not take advantage of them? The city features several events that allow you to climb some of the tallest buildings in the world. The Hustle Up the Hancock is the biggest in February, with more than 4,000 athletes taking on the 94- or 52-floor climb. You’ll also find climbs up the Willis Tower, the Aon Center, and the Presidential Towers. Don’t want to stay inside? Try the Skyline Plunge, where you’ll be able to rappel down 27 stories outside theWit Hotel to raise money for the Respiratory Health Association.

5. Run a Marathon

The Bank of America Chicago Marathon brings more than 40,000 runners to the streets of Chicago each October. Bank of America Chicago Marathon

Sure, this is on a lot of people’s bucket list. But when you have one of the best marathons in the world, why not take advantage of it? The Bank of America Chicago Marathon brings more than 40,000 runners to the streets of Chicago each October. It’s become so popular that a lottery system is in place to get an entry, with deadlines for that coming early in the year. If you get closed out of Chicago, the Fox Valley Marathon is a good alternative in September.

6. Paddle the Skokie Lagoons

The Skokie Lagoons are an excellent spot for paddling. Brad Hagan

The Skokie Lagoons are an underused resource for paddlers in the area. In the 1930s, the Civilian Conservation Corps brought area flooding under control by creating the lagoons that you see today. Workers moved more than 4 million yards of earth, in what the Forest Preserve of Cook County says was the largest CCC project in the nation. Now you can enjoy their work in Winnetka, Northfield and Glencoe, with seven numbered lagoons of various sizes plus dozens of channels and islands that link them all together. You’ll spot plenty of wildlife and enjoy some isolation on the North Shore. Not into paddling? The North Branch Trail allows runners and cyclists to get a view of the lagoons. 

7. Camp at a Cook County Forest Preserve

Bullfrog Lake is one of the sites in the Cook County Forest Preserve system that offers camping. Emilie

Cook County’s Forest Preserves have traditionally provided the only real green space in the immediate Chicago area. For hikers, mountain bikers, and trail runners—not to mention picnickers, frisbee-throwers, and sunbathers—the forest preserves offer a wooded escape from the urban landscape of the city. But there was one thing all the diverse preserves had in common: You had to leave at sunset.

But that’s no longer the case—at least in five preserves that started permitting overnight camping last summer. It’s a big change for the Cook County Forest Preserve, which has spent the last several years creating and implementing a master plan to build new campgrounds and improve existing ones that in the past had only been available to established groups like the Boy Scouts. Take advantage of the opportunities close to home, particularly at Camp Bullfrog Lake, with its excellent access to mountain biking.

8. Bike Lake Shore Drive

Bike the Drive allows cyclists to take over Lake Shore Drive each year. JohnPickenPhoto

One of the most famous streets in the country shuts down the Sunday morning before Memorial Day each year for Bike the Drive, a ride that attracts thousands of cyclists for an incredible car-free view of the city. The ride is a fundraiser for the Active Transportation Alliance, which works to improve cyclists’ lives year-round. Win-win.

9. Paddle the Chicago River

Paddling on the Chicago River is a special treat on St. Patrick’s Day. Scott L.

One of the best views of the city is from down below. Yes, there was a time not too long ago when the Chicago River had a level of pollution that would make you think twice about getting close to the water. But with the help of organizations like Friends of the Chicago River, the river has become much cleaner and an enjoyable spot for recreation. And a popular one—several outfitters now take groups out in canoes and kayaks to explore downtown Chicago. You can get a ride from Urban Kayaks, Water Riders, Kayak Chicago and Chicago River Canoe and Kayak.

10. Explore the Kettle Moraine State Forest

Pine-lined cross-country ski trails are one of the reasons the Kettle Moraine State Forest is one of the best destinations for Chicago cross-country skiers. Wisconsin Department of Natural Resources

For both mountain bikers and cross-country skiers, the Kettle Moraine State Forest is not to be missed. The state forest contains more than 22,000 acres in southern Wisconsin, about 37 miles southeast of Milwaukee. Of course, you can hike, camp, fish, and do all kinds of outdoor activities, but the real draw are the more than 130 miles of trails to explore. It offers the best singletrack for mountain bikers within a reasonable distance of Chicago (about two hours) and groomed, pine-lined cross-country ski trails that will make you a quick convert to the sport.

11. Complete a Triathlon

The bike leg of the Transamerica Chicago Triathlon. TransAmerica Chicago Triathlon

For more than 30 years, the Chicago Triathlon has been one of the largest multisport races in the world. Participants swim about a mile in Lake Michigan, ride about 25 miles on Lake Shore Drive and run about 6 miles on the Lakefront Path (the sprint version of the race covers half those distances). It’s a great way to see the city and put your training to the test. What even more of a challenge? Ironman Wisconsin brings some of the best athletes in the world to Madison each year to conquer the 2.4-mile swim, 112-mile bike, and 26.2 mile run.

