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Roundup is an incorporated city and the county seat of Musselshell County in central Montana.

The city takes its name from the cattle roundups that ranchers held along the Musselshell River in the 1880s.

A first settlement called Roundup was founded in 1882 by buffalo hunter James McMillan at the meeting of Half Breed Creek and the Musselshell River, and a post office opened in 1883.

Roundup was effectively founded a second time after the Milwaukee Road railroad arrived in 1907 and coal mines opened in the Bull Mountains; the town grew up a short distance north of the original site and incorporated in 1909.

The 2020 census counted 1,742 residents in Roundup, living in 778 households, with 937 housing units in the city.

Roundup's population peaked at 2,856 in the 1950 census, during the height of the local coal era.

The Musselshell River forms Roundup's southern border, with the Bull Mountains rising beyond it, and U.S. Routes 12 and 87 cross in the city, about 49 miles north of Billings.

Roundup was the starting point of the Great Montana Centennial Cattle Drive of 1989, and cattle drives are still held from the city annually.

The Musselshell Valley Historical Museum in Roundup recreates frontier-era settings such as a hospital, a general store, and a school, and displays a coal exhibit largely funded by Signal Peak Energy.

Coal mining in the Bull Mountains and agriculture anchor Roundup's economy, and the city has also become a hub for Amazon prep-center businesses that pack goods for the company's warehouses.