Lay of the Land
Downtown Aspen is like a tiny Manhattan, designed on a grid. You cannot get lost for long. From Main Street, everything is within walking distance—hotels, restaurants, playgrounds, Carl's Pharmacy, trailheads, the Music Festival tent, the Aspen Center for Environmental Studies, and the historic West End, a neighborhood of brightly colored Victorian houses. On the south side of town, there's Aspen Mountain, a.k.a. Ajax, its chartreuse slopes contrasting with the dark green forest. (For a gorgeous view, and lunch at the Sun Deck restaurant, you can take the gondola to the top year-round.) On the north side of town, there's Red Mountain, a steep hill covered with 20,000-square-foot mansions belonging to business tycoons like Jeff Bezos of Amazon.com and Leslie Wexner of the Limited stores (note the outbuildings for housing wine and art collections—and staff). For a more hip and humble environment, follow Route 82 out of town to the ex-mining communities of Basalt, El Jebel, and Carbondale. They're where the regular people live.
The elevation of Aspen is 8,000-plus feet, and being up that high can do weird things to you. Beware of strange dreams, and sometimes even headaches and chest pains, on your first night. Drink lots of water, eat fruit, and lay low at the start.
The Aspen Idea
TAKE YOUR DAILY HIKE Two of my family's favorite walks are the Braille Trail, an aromatic 1.25-mile roped loop designed for blind trekkers (we close our eyes or squint as we go), and the Grottoes, home to ice caves, barreling waterfalls, and a campground (we haven't yet spent the night, but we've built campfires in the daytime). Get outfitted at the UTE Mountaineer, which has maps, nutrition bars, hiking shoes, and the crucial book, Aspen Snowmass Trails: A Hiking Trail Guide, by Warren Ohlrich. 308 S. Mill St.; 970/925-2849; www.utemountaineer.com.
GO BIKING The town's bike paths are incredibly extensive—you can ride to church; to the Aspen Recreation Center; to the nearby town of Snowmass, which has more mountain biking on the ski slopes; even to the airport. For rentals, go to Ajax Bike & Sport (635 Hyman St.; 970/925-7662; www.ajaxbikeandsport.com), where the staff all have shaved heads—better aerodynamics. The most family-friendly outing is on the Rio Grande Trail. Paved, and wide enough for tricyclists, Burleys, and tandem bikes, it follows the Roaring Fork River from Aspen's West End to Woody Creek, a neighborhood six miles away, and beyond. Stop for burgers, burritos, and Shirley Temples at the Woody Creek Tavern, where Hunter S. Thompson and his shotgun once hung out. 2 Woody Creek Plaza; 970/923-4585; lunch for four $35.