US 14 is mostly two-lane surface road with the exception of a few multilane urban arterials and a freeway section around Madison that it mostly shares with US 12.

[5] US 14 continues southeast into Richland County, bypassing Sylvan and Boaz before turning east.

After a seven-mile (11 km) east trek, the highway enters Richland Center and immediately turns south.

The two highways then head east-southeast to Lone Rock where they cross WIS 130 and exit to Sauk County.

[9] US 14 and US 12 follow the beltline south and around the west side of Madison and join US 18 east and US 151 north.

Highways head east for three miles (4.8 km) through urban Madison where US 151 splits north to head into downtown Madison and US 12 and US 18 continue east, while US 14 turns south toward Oregon on a seven-mile (11 km) stretch of freeway.

[9] US 14 turns southeastward at Evansville and passes through Leyden and then takes a northeastern bypass around Janesville, crossing US 51 and meeting up with I-39, I-90, and WIS 26 at a triangle formed by the three distinct routes northeast of the city.