TRAVEL: 51 MILES
Stick your feet in the sand and feel your city stress fade at Indiana Dunes National Lakeshore (nps.gov/indu), a 15,000-acre park on the southern shore of Lake Michigan. Or get your adrenaline fix by signing up for kiteboarding lessons with Chicago Kitesurfing ($150; chicagokitesurfing.com), then pitch a tent at one of the park's 78 campsites.
TRAVEL: 99 MILES
Hammer the 30 miles of singletrack that lace the glacial hills of Wisconsin's Kettle Moraine State Forest (dnr.wi.gov). The John Muir trails are the most popular, so skip them. Instead, ride the 8.4-mile Emma Carlin loop and the ten-mile Connector, which are more technical (steeper, with more mini-boulders and roots) than the Muir but see only a fraction of the riders. And bring your road bike, too: BackyardBikes.com features printable, user-friendly guides to two dozen popular paved routes throughout the state forest. Bed down beneath stands of old-growth hardwoods at one of two walk-in car-camping sites at the Ottawa Lake campground (dnr.wi.gov), or head to Lake Geneva's Bella Vista Suites for fluffy robes and a private balcony overlooking the lake (doubles from $189; bellavistasuites.com).
TRAVEL: 145 MILES
Book yourself an Immersion Suite at the Kohler Waters Spa (doubles from $663; destinationkohler.com), in Kohler, Wisconsin. With plasma TVs, whirlpool baths, and a dozen in-room treatments to choose from, you'll never want to leave your Eastern-influenced pad. Bonus: This December, Kohler will open a satellite spa in Burr Ridge, Illinois, a scant 19 miles from downtown.
TRAVEL: 210 MILES
Nymph, single-hand fly-fish, or learn to speycast (it's an artful, two-handed technique) for 20-pound steelhead on Michigan's wide-open Muskegon River with local expert and Gray Drake Lodge owner Matt Supinski (doubles $500, including guiding and lessons; graydrake.com).