SR 166 begins at an intersection with US 17 just north of the Dominion Boulevard Steel Bridge over the Southern Branch Elizabeth River in the independent city of Chesapeake. The state highway heads north as Bainbridge Boulevard, a two-lane road that parallels the river through an industrial area. SR 166 passes under Interstate 64 with no access, meets the western end of SR 190, and crosses Newton Creek. The state highway has a partial cloverleaf interchange with US 13 and US 460 ; within the interchange, SR 166 descends to pass under Military Highway and Norfolk Southern Railway's Norfolk District. SR 166 heads north concurrent with US 460. The highways pass under I-464 and cross Milldam Creek, and continues north as a four-lane undivided highway into the South Norfolk area of Chesapeake. SR 166 and US 460 pass under another Norfolk Southern rail line and meet SR 337 at the junction of Bainbridge Boulevard and Poindexter Street. SR 337 heads north on Bainbridge Boulevard and west on Poindexter Street toward an interchange with I-464 and the Jordan Bridge across the Southern Branch Elizabeth River to Portsmouth; SR 166 and US 460 head northeast on two-lane Poindexter Avenue. At SR 246, the two highways turn west for one block before continuing northeast on four-lane 22nd Street, which crosses over the Norfolk District rail line and another rail line. SR 166 and US 460 veer onto two-lane Wilson Road at Berkley Street, where the road enters the city of Norfolk. SR 166 and US 460 expand to a four-lane divided highway just south of Indian River Road, north of which the highways meet SR 168 at an acute intersection that does not allow access from northbound SR 168 to southbound SR 166. SR 166, US 460, and SR 168 head north as a six-lane divided highway across the Eastern Branch Elizabeth River on the Campostella Bridge. The boulevard's name changes from Campostella Road to Brambleton Avenue at its partial cloverleaf interchange with I-264. There is no access from eastbound I-264 to northbound SR 166 or to westbound I-264 from either direction of SR 166. Just north of the interchange, the three highways pass under the Tide Light Rail next to the NSU station and SR 166 turns northeast onto Park Avenue while US 460 and SR 168 continue northwest toward Downtown Norfolk. SR 166 follows the four-lane divided street along the western edge of the Norfolk State University campus and intersects US 58 before turning onto four-lane undivided Princess Anne Road, which heads west as SR 404. SR 168 has a grade crossing of Norfolk Southern's rail line to Sewell's Point and expands to a divided highway as it passes along the northern edge of an industrial area, where the highway meets the southern end of SR 194. SR 166 follows Princess Anne Road to its eastern end at Military Highway, which is US 13 heading south and SR 165 heading north. The three highways continue east on six-lane Northampton Boulevard. At the next intersection, SR 165 splits south onto Kempsville Road. SR 166 and US 13 continue east across Lake Wright and meet I-64 at a partial cloverleaf interchange. The interchange includes a flyover ramp from southbound SR 166 to eastbound I-64 but does not include ramps from northbound SR 166 to westbound I-64 or from eastbound I-64 to southbound SR 166; those movements are made via Military Highway to the north. SR 166 and US 13 enter the city of Virginia Beach at Wesleyan Drive, which leads south to Virginia Wesleyan College. SR 166 diverges from US 13, which continues to the Chesapeake Bay Bridge-Tunnel, onto Diamond Springs Road. The state highway follows that four-lane divided highway north between an industrial area and a residential area to its northern terminus at US 60 adjacent to Naval Amphibious Base Little Creek.
