Illinois' Rustic Mountain Resort Is The Midwest's Hub For Year-Round Adventure And Stress-Free Relaxation

When it comes to skiing in the U.S., big mountain ranges and alpine villages often steal the spotlight: iconic Colorado spots Aspen, Vail, or Breckenridge, now known for its snow-dusted sculpture wonderland, come to mind. Perhaps you picture Mammoth in the West Coast's Eastern Sierra, or Vermont's Killington, one of the East Coast's most scenic ski resorts. Most wouldn't imagine the pancake-flat Midwest cornfields to be very snowboard-friendly. But for Midwesterners who can't make it to the mountains every weekend, there are surprisingly solid slopes closer to home. One of Flyover Country's best-kept secrets is Chestnut Mountain Resort, a year-round playground in the northwestern corner of Illinois. 

Perched high on limestone bluffs overlooking the Mississippi River, Chestnut is Illinois' premier ski destination, with 19 trails, 9 lifts, and a 7-acre terrain park, complete with its own lift and plenty of jumps and custom features. Though the mountain's vertical drop is only 475 feet — modest compared with, say, Colorado — don't let that fool you. Black diamond trails like War Path and Mine Shaft — are exhilarating runs that feel like plunging straight off the mountain without excessive flat ski-outs at the bottom. The charming Tudor-style lodge offers over 100 rooms with snowy vistas and all the cozy après ski essentials: jacuzzi, sauna, hot chocolate, and cocktails.

Chestnut Mountain is located just outside of Galena — a picturesque, historic town brimming with cozy inns and boutique shops, packaging Chestnut Mountain as a surprisingly complete ski experience. Across the Mississippi River, upriver from Galena, lies Iowa's oldest city, Dubuque, with an underrated riverfront downtown and the closest airport, approximately 30 miles away. However, flights through Dubuque only connect from Chicago, so you'll find more options flying into Rockford International Airport, 80 miles east, or Chicago O'Hare International Airport, approximately 150 miles away.

Years before snow enthusiasts took to the slopes above the Mighty Mississippi, glacial movements that flattened the rest of the region somehow bypassed this area, leaving craggy cliffs and limestone bluffs across several counties. The unique, leftover topography defines the Driftless Area, which encompasses Chestnut Mountain. The Fox and Sac were among several Native American tribes who lived or traveled through the region. Nearby Galena boomed in the 1800s around mining "galena," a local lead ore, and became a thriving steamboat hub. Later, skiing surged in popularity post-WWII,  and Chestnut Mountain Resort opened in 1959.

This Driftless terrain at Chestnut is rugged and rocky, with runs carved into slopes so steep that some of the black diamond trails feel shockingly precipitous. It's the highest ski resort in Illinois, with the state's highest ski lift. Old Main is a wide green run flanked by rock walls, while Crazy Horse, a blue trail, winds playfully around the mountain's south side. The resort's spacious ski center provides gear rentals and a souvenir shop with anything else you might need. With 40% of the slopes considered beginner terrain, Chestnut's accessible to all levels, and offers private or group ski and snowboard lessons too. 

A weekend lift ticket costs about $80, as of this writing, but go during the weekday if you can for fewer crowds. Check the wind and weather conditions before you go: Thanks to its perch above the river, Chestnut can get especially windy and particularly cold. On-site après-ski options abound, from beer or hot chocolate and cheese curds at the Summit to scenic, upscale dining at Sunset Grille. For quicker bites, the Mountain Top Cafe is perfect for a mid-day refuel.

Chestnut Mountain can be just as fun without snow. Ride a chair lift to the top of the resort's Alpine Slide, then zoom down 2,050 feet with views of the Mississippi River the whole way. For a higher vantage point, try the Soaring Eagle zipline, an 800-foot ride offering an eagle's-eye view. Unlike traditional ziplines, this one features a chair-style seat for extra comfort. "Activities were fantastic, alpine slide was very fun, Eagle zipline ride was too! My son loved it," wrote one Tripadvisor reviewer. There's an on-site nine-hole disc golf course free for lodge guests — or $5 to the public, as of this writing. If you prefer something a little more classic, there's an 18-hole mini golf course. Kids may enjoy the Chestnut Mining Company, where they can "pan" for gems in a hands-on tribute to Galena's mining history and the site of America's first 19th-century "mineral rush."

Head to Farside Bike Park, one of the region's biggest lift-served mountain bike parks. With four black, three blue, and two green trails — plus a beginner area — there's terrain for all skill levels, and bike rentals are also available. "100% worth the trip," said one reviewer. "The chairlift setup is awesome, custom bike racks only touch the tire rubber on your bike ... Park features are advanced and extreme."

Mississippi River boat cruises offer a relaxing way to spot wildlife and learn local history. Each 1.5-hour ride includes an Alpine Slide trip or Scenic Chair Ride as well. To round out your visit, try a Segway tour — a 3-mile, off-road ride through scenic hills. Of course, Chestnut is less than 10 miles from historic Galena's charming downtown, where you can shop or hit up local wineries and trails.