City Escape: Annapolis, Maryland

City Escape: Annapolis, Maryland
This journey immerses travelers in Maryland’s colorful history and the tranquil ambiance of a landscape surrounded by water. The laid-back charm and coastal culture makes southern Maryland feel thousands of miles removed from the frenetic pace of nearby Washington, D.C. And there’s lots of fresh seafood to enjoy at the many good restaurants.


Approximately 194 miles

Meet-up Spot

Starbucks, 2498 Solomons Island Rd, Annapolis, MD

Lunch Stop

Charles Street Brasserie offers tapas in a cozy waterfront atmosphere, complete with live piano music. Find it at 120 Charles St, Solomons, MD, (443) 404-5332.

Scenery (3 out of 5)

Much of the interior landscape is heavily forested or under cultivation. Majestic views of the Potomac River, Chesapeake Bay, and their countless inlets and harbors, however, are inundated with all manner of sailing and motorized pleasure craft.

Traffic (3 out of 5)

Traffic is mostly light on the two-lane roads. The north/south main transit routes through this watery, dissected landscape are more heavily-trafficked multi-lane throughways, which often can’t be avoided.

Difficulty (2 out of 5)

The route is not technically difficult and is appropriate for most bikes and riders. Some sections are curvy and heavily shaded by overarching tree limbs. Approach these roads carefully, especially when entering them after riding in bright sunshine.

Road Conditions (3 out of 5)

With few exceptions, the roads are in very good condition and vary from multi-lane highways to narrow passages with no centerline.

Points of Interest

John Wilkes Booth Escape Route
After assassinating President Lincoln in April 1865, Booth fled south through Maryland. Historical sites include Surratt Tavern, the Dr. Mudd House Museum, Huckleberry Farm, Dent’s Meadow, and Pope’s Creek, where Booth and his accomplice David Herold crossed the Potomac into Virginia.

Historic Port Tobacco Village
Port Tobacco, which was settled in 1634, was once Maryland’s second largest seaport. The history of this village includes Native Americans, colonists, revolutionaries, assassins, spies, and more. During the Civil War it was a beehive of Confederate activity.

Historic St. Mary’s City
This was Maryland’s first colonial settlement and capital. The state-run historic area, a reconstruction of the original colonial settlement, is a living history campus that includes a museum complex and St. Mary’s College of Maryland.

The Calvert Marine Museum
This museum, with its exhibits, programs, lighthouses, and boats, showcases the maritime history and ecology of southern Maryland. Aquariums display the aquatic life of the Chesapeake estuary.

The Chesapeake Beach Railway Museum
The museum recounts the history of this short line railway, which transported sunbathers from Washington, D.C., to the resort town of Chesapeake Beach, MD.