1. Telluride, Colo.: This National Historic Landmark district, tucked within a box canyon and protected by towering, 14,000-foot peaks, provides a breathtaking setting for a family getaway any time of year. Top-ranked alpine skiing gives way to fly-fishing, hiking and biking amid wildflowers come summer. It’s also a cultural haven, with year-round festivals celebrating film, music and art. A free gondola connects the historic town with the more modern Mountain Village. At 9,500 feet, the enclave is home to the Telluride Ski Resort. Contact: visittelluride.com.
2. Sisters, Ore.: In Central Oregon, you’ll find a comfortable combination of outdoor adventure, chic restaurants and a hip art and music scene. Named for a nearby trio of peaks, the truck stop turned trendy small town offers year-round family-friendly activities including fishing derbies, quilt shows, rafting, skiing, hiking and boating. Contact: (800) 547-7842; traveloregon.com.
3. Red Lodge, Mont.: Sample authentic Western hospitality when you spend time in this historic community best known as a gateway to Yellowstone National Park. Set out for the spectacular Beartooth Highway, a winding, cliff-hugging 68-mile stretch that delivers on its promise to provide some of the most stunning vistas in America. In addition to several local galleries, the town hosts a skijouring competition in winter and pig races during the summer. Contact: (406) 446-4402; redlodge.com.
4. Cody, Wyo.: Summer means nightly calf-roping and bronc-riding at this small town’s popular rodeo. Offering outdoor adventures including hiking, biking, horseback riding and blue-ribbon trout fishing, Cody is also home to the Buffalo Bill Historical Center, where five museums provide plenty to interest every family member. Spend the night at the Irma, a colorful inn on the main drag, built by Buffalo Bill himself and named for his daughter. Contact: (800) 393-2639; yellowstonecountry.org.
5. Williams, Ariz.: Named after “Old Bill” Williams, a trapper, trader and mountain man, this Arizona town just west of Flagstaff is proud of what locals say is the best preserved stretch of Route 66. Visit Bearazona, a local wildlife park, before hopping aboard the vintage Grand Canyon Railway train for a trip to the south rim of the Grand Canyon. Choose from several classes of service and various packages, some of which include a night’s stay within the Grand Canyon National Park before returning to Williams. Contact: thetrain.com; experiencewilliams.com.