Prior to 2019, US 301 in Delaware started at the intersection of U.S. 40 and Delaware Route 896 in Glasgow. The highway was cosigned with DE 896, picking up Delaware Route 71 only three miles south of U.S. 40. Running parallel to US 13 and Delaware Route 1, the highway crossed the Chesapeake and Delaware Canal on the four-lane Summit Bridge. At Mount Pleasant, DE 896 headed east to intersect U.S. 13 at Boyd's Corner, while DE 71 continued to be cosigned with U.S. 301 until the road reached Middletown. U.S. 301 continued alone until it picked up two other roads, Delaware Route 15 and Delaware Route 299, which followed the highway to near the Maryland state line. On November 14, 2006, the Delaware Department of Transportation (DelDOT) announced that a new four-lane bypass around Middletown will reroute US 301 west of Middletown, with the road directly connecting to DE 1 in Biddles Corner. This bypass opened to traffic on January 10, 2019.