GPS: 45°11'N 109°15'W
Set beside Yellowstone National Park in the wooded Beartooth Mountain foothills, Red Lodge is the toned-down alternative to Jackson—complete with a smaller (and less intimidating) ski resort on its 9,416-foot (2,870-meter) signature peak. The town’s epic 71-mile (117-kilometer) Peaks to Prairie Adventure Race triathlon every April shows outsiders what they’re missing.
Beartooth Mountain Guides offer beginner and multi-pitch ice climbing courses through some remote mountain passes ($225 a day, including all gear;http://www.beartoothguides.com/). Hike the Silver Run Plateau Trail up a conifer-forested canyon for the best skyline views of glaciers, alpine lakes, and snowcapped peaks from 10,000 feet (3,048 meters) above.
Warm up at the Red Lodge Ales Brewing Company, which serves fresh, award-winning beers like the Bent Nail I.P.A., a tribute to the town's contractors (www.redlodgeales.com). And at the Bear Creek Saloon & Steakhouse, you can bet on pig races while eating a charbroiled steak (+1 406 446 3481).
Base yourself at The Pollard, where Buffalo Bill Cody and Calamity Jane used to saddle-up (doubles from $145; www.thepollard.com).