The Chilkoot Trail is a trail in the Chilkoot mountains in Alaska that leads from Dyea, Alaska, United States to Bennett, British Columbia, Canada through the Chilkoot Pass in the Coast Mountains. The trail was long used by the Tlingit as a trade route and was used in 1897 - 1899 by gold prospectors who disembarked at Dyea and crossed into Canada in order to reach the Klondike gold fields.

The modern Chilkoot Trail begins at the Taiya River bridge near the Dyea townsite and follows the river into the Chilkoot pass, then runs through the Chilkoot Pass to Bennett, British Columbia, on Lake Bennett, a distance of about 53 km (33 miles). It is part of the Klondike Gold Rush National Historic Park on both the United States and Canada sides of the border. From Dyea, the trail ascends at a steep angle from sea level to 3,550 feet from Dyea and then descends to Lake Bennett. The hike usually takes three days now, but the Gold Rush prospectors, who were required by the Canadian government to bring 900 kg (1 ton) of goods, took 40 days to reach Lake Bennett.

The name Chilkoot comes from the name of the Tlingit group that used the trail for commerce.