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According to the United States Census Bureau, the town has a total area of 55.3 square miles, of which 55.0 square miles is land and 0.2 square miles (0.40%) is water. The west town line is the border of Erie County, New York, and the north town line is the border of Erie County and Genesee County.

The population was 3,349 during the 2000 census. The town was named after Bennington, Vermont. Geographically, the town of Bennington is the largest in Wyoming County, occupying a significant portion of the county's northwest corner.