Plentywood is located in the Northeast corner of the state and has served as a trading post for the people living in that part of the state. The people have much tenacity and have experienced a repeating cycle of prosperity, drought, and starvation. Recently the economy was boosted by oil exploration.
At the site of present-day Plentywood, Sitting Bull and his Sioux people surrendered to the U. S. Army after living in Canada for five years. The Outlaw Trail crossed into Canada north of Plentywood. Rustlers moved their stolen cattle and horses along this passage across the border. Butch Cassidy named the trail and established a rest station in the Big Muddy Valley, west of Plentywood. At the turn of the century, the gulches around Plentywood harbored every manner of outlaw. This area was 'the Old West' legend. This small yet lively town features exotic animal farm tours and a hot air balloon rally in June. The Sheridan County Museum features the state's longest interior mural, depicting the history of the county.