SR 20 becomes Monticello Avenue on crossing Moores Creek into the city of Charlottesville. The street reduces to two lanes and curves west to Avon Street, onto which the state highway turns north. At Garrett Street, SR 20 continues onto four-lane divided 9th Street, which crosses over CSX's Piedmont Subdivision into downtown Charlottesville. The state highway passes to the east of the Downtown Mall and meets US 250 Business, which heads eastbound along Market Street and westbound along High Street, which are both two-way streets. The business route joins SR 20 in a concurrency on High Street, which passes by the former Martha Jefferson Hospital. US 250 Business reaches its eastern terminus at US 250 (Long Street). SR 20 turns east onto US 250 to cross the Free Bridge over the Rivanna River to leave the city limits.