The Port of Entry at Grand Portage was established in 1964 when the International Bridge spanning the Pigeon River and connecting highways were completed.

[2] The first crossing was constructed from wood in 1916; which was replaced in 1930 by a steel truss bridge, which was paid-for jointly by the American and Canadian governments.

[3] Settlements developed at Outlaw bridge near the custom posts on both the Canadian and American sides of the Pigeon River.

These small towns contained hotels, gas stations and other businesses catering to travellers crossing the border.

Plans to move the crossing from Outlaw Bridge to a more direct route between Duluth and Port Arthur (now Thunder Bay) began as early as 1935 but efforts of the Minnesota government to acquire the necessary land for the roadway from the US government, which held it on behalf of the Chippewa tribe, proved challenging and ended up at the US Supreme Court in 1939.