The height of land of the pass is located in Addison County.

On the southeast side of the height of land, the notch is drained by the Robbins Branch, thence into the Hancock Branch of the White River, which drains into the Connecticut River, and into Long Island Sound in Connecticut.

To the northwest, the notch is the source of the South Branch of the Middlebury River, which drains into Otter Creek, and into Lake Champlain.

The Long Trail, a 272-mile (438-km) hiking trail running the length of Vermont, crosses Middlebury Gap between 3,234-foot (986 m) Worth Mountain, 2 mi (3 km) to the south, and 3,323-foot (1,013 m) Boyce Mountain, 2.5 mi (4 km) to the north.

The Middlebury College Snow Bowl is just south of the gap, and beyond that is the Joseph Battell Wilderness.