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The Midwest is an unsung bastion of natural thrills and daunting romps that will keep you on your booted toes and may even knock you on your butt. Here, straight from the endorphin-chasing trekkers, bikers, climbers, paddlers, and thrill-seekers tearing up these parts, are 21 epic Midwest adventures for pushing your own boundaries.
Spelunking | Paddling | Biking | Climbing
Hiking
Indian Staircase
GROWING UP IN Batesville, all of our family vacations were camping and rock climbing. My parents would take us to Red River Gorge at least once a year. From the Sheltowee Trace Trail, there’s an unmarked path that veers into the woods, and then you run into a cliff with little holes in the rock, which are ancient footholds and handholds that the Native Americans left. You climb up to get to the top of the ridge. There aren’t trees or branches to hold. You’re literally on your hands and knees on these rocks. If you fall off, you’ll fall into the canyon. It has a higher probability of injury than any heights I’ve climbed in Indiana. It takes balance, overall strength, and confidence. But it’s exhilarating—you kind of ascend above the forest, and there’s an amazing view at the top—plus other trails to take you back down. You don’t have to descend backward. —Chelsea Cook, 32, brand manager at Eli Lilly & Co. and avid hiker
WHERE
Red River Gorge, Northern Kentucky
DISTANCE
3.1-mile loop
Adventure Hiking Trail
I’VE TAKEN SOME hikes that were much more along the lines of what you expect in the Appalachians than in Indiana. This trail is beautiful but challenging. The terrain is very much up and down, and there’s a limited number of places where you can get water. Most people have to go in advance and leave caches evenly spaced out at road crossings where they can be picked up as they hike. Put your name on it and the date you plan to pick it up. Most people along that trail recognize how important it is to leave it alone. The nice things about the trail are that it’s a loop, so you only need one vehicle, and there are cabins you can stay at along the Blue River. Keep an eye out for a salamander called a hellbender, which is about a foot long. They’re an endangered species. They’re perfectly harmless. The one I saw was just sunning itself on a log. —Walt Hoel, 58, retail sales lead at REI
WHERE
O’Bannon Woods State Park, Corydon, Indiana
DISTANCE
25 miles
Knobstone Trail
I ACTUALLY met my wife, Polly, on the Knobstone. We probably hike it 25 times a year. It’s the longest trail in Indiana; there’s nothing like it here. It’s steeper than a lot of the Appalachian Trail, and those elevation changes come quick. You might not see a lot of people, so it’s good if you like solitude. In winter, we’ll do a couple of end-to-end-to-ends in day-hike sections. It’s a great way to keep in shape for our backpacking trips out West. Some of its views are spectacular. With no leaves on the trees, you can see Louisville on a clear day. —Mick Parker, 66, retired executive and part-time buyer at JL Waters Adventure Outfitters
WHERE
Clark County, Indiana
DISTANCE
60 miles
Tecumseh Trail
YOU CAN FIND 4,498 feet of elevation gain and loss pretty easily in Brown County. The Tecumseh Trail is a good option. It’s a through-hike. I’d rather run it any day because then you don’t have to carry all the weight of a backpack. People will dump their water because they want to lighten their load. The best thing you can do to prepare is make sure you’re getting in mileage with the gear you would actually take with you. Good chocolate is also a must on a backpack trip. It’s a mood-booster. When people start getting low, bust out a chocolate bar and share some squares. It’s also a great tip if you’re hiking with kids. —Kate Nolan, 50, owner of Brown County Bikes and professional mountain bike instructor
WHERE
Morgan-Monroe State Forest, Martinsville to Brown County, Indiana
DISTANCE
42 miles
Three Dune Challenge
I HIKED EVERY trail in the state parks during COVID-19. The Indiana Dunes challenge is fun but really tough. The DNR challenges you to do the three tallest dunes consecutively, the equivalent of 55 stories. You’re in deep sand, and sometimes it’s really hot outside. The sand flies can be pretty bad. They’re all over you. I actually did it three times in a row on the same day. It’s not that tough if you’re in really good shape. —Terry Fletcher, 65, founder of the Indiana Trail Running Association
WHERE
Indiana Dunes State Park, Chesterton, Indiana
DISTANCE
1.5 miles
How to Walk Down a Sand Dune
The tricky thing is that the sand will slide away as you step on it. So you’re sliding as much as walking, but you’re doing both. You have to stay upright or your feet will slide out from under you. Once you get the hang of it, it’s pretty fun.
