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Chicago cycling enthusiasts are lucky to have the lake path not far from their front doors. But at a certain point (usually a few minutes into a ride), dodging potholes, Rollerbladers, dogs and pedestrians becomes a real buzzkill. To the rescue: Hours of continuous riding just a three-hour drive away in southern Wisconsin, where you can hit some of the same paved paths and dirt-road trails proposed for cycling competitions if Chicago lands the 2016 Summer Olympics.
The whole area would likely be involved in the Olympics. Time trials could be held in Madison with some mountain bike events unfolding at the nearby Tyrol Basin ski area. Several high-profile (and high-intensity) cycling events already take place in the area, including the Horribly Hilly 100, which climbs the tortuous, legs-will-scream Mounds Park Road in Blue Mound State Park.
You’ll find smooth, beginner-friendly riding on the Military Ridge State Trail. It begins in downtown Madison, but unless you have the stamina of Lance Armstrong, join it a little west of the city. A former pioneer trail that’s now paved, this ridge-top path is mostly flat, but mild hills and valleys along the way keep things just interesting (and challenging) enough. At the town of Mount Horeb (25 miles west of Madison), veer off and refuel at the Grumpy Troll (105 S Second St, Mount Horeb, 608-437-2739). The popular pizzeria and pub brews its own beer (grab a growler as a souvenir). While you’re walking off that ’za, check out the statues of trolls all over town and the Mustard Museum (100 W Main St, 800-438-6878).
Get back on the bike trail and continue west—in about five miles you’ll find Little Norway, a replica of a Norwegian town ($12 adults, $5 kids). Soon after, you’ll reach Blue Mound State Park. Beloved to mountain bikers thanks to six miles of dirt trails offering scenic views of the surrounding countryside, this 1,153-acre park is perched on the tallest hill in southern Wisconsin and offers other activities such as swimming, a nature center and shaded picnic areas. There’s a $4 per day trail-pass fee for cyclists over 16. Hiking is free.
Now take a deep breath and get ready for some off-roading: No worries—three of the dirt paths are a cinch for beginners. Start with flattest, shortest loop—the John Minix Trail. The one-mile trek is over mostly hard-packed dirt and gravel and takes about ten minutes of easy pedaling to complete. The Willow Springs Trail and the rolling Pleasure Valley Trail are two miles and pass through sugar maple trees, an open prairie and a wooded valley. These loops each take about 25 minutes, but budget extra time to take in the surrounding countryside.
More advanced riders should branch off to tackle the steep climbs and rough terrain of the three-mile Single Track Trail. This path offers spectacular views of the dolomite and chert outcroppings and challenges bike-handling skills. (All paths can be reached from the trail head at the pool parking lot, in the middle of the park.) Serious riders will also enjoy the climbs and rougher terrain of the Governor Dodge Trails farther to the West, or the Ferry Loops north of Madison.
Back on the Military Ridge State Trail, more goodies await. As you spin by the midsize towns of Ridgeway (known for its folklore village) and Barneveld (where the Botham Vineyards happily offer tastings), you’ll encounter tiny towns—typically a short half mile off the trail—with shops hawking artisanal cheese, fresh fruit and more. Peel off and explore—that’s half the fun. The path finally ends in Dodgeville, where you’ll find a courthouse built in 1859 as well as the award-winning Uplands Cheese Market (5023 State Rd 23, 608- 935-5558).
Sun-weary and pedaled-out, it’s time to put those feet up. Consider staying the night at the Deer Valley Lodge near Barneveld, where rooms start at $119 a night and a mini water park offers a whirlpool for soaking sore muscles (401 W Industrial Dr, 888-924-1601). Or rough it in a tent at Blue Mound State Park ($12–$17 a night, 888-947-2757). Armed with treats from the country and a healthy dose of exercise, you should be recharged and ready to face the city again. But be careful, it’s a jungle out there.
Ready to roll? Visit travelwisconsin.com for trail maps and directions. Rent bikes at Yellow Jersey in Madison, Wisconsin (419 State St, 608-257-7733).