It begins at the Connecticut state line in Sheffield and ends at U.S. Route 20 (US 20) in Pittsfield.

It heads mostly northbound, east of Mount Everett and the southern Taconic mountain range.

In neighboring Egremont, the road becomes concurrent with Route 23, turning northeastward into Great Barrington.

Route 41 heads relatively northward into West Stockbridge, where it meets exit 3 of the Massachusetts Turnpike.

In Richmond, it meets the end of Route 295, which leads shortly into New York.