Walt Hoel, REI
River to River Trail
IN 2020, MOST OF the trail-running races were canceled. Athletes turned to the website Fastest Known Time to compete against a clock instead of each other. No female had attempted to set an FKT on the River to River Trail, near me. I thought, We gotta get some girl power going on here.
In April 2021, I set the FKT for a supported through-hike at two days, 17 hours, and 35 minutes. In accordance with my desire to pursue the next hardest thing, I wanted to see if I could complete it without any assistance—self-supported. That’s 50 miles a day of rocky, gnarly terrain with a heavy backpack containing everything I would need. I cached seven boxes of supplies along the rail the week before.
You have to go in April before the horses tear up the trails, the ticks get too thick, and the trail gets overgrown. But it’s still freezing at night. I figured my chance of success was 50 percent.
At 8:24 a.m., I dipped my toe in the Ohio River, the ceremonial start. My plan was to run the flats and downhills and power-hike the uphills. On the first day, my sleep system was at my cached drop at mile 50.3, so I had no choice but to make it that far.
Filtering water takes a long time, and I was rationing so I didn’t have to do it very often. This was a terrible move. Hydrate, don’t diedrate. At the Garden of the Gods, I walked out to the amazing overlooks, appreciating the sunshine blanketing the vast expanse of wilderness and watching pine trees dance.
At Owl Bluff overlook, I turned off my headlamp and looked at the stars. They were brilliant. I could hear Lusk Creek below. I breathed in the chilly air, held it, and calmly exhaled into the night. I had this. The descent down to the creek was difficult and slow-going, but when I reached the banks, I stood in the cold water and let it work its anti-inflammatory magic on my tired legs. By the time I reached my drop spot, my legs were stinging through their entire thickness and my shoulders were giant balls of anger. Sleep did not come easy until 2:30 a.m.
The next day, the trail was not in good shape and not runnable. My left shin was waxing and waning with sharp pain. My shoulders had accepted their fate as load-bearers, and my trapezius muscles had formed into crunchy, hard buttress balls beneath my pack straps.
I had almost a marathon to go before I could sleep. I started to get overwhelmed and tried to focus on the mile I was on, to be in this moment. But throughout the night, I encountered a maze of gargantuan pine trees and later got off trail. It was exhausting crawling over, under, and around the down brush and bushwhacking through thorns. By 1 a.m., I still had four hours of moving left. I was exhausted and in so much pain. I was digging my hiking poles into the steep gravel incline and pulling myself up with my arms. But I knew if I made it to my resting spot that night, I would be about to finish, even if I didn’t set the FKT.
I made it around 5 a.m, slept for a couple hours, then set out on the last 50-mile stretch. I ran and hiked all day and all night to give myself a chance to finish in under three days. Long after dark, I was moving fast on a 6-mile section with sharp drop-offs. I talked myself through it out loud: left, right, left, right, no whammies. Left, right, left, right, no whammies. The scariest hazard for me was losing the trail and falling into a ravine.
About 7 a.m., the cold was stealing every last ounce of energy I had. I tried to focus on the sunrise, its brilliant yellows and oranges bathing the bottomlands near the river.
I rounded the turn, and the large Grand Tower River to River sign came into view. I smiled ear to ear. I stopped at the sign and laid my head against it.
On the river bank of boulders and rebar, I sat down on a rock. After two days, 23 hours, and 43 seconds, I dipped my toe into the Mississippi.
I was so grateful that I have a body that can do that and a mind that wants to. Even though I was in pain and it was too cold and I was alone out there, the trail magic was with me. I was thinking of John O’Dell, the trail’s founder, who had died the previous year, and Bill Gilmour, who runs the River to River Trail Society and tries so hard to maintain this place. The people rooting for me and the people who love it as much as I do. That took me to the end.
Later, a guy messaged me through FKT and said he was going for the record because there’s no way a girl had the fastest time. He only made it 20 miles. —Lindsey Godby-Roberts, 39, competitive trail runner and manager of Run to Succeed Sports
WHERE
Elizabethtown to Grand Tower, Illinois
DISTANCE
160 miles
Owen-Putnam State Forest
TRAIL RUNNERS and ultra runners try to find the hardest thing possible. That’s how they get their kicks. The Owen–Putnam State Forest is where the Indiana Trail Running Association has a 50-mile race. I was the director for a few years, and I coined it the toughest race in Indiana. It’s straight up and down, you’re taking lots of water, and it’s all horse trails, which can be very muddy. —Terry Fletcher, founder of the Indiana Trail Running Association
WHERE
Spencer, Indiana
DISTANCE
18 miles
Spelunking
Mammoth Cave
IT IS KIND OF scary when you’re down there and you get to an especially dark place. If you ever have the experience to be in a cave where they are completely cutting off the lights, and you just get to sit there in absolute darkness, that is a type of darkness that you really can’t experience above ground, just by virtue of the fact that we have light and sunlight.
