Middlebury is located at 44°0'55" North, 73°10'4" West (44.015278, -73.167778).
According to the United States Census Bureau, the town has a total area of 14.05 mi2 (36.40 km2). 13.93 mi2 (36.09 km2) of it is land and 0.12 mi2 (0.31 km2) of it is covered by water. The total area is 0.85% water.
Middlebury is located in the Eastern Standard Time (EST) timezone, GMT-05:00. It observes Daylight Saving Time (DST).