Weatherford sits on the historic alignment of US Route 66, and the section through the town centre retains a number of mid-20th-century motels, diners, and signs that are characteristic of the road's mid-century heyday. The main interstate (I-40) bypasses the town to the south, leaving the old route relatively quiet and walkable.
For Route 66 travellers it is one of several worthwhile mid-Oklahoma stops alongside Clinton and Elk City, both nearby and home to dedicated Route 66 museums. Weatherford's own appeal is more in surviving streetscape than curated exhibits, although the Stafford Air and Space Museum just off the route is the area's main destination.