In early 2021 the U.S. Department of Transportation Federal Highway Administration added 49 routes to the National Scenic Byways Program. This was the first time since 2009. One of these is 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. This adds over 300 miles to the previous Chesapeake Country National Scenic Byway, that ran from Kent Island to Chesapeake City.

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 this part the Chesapeake Country All-American Road hundreds, if not thousands, of times. Many of these times taking photographs.

There are many wonderful sights to see on MD213 and MD18. These photos are just a few.

On the southern side of the Sassafras River is Georgetown and the location of Kitty Knight House. 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.

Chestertown is the county seat of Kent County, the oldest country on Maryland’s Eastern Shore. The town 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. When the United States completed the county’s first Census in 1790, the Population Center was near the town?

In the late 1800’s the fountain was installed in the park in the center of 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. During the period that they were closed for Covid, and the performances put on hold, work to revitalize the interior of the theatre was completed. Productions began again in October 2021 and they will be celebrating the day they saved the theatre 40 years ago from the ‘the Wrecking Bay’ later this month

Centreville is a lovely little town and it’s worth the stop to just to see the old court house.

From Centreville you’ll want to take MD18 towards Queenstown. Near the 4-H Park you’ll find 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.