Five Summer Trips for Adventure Seekers in Chicago

Montana wilderness, Utah mountain biking, and Wisconsin rock climbing—it’s all just a few hours’ drive or flight away.

Photo: David Fenton

The digs at Paws Up in Greenough, Montana

Greenough, Montana

Glamp it up in Big Sky Country

Paws Up (800-473-0601, pawsup.com; from $1,075 for two adults, includes three meals and airport shuttle), the 37,000-acre working cattle ranch resort that started the glamorous camping—“glamping”—craze, recently upped its game. Opening this month, the new six-tent Cliffside Camp sits high on a bluff with views over the Blackfoot River, made famous by Brad Pitt in A River Runs Through It. The resort’s 30 palatial safari-style tents—equipped with everything from bathrooms and electricity to swank knobby furnishings and a camping butler—book up fast. A good alternative is one of 28 grand wilderness homes, some with a private tent in a four-acre yard. The roster of activities is just as enticing: guided fly-fishing ($450 for one or two), whitewater rafting ($165 for adults, $120 for children 5 to 11), chuck wagon dinners ($50 for adults, $35 for children 5 to 11), clay shooting ($175), and a cattle drive ($375 a person), in which Black Angus trot along rolling green fields framed by peerless blue skies while cowboys show you how to drive and sort, nice and easy. The summer sun sets late, leaving plenty of time to kick back with a local bourbon on your own giant porch.

  • 3.5 hours by plane
  • Splurge
  • Good for families

Baraboo, Wisconsin

Climb the craggy face of nature

The shining star of Baraboo for its immense lake and endless hiking trails, Devil’s Lake State Park also offers some of the best rock climbing in the Midwest. Most of the park’s 2,000 climbs scale durable quartzite, which resists erosion and keeps classic routes intact. Views from the bluffs are pretty splendid, too. Try your hand at the sport under the tutelage of the competitive climber Easton Dreher. He runs the outfitter Vertical Illusions (608-253-2500, verticalillusions.com), which gives guided rock-climbing and kayak tours at the park. Sign up for a day of climbing ($180) and you’ll get all the basics, from bouldering to pulling on jugs (the easiest, biggest holds). Stay overnight in a camp setup by Vertical Illusions (from $250, including kayaking the next day), or take the civilized path at the Inn at Wawanissee Point (608-355-9899, innatwawanisseepoint.com), perched high on a bluff just beyond the park gates. At the inn’s wine and cheese hour, toast your athletic prowess with a glass of Wollershiem Winery’s Prairie Fumé (800-847-9463, wollersheim.com), an award-winning locally made Seyval blanc.

  • 3 hours by car
  • Good for families
  • Beach

Anderson, Indiana

Learn how to tame the wild

As veteran campers know, self-sufficiency is its own reward. Bolster your know-how at the 21-acre Willow Haven Outdoor (317-703-9655, willowhavenoutdoor.com; $379 for adults, $179 for children 10 to 17), a fun setting for survival training for the family. Owner Creek Stewart focuses on real-life scenarios (managing in a tornado, say, or getting lost on a hike) and the skills to meet four core needs: shelter, water, fire, and food. You’ll learn how to build shelters, carve spears, forage for edible plants, and—yes!—make fire with sticks. Comfy lodge digs with bunks are included, so you won’t have to rough it all weekend, although camping is welcome. The day after, return to modern life with a feast, cocktails, or an overnight stay at the new Alexander (317-624-8200, thealexander.com; from $199), located 45 minutes away in downtown Indianapolis. You won’t even have to leave the hotel to grab some culture: It is currently displaying more than 250 works of art curated by the Indianapolis Museum of Art, as well as a garage deliberately vandalized by a British graffiti artist.

  • 3 hours by car
  • Good for families

Monterey, California

Commune with marine life

Imagine the Grand Canyon plunging more than 13,000 feet below the Pacific, and you have the largest deep-sea gulch off the west coast of North America. This draw for a spectacular abundance of marine life is mere miles from Monterey Bay. Often overshadowed by its neighbors to the north (San Francisco) and south (L.A.), and an hour’s drive from the nearest big airport (San Jose International), Monterey requires a bit more work to get to. But the payoff—a rugged, remarkable Pacific coast haven—is worth the effort. Bring the kids and book a room at InterContinental The Clement Monterey (831-375-4500, ictheclementmonterey.com; from $209) on Cannery Row; head down the street to the oceanfront Monterey Bay Aquarium (831-648-4800, montereybayaquarium.org), where sea otters frolic in their newly refreshed abode. Spot elephant seals, sea lions, and pelicans while kayaking in the calm waters of the bay. Or catch the summer migration of humpback and blue whales aboard a whale-watching cruise led by a marine biologist (831-375-4658, montereybaywhalewatch.com). Drive 15 minutes south to stand on higher ground at Point Lobos State Natural Reserve (pointlobos.org). Explore the Whalers Cabin Museum before taking an easy hike with outrageous ocean views.

  • 4.5 hours by plane
  • Splurge
  • Good for families
  • Beach

Park City, Utah

Capture views atop two wheels

Come summertime, the world-class ski slopes of Park City (home of the Sundance Film Festival) make for possibly the best mountain biking in the world: The region is the only one to hold the International Mountain Bicycling Association’s highest designation. Offering 400-plus miles of wild trails, the area is enticing for bikers of every skill level. Beginners can meander across bluffs and through Gambel oak on the Round Valley Loop trail. The aerobically fit should tackle steep Wasatch Crest, which climbs to 10,000 feet and delivers outstanding views of both sides of the Wasatch Range. For the best of both worlds, hitch a ride on one of the three big resorts’ chairlifts to connect with Park City’s remarkably well-linked trail system. At Deer Valley Resort (800-424-3337, deervalley.com; rooms from $124, chairlift rides from $28), intermediate bikers can take the lift to the 24-mile Mid Mountain trail, which rolls around at a fairly consistent altitude of 8,000 feet. On June 22, catch Savor the Summit (savorthesummit.com; from $40), the popular outdoor dining festival where local restaurants serve their best dishes on one long table down Main Street. Stay a street over at the luxurious Washington School House (800-824-1672, washingtonschoolhouse.com; from $295), an 1889 schoolhouse turned into a 12-room boutique hotel, where summer prices are less than half the cost during the winter peak.

  • 3.5 hours by plane
  • Splurge
  • Good for families

 

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