Montgomery was first settled in 1767 and was officially incorporated in 1780. The town was named after General Richard Montgomery, who died in the Battle of Quebec. It took land from Westfield, Southampton, and unincorporated land that is now Huntington. A small town, it grew bigger when Interstate 90 was built in 1957 and has served as an outer commuter town to Springfield.

According to the United States Census Bureau, the town has a total area of 15.2 square miles (39 km²), of which 15.1 square miles (39 km²) is land and 0.1 square miles (0.26 km²) (0.86%) is water. Montgomery is bordered by Southampton to the northeast, Westfield to the southeast, Russell to the southwest, and Huntington to the northwest. Its border with the towns of Huntington and Southampton make up a portion of the Hampden-Hampshire county border. The center of Montgomery lies 17 miles (27 km) west-northwest of Springfield and 101 miles (163 km) west of Boston. Thus, like most of Western Massachusetts, it is closer to two other states' capitals - Hartford and Albany - than its own.

The town of Montgomery lies atop a high plain, reaching into neighboring Huntington, framed by Lizzie Mountain to the northeast and Tekoa and Shatterack Mountains to the south and west, respectively. The latter two mountains rise from the banks of the Westfield River, whose banks make up a portion of the town's border with Russell. Within the town, the Moose Meadow Brook runs from north to south, with the Westfield Reservoir atop the plain and the smaller Tekoa Reservoir near the bottom of the slope of its namesake mountain. Several other small brooks run through the town.

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