Prior to the U.S. Department of Transportation Federal Highway Administration adding 49 routes to the National Scenic Byways Program, which includes the Chesapeake Country All-American Road a more than 400-mile route from Chesapeake City to Crisfield and Smith Island on country roads on Maryland’s Eastern Shore, only the portion of the Byway from Chesapeake City to the Chesapeake Bay Bridge, the Chesapeake Country National Scenic Byway, held the federal designation.

The photo above was taken from the C&D Recreational Trail on the North side of Chesapeake City featuring the bridge that cross the canal.

I am lucky that I live on the northern portion of the All American Road and have traveled and photographed this part the Chesapeake Country All-American Road many times.

On one side of the Sassafras River is Georgetown and the location of Kitty Knight House and on the other is Fredricktown. During the War of 1812, on May 6, 1813, the British under the command of Rear Admiral Sir George Cockburn attacked and burned the towns. Kitty Knight was able to meet with Admiral Cockburn and begged for him not to burn the house that an elderly woman lived. Apparently, Cockburn was suitably impressed by her efforts and withdrew his troops and the two houses were spared.

One of the many attractions in Chestertown is the Fountain in the center of the town’s park. The town, which dates back to the late 17th Century is on the Chester River and was one of the area’s earliest port towns. There are many Colonial and Victorian homes in the town that is steeped in history. Did you know that when the United States completed the county’s first Census in 1790, the Population Center was near the town?

Halfway between Centreville and Chestertown is the town of Church Hill and Church Hill Theatre. The volunteer Community Theatre for over 30 years has been providing the mid-shore area with year round quality performances of live theatre and music, educational opportunities in the dramatic arts and a summer drama camp for children.

Centreville is a lovely little town and it’s worth the stop to just to see the old court house along with the memorial statute to the county’s namesake Queen Anne.

From Centreville you’ll want to take MD18 towards Queenstown. A little pass the 4-H Park you’ll see the Queen Anne’s County Fallen Heroes Memorial which is dedicated to emergency services workers who have given their lives protecting and serving Queen Anne’s County citizens. The Fallen Heroes Memorial was first dedicated in June 2003 with stone markers inscribed with their names and the dates of these Fallen Heroes deaths.

Before you cross the Kent Narrow Bridge, the old one on MD18 not the one on US50, is the Maryland Watermen’s Memorial. The memorial is to honor those who worked as commercial Watermen.