In 1902, this Sonoran Desert town was the copper-mining king of the West. Today, Bisbee (pop. 6,300) is more like a sun-baked Telluride on acid, where cycling is the sport of choice. Sitting eight miles north of Mexico and just east of the Mule Mountains, Bisbee attracts writers, artists, and world-class chefs who live in renovated mining shacks and ride their fixed-gears to the St. Elmo bar on Brewery Avenue. (According to local legend, the dive was once a hangout for the Monkey Wrench Gang.) From January through April, temps hover in the fifties, meaning you can cycle on quiet, mesquite-lined roads in comfort. Rent a bike on the way down from Tucson in Sierra Vista, at Sun 'N' Spokes ($40 per day for expert-level bikes; sunnspokes.com), and crash in Bisbee at the 126-year-old Letson Loft Hotel (doubles from $115; letsonlofthotel.com). Then set out for daylong forays like the 23-mile Lavender Pit ride. Ask for directions at the Bisbee Bicycle Brothel, a mini-museum of vintage and modern rides (bisbeebicyclebrothel.com). NEAREST AIRPORT: Tucson, two hours.
Winter Escape: The Berkshires
Thanks to plenty of art galleries and theater troupes, plus what may be the nation's highest number of prep schools per capita, the Berkshires aren't often accused of being wild. But these old highlands have secrets, and they're best found in winter. Base yourself in Charlemont, at the Warfield House Inn (doubles from $112; warfieldhouseinn.com), a farmhouse set on 530 acres and overlooking Mohawk Trail State Forest. Rent snowshoes or cross-country skis in nearby Adams, at Berkshire Outfitters (from $25 per day; berkshireoutfitters.com), and get trail info from the Appalachian Mountain Club (amcberkshire.org). Then explore Mount Greylock State Reservation's 70 miles of trails, including the Appalachian. For a workout with a payoff, skin 90 minutes up Greylock on the Thunderbolt Trail, a ski-racing route built in the thirties, then come down in a hurry. (Bring your own alpine-touring setup or rent downhill skis at Ski Fanatics, in Lanesborough, 413-443-3023, and snowshoe up.) Day two: Head 20 minutes to North Adams for some sculpture browsing at the excellent Massachusetts Museum of Contemporary Art ($15; massmoca.org). Hey, it's the Berkshires! NEAREST AIRPORT: Albany, 90 minutes, or Boston, three hours.
Winter Escape: Quebec City
Instead of splurging on Europe, try Quebecyou get all the nightlife, plus Canadian wilderness, at a fraction of the price. Base yourself in medieval-style Quebec Cityjust a 90-minute flight from Newark on Continentalat Auberge Saint-Antoine, an old wharf warehouse turned boutique hotel (doubles, US$150; saint-antoine.com). On night one, wander along 17th-century ramparts, then jump into Old Town and shake it at the Maurice nightclub. The next day, drive 40 minutes northeast to the hamlet of Sainte-Anne-de-Beaupré to ski Mont Sainte Anne's 200-plus miles of groomed cross-country tracks and 65 downhill trails (lift tickets, US$58; nordic passes, US$19; rentals from US$36; mont-sainte-anne.com). The spruce-lined routes offer views of Quebec City jutting up beside the St. Lawrence River. Buyer beware: Quebec City's Winter Carnival runs January 29February 14, so you may notice 800,000 others drinking among outsize ice sculptures and watching 48 teams of paddlers sprint across the half-frozen St. Lawrence during the Ice Canoe Race. NEAREST AIRPORT: Quebec City, 20 minutes.
Winter Escape: Lutsen Mountains
Secret tree stashes? A hairy double-black-diamond chute? Terrain and powder that feel more West than East yet lie in the heart of the country? Lutsen, mid-America's largest ski resort, has them all. But it's still the Midwest (vert: 1,088 feet), so come for more than the downhill. Four hours from Minneapolis on Minnesota's North Shore, Lutsen abuts boreal forests offering every winter activity, from snowshoeing to sleigh rides. Stay at the Lutsen Resort (doubles from $69; lutsenresort.com), on the shores of Lake Superior. The lodge will set you up with a complimentary set of cross-country skisthey'll even guide you for freeand you'll be able to access nearly 100 miles of nordic trails in the surrounding Sawtooth Mountains. Or get your mush on with Grand Maraisbased Sled Dog Adventures, which runs daylong courses with nearly 100 Alaskan huskies (from $100; dogmushing.com). Then there's the ski resort itself, which offers 1,000 acres of terrain. Cap it all off with a Grain Belt Premium at Papa Charlie's Tavern and Stage, a classic Northwoods pub at the base of the mountain, where you can rock a flannel shirt and wool cap sans irony. NEAREST AIRPORT: Duluth, Minnesota, two hours.