One of the interesting things about the cave is the tuberculosis clinics that they had where it was believed that the vapor in the air inside of the cave was really beneficial for TB patients. They ran a clinic down there where people with tuberculosis would stay, but I don’t know if that helped scientifically or medically. It was a really interesting thing to get to see aside from the natural features of the cave itself. —Sarah and Tim Puckett, 35 and 44, respectively; travel adventurers
WHERE
Kentucky
DISTANCE
1–6 hours
How to Make a Palmer Furnace
Cavers never leave home without a garbage bag to ward off hypothermia. Poke holes in the bag, put it on, and squat over a lit candle. The hot air will warm the inside of the bag. We are almost always wet, and we don’t have the luxury of being able to move around. It’s also a great trick if you get cold while backpacking.
Laura Demarest, Bloomington Grotto
Caving in Southern Indiana
I’VE BEEN CAVING since 1999, when I was 15 years old. Now I’m a rescue instructor and the chair of the Bloomington Grotto, an organization for cavers. The caves for the Grotto visits are on private land, and we have special permission. There’s one with reflecting pools that are just stunning, formations fewer than a dozen people on Earth have seen, underground rivers that we kayak to get to our starting point for exploration. There’s one with a drop of 145 feet. We do a trip every month, and we’ll get you to the exciting places—with a group of people who aren’t all looking at their phones. —Laura Demarest, 38, watershed coordinator
WHERE
Various private locations, Indiana
Paddling
Kayaking Across Lake Michigan
I’M THE ONLY person who has paddled solo across Lake Michigan six times. Last summer, I did it three times within 33 days. I don’t tell more than a couple people before I leave because I don’t want them to worry. No one thinks it’s a good idea.
But I love having the lake to myself. For about 40 miles, it’s all mine. No boats, nothing besides shades of blue. When the wind’s not moving, the lake is like glass. It’s just incredible. One big reason I do this is to inspire adventure in others through my photography.
The first time, I left at 3 p.m. and paddled overnight because the lake is typically calmer in the evening. Paddlers don’t train on lakes, so they don’t appreciate how challenging it can be. On a river, you have the push of the current. On a lake, it’s all you. Crossing Lake Michigan takes about 13 or 14 hours, and it’s all about endurance and hydration. If I don’t hydrate properly, my abs lock up and it’s very painful. I want to get out and stretch, but that’s not an option.
You have to be really skilled to push out any doubt or fear. Once it creeps in, you expend a lot of energy and risk doing something foolish. In an open-sea kayak, without an outrigger, if you stop and lean over, you’re going to tip. You cannot stop and relax—you have to sit straight up and balance for 13 or 14 hours. People are fearful of big waves. Getting tired. Freighters going to Chicago or Gary. And if the weather changes, there’s no way to get off the lake fast.
One time, I forgot my compass. I had to navigate with the sun, and that was a little nerve-wracking. Another time, there was an ugly wind that I couldn’t break through, and I didn’t make any progress for an hour. I finally had to sprint for two hours. The lake is really strong. I don’t take it lightly.
Last year was supposed to be the final crossing. But I’m already thinking about number seven—and I want to be the first person to do a roundtrip paddle. I love Lake Michigan—she’s my friend. When you see the lighthouse and finally crash on the beach, it’s quite the accomplishment. And after all that time alone, you realize maybe you really do need some people.
