Toughest Area Races


Many runners think of the Windy City as a great place to PR. Flat and temperate, Chicago athletes often have to run faster or farther to find new challenges. But not always. Sometimes natural, sometimes contrived, the challenges these races provide are always tough. Whether you want something on the road or in the wilderness, something long and hard or short and fast, something hot or something cold, a good old fashioned race or a last-man standing stage event, you’re bound to find what you’re looking for in one of these five races.


March Madness Half Marathon, March 20, Cary, IL

Race director Phil Bush says he and his staff, “try to make everything but the race easy.” Still, one of the more challenging aspects of the March Madness Half Marathon is that it often sells out in under an hour. Bush says that the race has, “some of the biggest hills in the Chicagoland area,” including Substantial Hill, Lung Buster Hill, 10 Mile Hill (at mile 10, of course), Sneaky Hill at the halfway point and Big Hill to help close out the race. Because of the hills and the timing, the race is a, “perfect prep race for those runners going to Boston,” says Bush. On top of the hills and the winter training, local runners know that March weather is unpredictable. “We’ve had gorgeous and warm, cold and snowy, and blowing and rainy,” Bush says. Still, the race hasn’t been canceled for weather in 37 years.

In addition to a cleverly mapped course, runners can feel good about supporting the Hillstriders Scholarship. In memory of their former president and late running buddy Fritz Kauffman, the Hillstriders Running Club, which puts on the race, gives at least three $2,000 scholarships to college bound seniors who love the sport of distance running.


Rockdale Ramblin’ 10K, April 16, Rockdale, IL

Known in the 1970s and 1980s as the Toughest 10K in the Midwest, the Rockdale Ramblin’ 10K, like the March Madness Half Marathon, is known for its hills. Don’t let the name fool you, though. There’s nothing rambling about this jaunt along the Des Plaines River. Last year, times of 36:08 and 39:59 won the men’s and women’s divisions, respectively. While many runners would love to run times like those, you shouldn’t expect to PR on this course. Want an extra challenge? Run the Rockdale Ramblin’ 10K on April 16, the Sundowner 5K in July and the Run the Runway 1 Mile at the Joliet Regional Airport in October to join the run3 club. You’ll receive special run3 gear, be entered in a raffle and your combined time in all three races will compete with other run3 participants for overall and age division championship awards.


Quarryman Challenge 10 Mile, May 7, Lemont, IL

In the first two miles of the Quarryman Challenge 10 Mile, there is a 100-foot climb followed by a 140-foot descent and another 140-foot climb. Runners enjoy some relatively flat terrain before a 100-foot descent and climb back up between miles six and seven. It’s all worth it in the end, though. The last half-mile is a 100-foot fall to the finish. If that sounds like a lot of climbing, it is. Race director Dave Fako says that the Quarryman Challenge has, “more incline than any race of any distance in the Chicago area, with nearly equal amount of descent.” Your quads might be screaming the next day, but there will be plenty of days to glide along the Lakefront Trail this summer.

As if the hills weren’t enough of a draw, overall and age group winners take home unique, handmade trophies carved from the race’s namesake quarry. Those are, “the same stones used to build the Chicago Water Tower, Stockyard Gate, and numerous other historic buildings in the Chicago area,” says Fako. Historic downtown Lemont has a lot to display, as well. Runners pass, “the highest natural point in Cook County,” says Fako. Early in the course, runners see the Lemont Train Station, a stop on Abraham Lincoln’s funeral train, and the Old Stone Church, which now houses the Lemont Historical Society. “The church,” says Fako, “served as a Civil War recruiting station for Union soldiers. They were required to enlist 33 soldiers, ended up signing up 293 and only 63 returned.”

Run of the Dead Elimination Run, Oct. 30, Libertyville, IL

If hilly road races are too pedestrian for you, Run of the Dead in the Old School Forest Preserve in November might be more your style. There are three distances to choose from: 8.5, 17, or 34 miles, depending on how many times you want to run the 4.25-mile loop. Competitors have one hour to complete the loop. After an hour, everyone toes the line again in another attempt to complete the loop in less than 60 minutes. The faster you finish, the more time you have to recover before your next loop. If you fail to finish any stage in an hour, your race is over. “In between loops,” says Mike Brunette, founder of the Libertyville Running Club, “runners are provided a picnic area with food, bonfires, a crepe stand, massage therapists and music.” There’s also an aid station halfway through the loop, “stocked with soup, cookies, PB&Js, cupcakes, Halloween candy, salt tabs, beer, Gatorade, water, Coke, ginger ale, crackers, pickles and various other foodstuffs you typically find at an ultra race.”

If a massage and free crepes between loops sound dull, you’re welcome to stake your claim as the King or Queen of the Hill by running up and down a “rather intimidating sled hill just before the finish,” Brunette says. Last year, the male eight-loop winner ran up the hill 96 times, or an additional 10 miles. Don’t let such feats scare you off, though. “This race has a very laid back social atmosphere,” says Brunette. “Many runners and volunteers dressed in Day of the Dead theme. Due to the style of the event, there isn’t the serious competitive aspect of a typical road race.”


Frozen Gnome 10K/50K, January 2017, Crystal Lake, IL

Held in January every year, the Frozen Gnome is a 10K loop run once or five times, your choice. “The race is held on the beautiful and challenging trails of Veteran Acres and Sternes Woods parks in Crystal Lake,” says race director Michele Hartwig. The loop course means you’re never more than a couple of miles from Gnome Depot Aid Station, and there are a few other points at which your spectators and crew will be able to find you on the course. “The race,” says Hartwig, “has been blessed with volunteers that come every year to help athletes reach their goals. They bring homemade soups, warm smiles, and support.” You know running on the streets in winter means slipping on ice is inevitable. Next winter, take matters into your own hands and slide down Butt Slide Hill. Hartwig says, “You are either running up or down quad-building trails throughout the entire race course. Some are single-track trails. Others are open fields that a big gust of wind can blow snow around, and make it difficult to see in front of you.” The weather can be a huge challenge in this race, too. “Through the years,” Hartwig says, “we have had various conditions: deep fresh powder of snow that runners need to plow though, single digit weather that makes dressing to stay warm and perform without sweating a huge challenge, and slushy, ice covered trails that make it feel like you have weights on your feet.”

Still not sold? MUDD, the race’s organizing group, partners with the nonprofit organization Trails for Illinois ( whose goal is to support an Illinois where everyone lives no more than ten minutes from a safe and well maintained trail. Next year, when you’re warm and cozy on the couch, just remember, says Hartwig, “The ornery Frozen Gnome is daring you to take on this challenge.”