U.S. Federal Route 302 is one of the main east-west highways across Cumberland County. It runs from the Cumberland/Oxford County Line, near Fryebrug, to Interstate 295/U.S. Rt. 1/Maine State Route 77, at Portland. U.S. Rt. 302 passes through the following towns in Cumberland County. Bridgton Naples Casco Raymond Windham Westbrook Portland U.S. Rt. 302 is multi-plexed in Cumberland County. Maine State Route 117, at Bridgton. Maine State Route 11, at Naples. Maine State Route 35, from Naples to Windham.