—Mike Stout, 61, marketing consultant and blogger at thenorthlandadventurer.com
WHERE
Two Rivers, Wisconsin, to Ludington, Michigan
DISTANCE
50 miles
Canoeing the Pine River
THAT FIRST DAY, I was like, What have I done? There are no straight points on the Pine, and it’s fast. There’s never a time when you’re not paddling. It’s not a trip where you relax and hang out and look at the views. It takes ultimate teamwork in terms of paddling with someone in a canoe with all of your gear for three days of camping. If you go in, all your stuff gets wet, you’re freezing cold, and you’re in a national forest probably 4 or 5 miles from a road. You’re screwed. It can make or break a relationship. We bickered a lot because we were both stressed, but the second day, we got into a groove. Saw probably 15 bald eagles, watched one grab a salmon and eat it. The rewarding part is when you lie down that night and you instantly fall asleep. —Cahmelan Porter, 33, fashion designer and avid outdoorsman
WHERE
Huron–Manistee National Forest, Lower Peninsula of Michigan
DISTANCE
Up to 45 miles
Steelhead Trout Fishing
I’VE BEEN FISHING the St. Joe River in Northern Indiana for 30-some years. It’s one of the premier places for steelhead trout, and the season is November through spring, so the water is ice-cold and you have just a tiny chance of catching something. But sports fishermen love the physical and mental challenge this presents. The fish are pretty “athletic” and can jump 4 feet in the air. You really have to muscle the thing in. —Mike Axl, 36, owner of Moving Water Outfitters
WHERE
St. Joseph River, South Bend, Indiana
THE LOWER SECTION of Christiana is just fabulous. You start at Willowdale Park in Elkhart, go downstream, and in only one-and-a-half miles, it joins with the St. Joe River for another half mile. You take out at Beardsley Park. This is one of the only natural whitewater sections in Indiana. The rapids are only Class 1 unless it’s really streaming, but it’s a relatively narrow river and the turns are so sharp. There’s one called a Screaming Right-hand Turn. If you don’t make that turn, the river is going to slam you sideways into a cement wall. There are some 4- to-8-inch drops, where you steer and bounce and have fun, but there is also a massive 4-foot drop. At the end, you pop out less than half a block from the massive Johnson Street dam that they are still using for electricity. There’s monstrous bubbling of water and you’re hitting it at all angles. It’s an absolute ball. But I have 20 years of experience and 3,000 hours in my whitewater boat. What I do for kicks could be hard and dangerous for other people. This is not a place for someone whose beer cooler costs more than their kayak. —Margaret Easton, 61, water trails representative for the Indiana Department of Natural Resources Trail Advisory Board
WHERE
Elkhart, Indiana
DISTANCE
1.5 miles
Apostle Islands National Lakeshore
APOSTLE ISLANDS National Lakeshore’s towering sandstone cliffs may be one of the favorite places I’ve ever dipped a paddle. But there’s a reason why local kayakers call Lake Superior “the boss.” Powerful lake currents make paddling difficult on the most pleasant of days, and the weather can turn from delightful to dangerous in moments. The search-and-rescue teams here conduct an average of 10 serious operations each year; not everyone makes it back. On my last visit, I signed up to do a sea-cave kayaking tour with local outfitter Trek and Trail. What started out as a sunny, bluebird day suddenly took a foreboding twist. We’d just exited our first cave when a squall hit us. Paddling into the wind was like pushing against an invisible wall. If the waves had risen further, they could have easily capsized our 16-foot sea kayaks, and, if things went further south, either swept us out further into Lake Superior or battered us against the cliffs. My group was inexperienced and their faces showed it. That included our guides; after chatting with both of them earlier, I learned this was their first year on Superior. When the guides correctly decided to return to the beach, I felt a mixture of disappointment that we wouldn’t continue exploring the sea caves and relief knowing we wouldn’t add to search and rescue’s burden. —Robert Annis, 49, national adventure writer and IM contributing editor
WHERE
Lake Superior, Wisconsin
Biking
Copper Harbor
I DECIDED TO explore Copper Harbor when I first read about it in a magazine. Someone wrote that it has world-class mountain bike trails and I was like, I am going up there—and I did. I had so much fun that I went back two weeks later and helped out at a mountain bike camp.
Copper Harbor has every kind of trail you can imagine, whether you’re a beginner or a pro rider. My favorite trail? Anything that is technical and super rocky. There is something about going there and being able to disconnect from the phones and social media while riding my bike with friends. I feel like I go home when I go there. Then, of course, I run into friends and go, ‘Oh, I didn’t know you were here!’ —Sally Marchand-Collins, 54, professional mountain biker
WHERE
Upper Peninsula, Michigan
Schooner Trace Trail
I’VE RIDDEN FOR about 30 years and have conducted technical skills demonstrations all across the country and the world. About 10 years ago, I started doing some racing and was featured in some magazine articles, so people began to recognize me, and when I’d go to these demos, people would pull me aside and say, ‘There’s a trail here that’s impossible. You should try it.’
When I’d go to Indy, I ran into the same girl two or three years in a row. She kept telling me about Brown County. ‘Man,’ she’d say, ‘I have the trail for you. I’ve never seen anyone clean it. It’s impossible.’ Honestly, I was a little bit of a trail snob at the time, and when she’d say that I’d think, How hard can it be? It’s Indiana.