Winter Escape: Rocky Mountain National Park
Yes, nearly three million people visit Rocky Mountain National Park each year. But most of them come in the warmer months, leaving the park's 12,000-to-14,000-foot peaks emptyand open to backcountry skiers all winter. No experience? No problem. Sign up with Estes Parkbased Colorado Mountain School, which offers daylong introductory courses ($170; totalclimbing.com). Backcountry veterans, pick up a copy of Front Range Descents: Spring and Summer Skiing and Snowboarding in Colorado's Front Range ($20; neptunemountaineering.com) and aim for the Ptarmigan Fingers area of Flattop Mountain. The three-mile approach is mellow, and there are lappable, north-facing couloirs and bowls of varying difficulty, making it the ideal first tour to assess snow stability. Lodging: For $25 you can reserve a bunk at CMS's hostel-like base camp, which completes the dirtbag hat trick with a full kitchen and occasional screenings of old ski movies. Those wanting less fragrant digs should check out the Sunnyside Knoll Resort (from $75; sunnysideknoll.com), an unpretentious joint just outside the main entrance to the park with a couple of hot tubs overlooking the Fall River. NEAREST AIRPORT: Denver, 90 minutes.
Winter Escape: Big Pine Key
Scouting your Florida Keys playground
An important lesson my grandfather Herb taught me: Sun and sand are good, but they're even better when you add bistec de Palomilla and stone crab. The best spot to enjoy this combo stateside is the Florida Keys, and if you head for Big Pine Key, you can mix in some adventure while dodging the notorious local schlock. First, make a beeline for the Deer Run Bed & Breakfast (from $225; deerrunfloridabb.com). The eco-minded inn serves delicious vegan breakfasts (hey, Herb liked veggies, too) and provides kayaks on its Atlantic-facing beach. When you're ready for serious paddle exploration, mosey seven miles north to Big Pine Kayak Adventures (keyskayaktours.com). Owner Bill Keogh literally wrote the book on kayaking here2004's Florida Keys Paddling Guide ($18; countrymanpress.com)and offers four-hour tours winding around wild mangrove islands ($125 per person). Saturday night is for bistec, and I promise the 45-minute drive to Key West will be forgotten the moment you smell the Cuban food at El Siboney (elsiboneyrestaurant.com). The next morning, snorkel the shallow reefs of Looe Key Marine Sanctuary with Strike Zone Charters ($35 per person; strikezonecharter.com), which launches catamaran-based trips ten minutes from Deer Run. On your drive back to the mainland, complete Herb's recipe with fresh stone crab at the Keys Fisheries Restaurant (keysfisheries.com), on Marathon Key. NEAREST AIRPORT: Fort Lauderdale or Miami, three hours.
Winter Escape: Joshua Tree National Park
You can find otherworldly landscapes all over the Southwest, but few are easier to reach than Joshua Treejust an hour from Palm Springs or two and change from L.A. The park is named for its Seussian forests of hydra-headed yucca, but the real attraction is the rocks. The best way to appreciate the monolithic eggs and 747-size mounds of boulders is with your hands. The trad climbing on J-Tree's tacky granite is legendary. Beginners will want to take a course from the Joshua Tree Rock Climbing School (from $125; joshuatreerockclimbing.com). With midwinter highs in the sixties, though, it's easy to spend a weekend exploring whatever spot you choose. If you're sticking by the car, shoot for one of the smaller campgrounds (Ryan, Belle, and White Tank), around scramble-friendly rock gardens. Or head off-trail, into the labyrinthine backcountrysay, in the Wonderland of Rocks, around Willow Holethen follow your waypoints back. Lodging: Good options are scant, so book a month early to snag one of the two rooms with saltwater hot tubs at the new Sacred Sands B&B, in the town of Joshua Tree (doubles from $269, two-night minimum; sacredsands.com). NEAREST AIRPORT: Palm Springs, 45 minutes.
Winter Escape: Sundance Strategy
The Sundance Film Festival, which takes place January 2131 in Park City, Utah, is ten days of mayhem that, if you're not in the industry, is best skipped. Those who attend have to fight for lodging, go dizzy sifting through the available screenings, stand in long, cold lines, and endure the gaggle of star gazers on Main Street. Our advice? Go native. Immediately following the festival, the Sundance Institute screens the award-winning films for the locals. Tickets for Best of Fest are free on a first-come, first-served basis at the main box offices in Park City, Salt Lake City, Sundance resort, and Ogden on January 16 and 17. Early birds can grab four tickets, so call a buddy in Utah and have him score you a pass. High-rollers: Crash at the brand-new Dakota Mountain Lodge, the first Waldorf property in a ski town (doubles, $350; dakotamountainlodge.com). For more affordable digs, try the Carriage House (doubles, $115; allseasonsresortlodging.com). Before the screenings begin, you'll want to get into some powder. From the top of Park City's McConkey's lift, traverse skier's left to the Black Forest, a north-facing glade that often gets overlooked.