Prior to official settlement, the area of Monterey was inhabited by Mahicans, the local Native American tribe. Monterey was first settled by colonists in 1739 as a part of Housatonic Township Number One. The township had two villages, along Hop Brook to the north (modern Tyringham) and Konkapot River in the south (modern Monterey). The town was officially incorporated as Tyringham in 1767. In the earliest days of 1776, General Henry Knox passed through the town, bringing cannons from Fort Ticonderoga in New York to aid in ending the Siege of Boston. Today, the path he took is known as the Henry Knox Trail. However, the long divide between the two towns led to their separation in 1847. Previously called Green Woods or South Tyringham, the local people voted to name the new town Monterey to commemorate the Battle of Monterey that took place a year earlier in the Mexican–American War. Palo Alto and Buena Vista were also considered, but thought to be "too foreign sounding". The town was mostly known for its sawmills, but today it is a rural community, known more for its recreational areas in the state forests and along Lake Garfield.

According to the United States Census Bureau, the town has a total area of 27.4 square miles (71.0 km²), of which 26.4 square miles (68.5 km²) is land and 0.97 square miles (2.5 km²), or 3.53%, is water. Monterey is bordered by Tyringham to the north, Otis to the east, Sandisfield to the southeast, New Marlborough to the south, and Great Barrington to the west. Monterey lies 21 miles (34 km) south-southeast of Pittsfield, 37 miles (60 km) west of Springfield, and 124 miles (200 km) west of Boston.

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