According to the United States Census Bureau, the town has a total area of 23.7 sq mi (61.3 km²), of which 22.7 sq mi (58.9 km²) is land and 0.93 sq mi (2.4 km²), or 3.97%, is water.
Stockbridge is bordered by Richmond to the northwest, Lenox to the north and northeast, Lee to the east, Great Barrington to the south, and West Stockbridge to the west.
The town is located 13.5 miles (21.7 km) south of Pittsfield, 35 miles (56 km) southeast of Albany, New York, 45 miles (72 km) west-northwest of Springfield, and 130 miles (210 km) west of Boston.

Set among the Berkshire Mountains, Stockbridge is drained by the Housatonic River, which runs through the center of town.
The river is fed by several marshy brooks and lakes, including Mohawk Lake to the west, Agawam Lake to the south, Lake Averic in the northwest, and Lake Mahkeenac, also known as the Stockbridge Bowl, to the north.
Stockbridge Bowl is the site of a town beach, a boating club, and a summer camp, Camp Mah-Kee-Nac.
North of the bowl lies parts of Tanglewood.
To either side of the bowl lie West Stockbridge Mountain and Rattlesnake Hill.
To the south, Monument Mountain peaks on the Great Barrington town line, and Beartown Mountain peaks to the east, closer to the Lee town line.

The town is nearly bisected by Interstate 90, the Massachusetts Turnpike.
There are exits in neighboring West Stockbridge and Lee.
Several state routes, including Route 102, Route 183 and U.S. Route 7 all pass through town, with Routes 102 and 7 sharing a short stretch in downtown Stockbridge, and Routes 102 and 183 meeting in the village of Larrywaug.
In this village are the Berkshire Botanical Gardens and the Norman Rockwell Museum.
South of there, in the village of Glendale, Massachusetts lies Chesterwood.

The Housatonic Railroad, the main rail line between Pittsfield and Great Barrington, passes through the town and lies mostly on the southern bank of the river.
The town lies along a Berkshire Regional Transit Authority (BRTA) bus line, which provides service between Pittsfield and Great Barrington.
Pittsfield is also the site of the nearest regional bus service, as well as regional Amtrak service.
There are local airports in Pittsfield and Great Barrington, and the nearest national air service is located at Albany International Airport in New York.
According to the United States Census Bureau, the town has a total area of 23.7 sq mi (61.3 km²), of which 22.7 sq mi (58.9 km²) is land and 0.93 sq mi (2.4 km²), or 3.97%, is water. Stockbridge is bordered by Richmond to the northwest, Lenox to the north and northeast, Lee to the east, Great Barrington to the south, and West Stockbridge to the west. The town is located 13.5 miles (21.7 km) south of Pittsfield, 35 miles (56 km) southeast of Albany, New York, 45 miles (72 km) west-northwest of Springfield, and 130 miles (210 km) west of Boston.
Set among the Berkshire Mountains, Stockbridge is drained by the Housatonic River, which runs through the center of town. The river is fed by several marshy brooks and lakes, including Mohawk Lake to the west, Agawam Lake to the south, Lake Averic in the northwest, and Lake Mahkeenac, also known as the Stockbridge Bowl, to the north. Stockbridge Bowl is the site of a town beach, a boating club, and a summer camp, Camp Mah-Kee-Nac. North of the bowl lies parts of Tanglewood. To either side of the bowl lie West Stockbridge Mountain and Rattlesnake Hill. To the south, Monument Mountain peaks on the Great Barrington town line, and Beartown Mountain peaks to the east, closer to the Lee town line.
The town is nearly bisected by Interstate 90, the Massachusetts Turnpike. There are exits in neighboring West Stockbridge and Lee. Several state routes, including Route 102, Route 183 and U.S. Route 7 all pass through town, with Routes 102 and 7 sharing a short stretch in downtown Stockbridge, and Routes 102 and 183 meeting in the village of Larrywaug. In this village are the Berkshire Botanical Gardens and the Norman Rockwell Museum. South of there, in the village of Glendale, Massachusetts lies Chesterwood.
The Housatonic Railroad, the main rail line between Pittsfield and Great Barrington, passes through the town and lies mostly on the southern bank of the river. The town lies along a Berkshire Regional Transit Authority (BRTA) bus line, which provides service between Pittsfield and Great Barrington. Pittsfield is also the site of the nearest regional bus service, as well as regional Amtrak service. There are local airports in Pittsfield and Great Barrington, and the nearest national air service is located at Albany International Airport in New York.
Stockbridge, Massachusetts