A sizeable portion of the road runs in close proximity to the east side of Holmes Creek.

State Road 277 begins at State Road 79 in Vernon, both of which were undergoing a major reconstruction project in the early 2010s that led to the relocation of the south end of SR 277 onto Court Avenue near the vicinity of Church Street.

As with much of the Florida panhandle, the surroundings along SR 277 are primarily rural and agricultural, but is still part of the city, as evidenced by where it passes by Vernon Fire Department.

After crossing a power line right-of-way, the road intersects a local paved street running northwest named Culpepper Lane, a street which leads to the Big Pine Lake Boat Launch park on Holmes Creek.

The surrounding farmland ends temporarily just south of a culvert over a creek, replaced by forestland.

The route begins at US 90 east of the eastern terminus of SR 277 as Griffin Road west of the Chipley border.

CRs 166/277 make a reverse curve to the north and back to the west again over a bridge over Alligator Creek, a tributary of Holmes Creek, then CR 277 turns north again at Cope Road, while CR 166 continues west towards the Washington-Holmes County Line where it becomes an unmarked road leading to the city that bears its name.

CRs 162/277 runs straight north at first, but then curves more toward the northeast at the intersections of Christy Lane and Hickshill Road.

As with State Road 277, CR 277 remains along the east side of Holmes Creek, winding through farmlands and small forests of northwestern Jackson County.

In reality no such spurs exist because the route stays strictly along Piano Road.