Chilkoot Trail

Chilkoot Trail, Alaska and Yukon Territory, U.S. and Canada

Skagway to Bennett Lake

Executive summary by darmansjah

Round-Trip: 33 miles, 3 to 5 days

When to Go: The Coast Range opens up a bit earlier than the Rockies, so you can push the season a bit. Late June to early October works most years, but August has the best weather—and sees the heaviest traffic.

The very names on this epic route—the Golden Stairs, the Scales, the Stone Crib—are redolent with the suffering of 1898 gold miners, and there’s no mistaking the history here. Both sides of the trail are littered with rusting remains of equipment the miners jettisoned out of exhaustion. More than a century later, the backcountry journey those miners blazed, driven by greed, has become one of the iconic wilderness routes in North America. It’s a natural. The route rises quickly from tidewater to crest Chilkoot Pass at 3,300 feet. But instead of dropping back down, it meanders more than 20 miles through an alpine wonderland, while losing only a thousand feet before returning to its terminus at Bennett Lake.

Insider Tip: Spanning two national parks, two countries, a state, a province and a territory, Chilkoot Trail makes staging a challenge. Solve that by starting and ending in Whitehorse, Yukon Territory, and use the robust infrastructure for trailhead transport. Take the White Pass and Yukon Railway over the mountains to Skagway, a stupendous ride, and have Alpine Aviation pick you up in a floatplane at Bennett Lake for the outrageous 45-minute flight back to Whitehorse, in plenty of time for a beer on the deck before dinner.

Chamonix, France

Best For: Adrenaline junkies who like their mountains big

Executive summary bydarmansjah

Globally renowned as the birthplace of extreme skiing (often defined as “you fall, you die”), Chamonixhas some of the world’s premier lift-accessed steep skiing and snowboarding—including plenty of terrain that won’t leave you dead on a glacier if you catch an edge wrong. Located in a deeply cleaved valley near the trisection of France, Italy, and Switzerland, the town sits in the shadow of the highest peak in the Alps, Mont Blanc, and a tangle of other glacier-clad mountains. Chamonix’s cobblestone streets and car-free pedestrian center make for a classic mountain village environment typically bustling with leathery mountaineers and gawking tourists. This is France, so the nightlife is predictably spirited, and diverse accommodations range from grimy climbers’ hostels to luxury lodgings.

But it’s the mountains that rule here. The many lifts and trams access terrain so steep and rugged that many skiers will be wishing for a ride down, as well. One ticket gains access to the 11 different ski zones scattered discontinuously across the valley. If the snow is good, vertical drops of over 9,000 feet are possible. With more glaciers—and their pesky offspring, crevasses—than any ski area in Europe, skiers and snowboarders who enjoy staying alive should hire a local guide before heading out of bounds.

Ask a Local 

Former France Ski Team member and current freeride world champion Aurélien Ducroz has lived his entire life in Chamonix. Here are his recommendations.

Best Digs 

Budget: The recently renovated Hotel du Louvre is in the center of town.

Swank: Le Hameau Albert 1er in downtown Chamonix is the only five-star hotel.

Best Eats 

Cheap: Maison Moustache et Filles, a new restaurant downtown, is run by Charles “the Moustache” and his two daughters, Maxime and Camille. It’s decorated with an extraordinary collection of old skis.

Gourmet: Le Cap Blanc, one of Le Cap Horn’s three venues, serves delicious sushi.

Best After-Ski Party Spot

Chambre Neuf, a Scandinavian-influenced bar, has live music and is host to the best after-ski vibe the town has had in years.

Best Rest-Day Activity 

Chamonix is a real city, so even if you’re not a skier there are many other things to do, such as visit the Alpine Museum.

Chamonix’s Classic Ski Run

La Vallée Blanche starts from the top of the Aiguille du Midi and goes for 16 kilometers on top of a glacier in the middle of incredible mountains!

