Chisholm Trail was a trail in the post-American Civil War era to drive cattle overland from ranches in Texas to Kansas railheads.

It may also refer to:

Roads Chisholm Trail Parkway in Texas

Cycleways Chisholm Trail (Cambridge), a walking and cycling route in Cambridge, England

Schools Chisholm Trail High School in Fort Worth, Texas Chisholm Trail Academy, co-educational high school in Keene, Texas

Games Chisholm Trail (video game), a computer game released in 1982

See also Chisholm (disambiguation)