Cloudcroft was established in 1898 when the El Paso-Northeastern Railroad crew laid out the route for the Cloud Climbing Railroad. The natural beauty and business possibilities for creating a getaway from the blistering summer heat in the valley below were obvious and plans were quickly made for a mountaintop resort. You can still see the Mexican Canyon trestle from this era as you drive NM 82 to the west of town. This incredibly steep, twisty, and scenic drive links Cloudcroft to the desert basin below and gains 4,700 feet in elevation during the steepest 16-mi stretch. Be sure to pull off the road and take a look.
One way this little mountain town promotes itself these days is with the slogan "9,000 feet above stress level," and from its perch high above the Tularosa desert valley the town lives up to the claim. Flowers and ponderosa and other greenery give the air an incredible mountain fragrance, and the boardwalks lining the main street, Burro Avenue, lend the town a kitschy Old West atmosphere that's a bit contrived, though still charming. Despite a significant influx of retirees and big-city expats over the past few years, the town has held onto its country friendliness.
There are two festivals that bookend the warm season here, and a number of others in between. Mayfest happens over Memorial Day and Aspencade is held the first weekend of October. The July Jamboree, and a Labor Day weekend fiesta are two more events held, along with street dances and the melodramas that most of the residents seem to participate in. Festivals typically include arts-and-crafts booths and all sorts of calorie-laden munchies.
Cloudcroft has the southernmost ski area in the United States, although it's a very small operation and only open during years when snow is abundant (snowfall is about 90 inches a year on average). It's a nice place for beginner skiers to get their snow legs. Contact the Chamber of Commerce for season info and ticket prices.
It is well worth getting off the boardwalks of the main village and getting into the forest to explore the countless trails and canyons, either on foot or on a mountain bike. There are trails for every level of fitness—don't miss having a hike in the clean, cool mountain air before you head back down to the heat below.