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Ski Resort Life

Weekends: Devil's Head, Wisc.

Leave behind the bright lights of Chicago for a weekend and head to the haven that is Devil's Head.

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Located on the glacier hewn Baraboo Bluffs that tower over Lake Wisconsin near Merrimac, Devil’s Head Resort has been a haven for Midwest skiers since 1970. The secluded resort draws skiers from all over the region, but it’s a haven that’s particularly luring for Chicago’s skiers, simply because Devil’s Head is everything Chicago isn’t: pristine, serene and relaxing. From the Loop to the slopes is about three hours, a trek thousands navigate every winter.

The skiing is expansive by Midwest standards, with 28 trails and 10 lifts spread over 300 acres, enough of that legitimate, albeit not thigh-screaming, steeps that will keep things interesting.

The sprawling three-winged, two-story lodge and base area includes six restaurants, lounges with live entertainment and facilities for childcare (and the popular Kid’s Night Out program). Ongoing improvements, led by brand-new Glacier Ridge Condominiums, add higher-end ski-in/ski-out options to the lodging mix—a first for modest Devil’s Head, and as good a reason as any to settle in for the weekend.


Blow out of Chitown by late afternoon on a Friday, beating the rush up I-90 past Rockford and around Madison. Devil’s Head gives all its slopes a fresh grooming at 6:00 PM, so early arrivals score first tracks as the night skiing lights come on.

It’ll be cold, so keep it brief by skiing the block of blue cruisers at the southern end of the mountain. Dante’s Inferno and The Cauldron, both of which snake downward in broad sweeps from the top of the Number 1 chair, offer a preview of Saturday’s coming attractions. Cap it off with shots down Devil’s Alley off the 00 chair, a black diamond that’s fast and narrow. Warm in the hot tub before taking the short walk to a casual dinner at Dante’s, in the main lodge, followed by a scotch next to the fire in the Devil’s Den bar.


Today you’ll ski the entire mountain, so fuel up at the breakfast buffet at Dante’s Restaurant in the main lodge. Try the French toast—sourdough bread dipped in cinnamon-vanilla custard with side of applewood bacon.

Seek your first tracks on the far edge of the resort along Devil’s Playground, and then work over to Devil’s Alley, The Cauldron and Dante’s Inferno—familiar from last night. When the day skier traffic picks up, start moving toward the middle of the trail system.

The center runs are the most popular at Devil’s Head: a half-dozen blacks and a monster terrain park fed by five chairs, so head here early and plan to spend some time. Charge down Cyclops, an expert boulevard perfect for wide arcs at mach speeds in the middle or fall line slaloms along the tree-lined edges. Another black, Devil’s Air Park, used to feed into Cyclops, but it’s been extended all the way to the bottom for this season, so a scouting foray is in order. If you’re so inclined, hit the Zone terrain park at the summit. Afterwards, get a little Revenge, a tight black-diamond that funnels down to the Number 4 chair.

Stop for lunch at Smokies, at the bottom of Revenge. An on-hill eatery and bar with a massive circular fireplace, Smokies serves a gigantic steak sandwich smothered in cheese and mushrooms that’s nearly legendary here. Tack on a Wisconsin microbrew favorite, Spotted Cow, if you’re in the mood.

Make your way to the Number 4 ¼ chair after lunch, home to Roundabout, a testy little black-diamond that winds through the trees. You might feel the beginnings of thigh burn, but the biggest challenge at Devil’s Head awaits. Double-black Outer Limits, usually crunchy in the morning and sometimes mogul strewn by later in the day, is a feisty run that just might surprise you. Head back to the base for a game or two of darts and a bucket of icy beers at the Avalanche Bar & Grill.

For dinner, make a reservation at the Cornucopia Room in the main lodge. Pastas and steaks are menu staples, but the pan-seared sea scallops with spiked citrus salsa is a house special.

Top off the ski day off with a horse drawn sleigh ride and then enjoy a nightcap at the Devil’s Den bar, where there’s a party going every Saturday night with live bands and taps through which the local favorite, Leinenkugel ale, flows like there’s a direct pipeline to the brewery.


Sunday morning is perhaps the most sublime skiing of the week art Devil’s Head. Day skiers and the previous evening’s partiers don’t make it to the slopes until around 10, so the newly buffed carpet is the exclusive playground for early risers.

Breakfast again at Dante’s, this time setting the hearty tone for the morning with a Monte Cristo: roasted turkey, smoked ham and Swiss cheese between slices of sourdough bread dipped in egg batter, fried golden brown and served with wild berry dipping sauce.

For something unique, rent a helmet cam to record the morning’s events (lower level of the Cliffhaus day lodge; $14.95). Then beeline to the mountain’s mid-section and that pod of groomed black-diamonds, grabbing freshies by the trees on either side of the trail as the morning progresses. With the late comers finally rousing, duck into the Cliffhaus Café for a bowl of soup and a sandwich before hitting the road back to the Windy City, where the pace is far more blustery, indeed.

SIGNPOST: Devil’s Head, Wisc.

300 skiable acres; 500 vertical feet; 100 percent snowmaking; 40 annual inches; 28 trails; 10 chairlifts. Lift tickets: $45, kids 6-12 and seniors 60-65 $38, kids 5 and under and seniors 66 and over ski free.

Getting There:

From Chicago, take I-90 west toward Rockford. Continue into Wisconsin to Madison where I-90 merges and becomes I-90/94. Follow I-90/94 west to Exit 108a , Highway 78 south. Follow Highway 78 for 8 miles, turn right at Highway DL and continue 2 miles to Bluff Road. Turn right and follow to the resort entrance.

Info:; 800-472-6670.