35. The Chilkoot Trail, Alaska (33 miles)Learn More
Of the 100,000 people who lit-out for the Klondike gold fields in the 1890s, less than 30,000 made it. Which speaks volumes about this tough, three-day trek through the Coast Mountains, once known as “the 33 meanest miles in the world” thanks to a series of deadly switchbacks and narrow traverses. Now part of a National Historic Park, the trail begins in the Alaskan ghost town of Dyea, slogs across several climatic zones— coastal rainforest, boreal forest, and high alpine range—and ends in Bennett, British Columbia, near the headwaters of the mighty Yukon River. Peak season is from June to August, and avalanche danger lingers into late May. Bear spray is a must.
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