Salida, Colorado
Think of Salida (pop. 5,000) as a ski hub without a resort—the nearest hill is the underrated, overpowdered Monarch Mountain, 20 minutes away. Which means residents of this unpretentious, bike-friendly town can take advantage of 12 nearby fourteeners, the Class III–IV Arkansas River, which runs through town, and epic mountain biking on the Monarch Crest Trail—without Aspen home prices.

Leavenworth, Washington
At first glance, the Bavarian-themed buildings that line downtown Leavenworth (pop. 2,100) might strike you as kitschy, the kind of architecture that's made for tourists. But crack-climb on the granite cliffs of nearby Tumwater Canyon, ski on the 37 feet of snow that fall annually on Stevens Pass, or raft the Class IV Wenatchee River—all within half an hour of town—and you just might find yourself looking at real estate. And yodeling.

Charleston, South Carolina
Chucktown is affordable (median home price, $235,000) and small (pop. 110,000) but comes with the vitality of a metropolis, thanks to its kaleidoscopic heritage and a happening downtown. And since it sits at the confluence of the Cooper and Ashley rivers and the Atlantic Ocean, it's also prime watersport territory: There's sailing in the harbor, sea-kayaking through the marshes of the Intracoastal Waterway, and surfing at Folly Beach.

Alpine, Texas
At 4,481 feet, Alpine (pop. 4,800) avoids the smoldering heat of the West Texas lowlands and, partly thanks to the presence of Sul Ross State University, is home to a vibrant, thriving main street (think a kindergarten version of Austin's 6th Street). Davis Mountains State Park (30 minutes away) offers year-round camping and cycling, while Big Bend National Park, 90 miles southeast, offers some of the most rugged backcountry hiking and mountain biking in the country.

New London, Connecticut
As in the gritty port town known for the nearby submarine base? Well, yes. New London (pop. 25,923) is rebounding, with a surge in housing development on the Thames River and new restaurants, art galleries, and jazz bars near the waterfront. Home prices are a fraction of what you'll find in nearby Fairfield County, but the sailing on Long Island Sound is just as good.

Taos, New Mexico
Picture Colorado. Now remove most of the people; sprinkle with artists, hippies, eccentric ski bums, celebs, and the occasional nuclear scientist and you've got Taos (pop. 5,800). With the Class IV–V drops of the Rio Grande, a dozen fun little trout streams, and some of the country's most challenging in-bounds terrain (Taos Ski Valley) all within a quick drive, the access here rivals that of any Rocky Mountain town.

Ashland, Oregon
Ashland (pop. 23,000) is an anomaly: It's got the Northwest's first-rate recreation (you can bike or trail-run right from town in the surrounding Siskiyou Mountains, and the nearby kayaking is incredible) and culture (famous Shakespeare Festival)?but not the rain (196 days of sunshine annually). And with its Napa-style vineyards, this border town is a bit Cali—in a good way.