Chesapeake Beach was established as a resort community at the end of the Chesapeake Beach Railway, a short line railroad from Washington, DC.
The neighborhoods of Baylake Pines and Baylake Beach hug the east side of the community, although the popularity of the Chicks Beach area has those in Ocean Park claiming a piece of it as well.
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The Chesapeake Beach Rail Trail (sometimes referred to as the Chesapeake Beach Railway Trail) is a set of short trails along the original Chesapeake Beach Railway route from Washington, D.C. to Chesapeake Beach, Maryland.
Plans are underway to develop this portion of the trail and connect it to residential communities within the vicinity, providing off-road access to the towns of Chesapeake Beach and North Beach and their in-town boardwalks and trails.