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.