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The crossing at Crazy Woman Creek represented a significant juncture in traveling the Bozeman Trail. The flat terraced bottoms above the creek afforded a desirable campspot to emigrant travelers. The campspot also provided the scene for one of the more dramatic White-Indian encounters along the trail. During the morning of July 20, 1866 an escorted wagon party of five wagons, two ambulances and four mounts under the command of Lt. James H. Bradley were ambushed by a substantial number of Indians. Attacked while the train was midstream, the military party beat a hasty retreat to a defensible position on the creek bank. Forming a circle configuration the party repelled repeated attacks, including one nearly successful attempt to use a nearby ravine to infiltrate the wagon corral. They remained under attack until a party was able to escape and obtain water from the nearby creek. Revived by the water the besieged group was able to hold out until a unit of 100 infantry approaching from Fort Carrington (later Ft. Phil Kearny) forced the Indian attackers to retreat. Two soldiers were lost and most of the detachment suffered wounds.

In 1876 the Crazy Woman Creek campsite again became the focus of military operations along the Bozeman route. The campaign under the command of General George Cooke encamped at the creek during the third of three major drives up the trail during that year. In this final drive against the Northern Plains tribes Colonel Ranald Mackenzie and his party of scouts and soldiers departed the Crazy Woman Creek camp to attack and destroy the major Cheyenne encampment in the Bighorn Mountains.