Major highways to Annapolis include U.S. 50/301 (I-595) and Maryland Route 2/170/450. U.S. 50/301 passes on the city's west side and continues eastward over the Bay Bridge. Coming from the north, I-97 exits onto Route 50/301 just west of the city. Coming from the South, Maryland Route 2 enters the city in the Parole area, and U.S. Route 301 comes northward and joins U.S. Route 50 west of the city.
The closest major airport to Annapolis is Baltimore-Washington International, about 20 miles northwest of downtown, which has 18 scheduled carriers. Air travelers can proceed from the airport to Annapolis via Light Rail, passenger trains, limo, van, or taxi service.
The Maryland Mass Transit Administration (MTA) operates several bus routes and light rail to Washington and nearby suburbs. Carolina Trailways operates limited bus service through nearby Baltimore and Glen Burnie, and Greyhound also provides bus service. Amtrak offers rail service to Baltimore's Penn Station, and Union Station in Washington, D.C.
Annapolis's main east-west thoroughfare is West Street, also known as Route 50. Radiating northwest and southeast from downtown's Church Circle is Duke of Gloucester Street. College Avenue runs northeast from the circle.
Annapolis Transit has five bus routes that serve more than 180 stops throughout the city and the Eastern Shore area, including stops at Annapolis Mall, Anne Arundel Medical Center, and many area hotels. There are also commuter shuttles from downtown to nearby Kent Island and to the Navy-Marine Corps Memorial Stadium. Gasoline-powered trolleys run within the central business district. Several taxi and limousine companies also serve the city. Local waterways are served by the Jiffy Water Taxi, which can be picked up at the water-front. Bicycles are a welcomed form of transportation in Annapolis. The city offers several designated bike routes that use a combination of grade-separated trails and city streets. Most city buses have bike racks. Helmet use is encouraged for bicycle riders in the city, and visitors to the U.S. Naval Academy are required to wear helmets there.