The riding ended up being awesome. Schooner Trace actually became the whole impetus for my YouTube channel, where I travel all around the country trying to ride “unrideable” trails.
Schooner Trace is as challenging as anything I have ever ridden in my life. If you add a little moisture or water to the mix in some spots, you might as well be riding on rocks covered in motor oil. There’s almost zero traction and it’s a very technically challenging terrain—a double whammy. There are rock and root sections. Limestone. You are always putting out maximum effort to get through spots like that, but there’s very little time for recovery. Completing it requires a lot of punchy, physical exertion and anaerobic moves. You never really catch a good break.
It really opened my eyes. A great, technical challenge doesn’t have to come from a mountain bike hotspot out West that everyone knows about. It can come from anywhere. —Jeff Lenosky, 51, professional mountain biker and trail consultant at youtube.com/JeffLenoskyTrailBoss
WHERE
Brown County, Indiana
DISTANCE
4.1 miles
Crooked Creek Trail
THIS IS A VERY backcountry trail that was build by hand. I put in volunteer hours building it, and plenty of other riders did, too. There are lots of switchbacks, tons of logovers. We used the natural rock that we discovered when we were digging. It’s big, chunky, and challenging. The whole trail is hard. If you’re are a rider, it’s like Indiana’s version of Pisgah National Forest. People ask me all the time to coach them because they can’t get over the logs or make the tight turns. I know someone who races 100-mile events who can’t clean it.
—Kate Nolan, 50, owner of Brown County Bikes and professional mountain bike instructor
WHERE
Yellowwood State Forest, Brown County, Indiana
DISTANCE
5.6 miles
How to Do a Logover
Do a three-quarter stroke wheelie and land your front wheel atop the log. Allow your wheel to roll slightly forward. Unweight your rear wheel. Extend your arms forward and move your hips back. Practice this before you take it to the trail. You can use a curb, speed bump, or wood. Get your timing down and commit this to muscle memory so you’re dialed and ready to roll.
—Kate Nolan, Brown County Bikes
Griffin Bike Park
GRIFFIN Bike Park for mountain biking and trail riding is really cool. It gets a lot of national attention. People come from around the country to ride over there. They have some warrior trails, or adaptive trails, which is rare. I’m blind, so I rode on a hand-crank cycle following a paralyzed guy, just following his sounds. I’ve also been on the back of my tandem bike with a headset, following instructions. I’ve taken others out there and have watched the thrill come back into their life. They can go up and down these trails just like everyone else. That’s really cool. —Lonnie Bedwell, 57, motivational speaker and extreme-sport athlete
WHERE
Terre Haute, Indiana
DISTANCE
Various distances
Climbing
Governor Dodge State Park
IT’S REALLY REWARDING when you get up there and you are alone. I think I cried when I got to the top of one of the rocks at Governor Dodge for the first time. I wouldn’t say it was exhausting, but it can be a little frustrating if you can’t make any progress while climbing. The biggest challenge is that it’s outdoors and there are not as many rules as there are in indoor climbing. You have to figure out your own way of getting to the top. —Canhui Yu, 27, amateur climber
WHERE
Dodgeville, Wisconsin
The Holy Boulders
THE HOLY Boulders was really a unique little experience because it goes 45 minutes into the middle of nowhere. You park on the side of the road and hike into the woods. That’s something that is purely unique to rock climbing because there’re not a lot of hobbies where you just go out into the middle of nowhere and hope that you end up in the right spot.
The Holy Boulders is broken down into areas so there’s the Illuminati boulders, the Star Wars Boulder, Mollusk, and so on. Each boulder has its own routes up to the top of it.
When I went there for the first time, the trail that they had wasn’t very established yet. We took this old way following a creek and the biggest challenge was probably not getting lost on your way in there because it’s tucked back in the woods. —Sean Hendershott, 21, amateur climber
WHERE
Pamona, Illinois
DISTANCE
Devil’s Lake State Park
Devil’s Lake State Park
I USUALLY CLIMB based on how fun the rock looks, and that’s exactly what I did at Devil’s Lake. For me, what was really cool about Devil’s Lake is that I am pretty used to quartzite, which is the type of rock there. They keep the rock extremely traditional by not bolting anchors. You have to set your own anchors and clean them.
I approach climbing with caution so that’s why I climb a lot of really easy routes. But, here, trying to find one that was easy was actually difficult. —Maiza Lima, 34, amateur climber
WHERE
Baraboo, Wisconsin