Ketchum, Idaho

Best For: Hard-carving skiers and boarders who like playing “spot the movie star” 

Executive summary by darmansjah

The original Rocky Mountain ski resort, Ketchum’s Sun Valley featured the world’s first chairlift when it opened in 1936 and was long the stomping ground for classic-era Hollywood. The upscale mountain and its opulent lodges still carry the grandeur of their pre-war days while the old mining and sheep town of Ketchum, population 2,689, maintains a rustic elegance, with gourmet restaurants and steak-and-microbrew saloons in century-old brick buildings. The resort village of Sun Valley borders Ketchum at the base of Dollar Mountain, the original ski hill and now an ideal learner’s area with a ski school, terrain park, and separate, inexpensive lift tickets.

The main action for serious skiers and boarders is over at Bald Mountain, on the other side of town (free shuttle buses available), which features 3,400 vertical feet of some of the finest groomed plunges in the world. If you like never-ending, perfectly pitched corduroy, this is your mountain. Snowboarders will appreciate the mountain’s complete lack of flat areas, and abundant high-speed lifts means no one waits long in line. The resort’s proximity to exactly zero major population centers means the slopes are perpetually free of crowds, and top-to-bottom snowmaking means you’ll always have smooth groomers to carve. Don’t miss the luxurious Seattle Ridge Lodge atop Bald Mountain's Seattle Ridge, where mesmerizing views span the wild Pioneer and Sawtooth Mountains and the Woody River Valley below.

Ask a Local

Professional skier Reggie Crist has spent most of his life in Sun Valley. The former U.S. Ski Team member regularly appears in ski movies and is currently a consultant/athlete for Eddie Bauer/First Ascent and K2 Sports. Here are his recommendations.

Best Digs

Budget: Lift Tower Lodge

Swank: Sun Valley Lodge (this is where Hemingway worked on For Whom the Bell Tolls)

Best Eats

Cheap: Pioneer Saloon

Gourmet: Michel's Christiania

Best After-Ski Party Spot

Apples Bar and Grill

Best Rest-Day Activity

Visit Galena Lodge for lunch and drive to see the Sawtooth Mountains.

Sun Valley’s Classic Ski Run

Warm Springs—3,100 vertical feet of leg burn

Shoreline Highway

Shoreline Highway, Marin County, California

Executive summary by darmansjah

Shoreline Highway—Marin County’s winding, two-lane stretch of Highway 1 from Sausalito to the Sonoma County line—snakes through the Marin Headlands, hugs stunning coastal bluffs, and passes through Stinson Beach, a classic California beach community. Off-road mountain biking was born here—and on-road cyclists are ubiquitous—so take it slow, preferably in a hybrid vehicle to limit emissions and avoid running out of gas. Temps can be 10-to-15 degrees cooler than in nearby San Francisco, so bring a jacket, even on hot days. To enjoy the most expansive Pacific views, wait until the morning fog clears before making the drive north from the Golden Gate Bridge. Fuel up in Sausalito, and then stop at Muir Woods National Monument to walk among thousands of giant, old-growth redwoods. Before nightfall—since the scenic curves can be deadly in the dark—check-in at the Inn at Roundstone Farm, located within Point Reyes National Seashore. Spend a day exploring the seashore’s dramatic rocky headlands, 150 miles of hiking trails, and 2,600-acre tule elk reserve, where the fall rut (the late-summer to early-fall breeding season) inspires magnificent bull elks to bugle, battle, and butt antlers for affection.

Kalalau Trail, Kauai, Hawaii

Ke’e Beach to Kalalau Valley

Executive summary by darmansjah

Round-Trip: 22 miles, 3 to 5 days

When to Go: May to September for drier weather; April or October for more solitude

The finest coastal hike in the world, this rugged route through Kauai’s impressive Nā Pali Coast will challenge you physically with tropical heat and steep trails, and scare you with exposure on muddy slopes. But after a day of slogging 11 miles through the fluted cliffs above surf that crashes like howitzer fire on the coast below, you are rewarded with a view of the impossibly serene mile-long arc of golden Kalalau Beach along the shimmering Pacific. The Kalalau Valley itself holds fairy-tale waterfalls and lush tropical jungle, well worthy of exploration, but the highlight is camping right on the beach, with the Western Pacific before you, reflecting the setting sun.

Insider Tip: It’s hot, and you’ll be tempted, but don’t even think about cooling off with a swim at Hanakapi’ai Beach on the way in. All those small, makeshift memorials are erected in the memory of hikers who thought they might enjoy wading in and were immediately swept out to sea by the violent rips.