Dodgetown was named after its founding settler, Asahel Dodge, who immigrated to the area from Cape Cod.

Abundant streams and rivers provided water power for mills that produced textiles and wire.

Papermaking became the principal industry in 1806 with the construction of the Willow Mill by Samuel Church in South Lee.

The Columbia Mill in central Lee was established in 1827, and eventually became the first to supply 100% groundwood newsprint to The New York Times.

[6] Lee has become a popular tourist destination, noted both for its New England charm and its bed and breakfast establishments.

[7] Arlo Guthrie's court appearance before the blind judge and his seeing-eye dog for dumping garbage as described in the song "Alice's Restaurant" took place in the courtroom at the Lee Town Hall.

[8] Lee is bordered by Lenox to the northwest, Washington to the northeast, Becket to the east, Tyringham in the southeast, Great Barrington to the southwest, and Stockbridge to the west.

In the southwestern corner of town lies a portion of Beartown State Forest, where Burgoyne Pass crosses the northern end of the mountain.

The Appalachian Trail skirts the eastern part of town, passing through Tyringham, Becket and Washington.

Lee lies along the Housatonic Railroad line, which travels from Pittsfield to Great Barrington and Sheffield, terminating near at New Milford, Connecticut, near Danbury.

As of 2013 negotiations are underway to restore rail commuter service between the Berkshires and New York City along this route.

The town is covered by the Berkshire Regional Transit Authority (BRTA) bus line, which runs between Pittsfield and Great Barrington.

Regional bus services make regular daily stops, and maintain year-round schedules through Lee.

Peter Pan and Bonanza Bus Lines each make scheduled stops at Town Hall.

Bradley International Airport, near Hartford, Connecticut, approximately 70 miles (110 km) from Lee, is also a popular option.

Goose Pond and Laurel Lake are two significant bodies of water located in Lee, Massachusetts.

[26] It is a glacially formed body of water that is long and narrow, stretching over two miles in length but only a quarter-mile at its widest point.

The town of Tyringham maintains a boat ramp close by, which serves as the only public access point.

[29] In another incident, a fugitive from Maine was found hiding in the hikers' shelter near Goose Pond after fleeing from a car accident on Route 90.

[31] Laurel Lake has been facing challenges with invasive species, particularly Eurasian watermilfoil and zebra mussels.

The Laurel Lake Association, in partnership with the Town of Lee, has been actively involved in the prevention and management of these invasive species.