12. Explore the Shawnee National Forest

Garden of the Gods is just one of the incredible spots found in the Shawnee National Forest. Michael

Taking up much of the southern tip of southern Illinois between the Ohio and Mississippi rivers, the Shawnee National Forest contains more than 280,000 acres and some of the most scenic views in the state. You’ll find a wide variety of terrain, including rock formations at the Little Grand Canyon and the Garden of the Gods that look more like something you’d find out west than in the Prairie State. It’s a 300-mile trip from Chicago, but one well worth the vacation time for the incredible hiking, climbing, and camping.

13. Try Cross-Country Skiing

The start of the Illinois Northern Nordic race held at the Arrowhead Golf Course. Jeff Banowetz

Minnesota and Wisconsin have much more established cross-country ski communities, thanks partly to their heritage but also due to their better snow cover. But Chicago offers several excellent options, particularly for those who are new to the sport. Arrowhead Golf Course in Wheaton is an excellent place to explore, with both groomed trails and access to the Herrick Lake Forest Preserve with hilly, tree-lined trails. Camp Sagawau features lessons and very beginner-friendly terrain in the southwest suburbs.

14. Run the Length of the Lakefront Path

The Lakefront Path offers stunning views of the skyline. Chris Palmer

Chicago’s Lakefront Path is the city’s 18.5 mile jewel that allows runners and cyclists easy access to traffic-free movement across the city’s front yard, with views that can’t be beat. It’s worth exploring the entire length of the trail to discover all it has to offer. If you’d like some support on the run, the Chicago Area Runner’s Association’s annual Ready to Run each September is a point-to-point run (not a race) that covers the entire route.

15. Get Muddy

The Spartan Race features tough obstacles and plenty of mud. Deveion Acker

If you haven’t discovered obstacle racing yet, make this the year to give it a try. The Warrior Dash, which has hundreds of events around the world, is actually headquartered in Chicago, and its annual event on a private farm in Channahon, Illinois, brings more than 20,000 people out for the mud, crazy obstacles, and post-race party. Other popular races in the Chicago area include the Spartan Race and the Tough Mudder.

16. Go Whitewater Rafting

Whitewater rafting on the Menominee River. david.dames

It may not be as well known as in other parts of the country, but there is indeed whitewater rafting within driving distance of Chicago. The closest destination is just a two-hour ride from Chicago on the Vermillion River near Starved Rock State Park. Or make the trip to northern Wisconsin and make a weekend out of it on rivers that offer Class III and IV rapids in the spring.

17. Ride a Century

Door County, Wisconsin, is a popular spot for road riding all year. It hosts the Door County Century in the fall. bradleypjohnson

The century ride—100 miles—is the goal of many road cyclists. It’s an impressive accomplishment yet an achievable goal as long as you put in the training. Most are held in the second half of the year, giving you time to get that training in. The North Shore Century is one of the best, taking riders from Evanston to Wisconsin and back each September. While the Door County Century is a popular ride for a weekend trip.

18. Climb the Hills in Galena

Historic Galena is a great place to stay and enjoy the hilly terrain. Ethan Olson

Illinois has a well-deserved reputation for flatness. But the old mining town of Galena, Illinois, offers visitors a completely different part of the state. The town has become a tourist destination, filled with bed-and-breakfasts and antique shops, but it’s also a great place to take the road bike for some honest-to-goodness hills. The Galena Lead Rush Half Marathon in the fall puts runners to the test, while Fever River Outfitters offers rentals and organized trips for cyclists and paddlers.

19. Rock Climb at Devil’s Lake

Devil’s Lake is one of the top climbing spots in the Midwest. anjanettew

Devil’s Lake is the most visited state park in Wisconsin, offering magnificent panoramic views of the 360-acre Devil’s Lake from 500-foot high quartzite bluffs. For rock climbers, Devil’s Lake is one of the top destinations in the Midwest. With 100-foot tall cliffs, the park offers terrain difficult to find anywhere else this far from the Rockies. More than 2,000 climbing routes of all skill levels are available in the park. Located in the south central part of the state, the park is a manageable drive from Chicago and not far from the state capital in Madison.

20. Boat on Lake Michigan

Chicago and the suburbs have several beaches that are great to launch a sea kayak. joenevill

Yes, it took us to the last item on the list to hit Chicago’s most impressive feature. It probably shows that we take Lake Michigan for granted. Don’t. Of course, you can take a sea kayak out on the lake, and Kayak Chicago offers 2.5-hour lake paddles that start at North Avenue Beach, just north of downtown Chicago. The city of Evanston rents kayaks and stand-up paddle boards by the hour at the Dempster Street Beach. Group kayaking classes are also available for beginners. Great Lakes Kayak, a kayak retailer in Lake Bluff, Ill., offers lessons, while The Northwest Passage in Wilmette, Ill., offers private and semi-private lessons for a variety of kayaking disciplines. Chicago SUP offers rentals, lessons and even yoga classes on stand-up paddleboards from North Avenue Beach downtown.

Originally written by RootsRated

Featured image provided by Michael

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