The National Pike Festival and James Shaull Wagon Train Foundation annual 2022 event. Starts Friday, May 20 in Clear Spring, MD and ends Sunday, May 22 in Boonsboro, MD Shaffer Park. Wagon trains have been rolling since 1989 as a part of the Maryland segment of the Washington County National Pike Festival. With its strategic geographical location between the Allegheny Mountains and the Blue Ridge Mountains, Washington County played a key role in opening the West to our nation.