From Hennessy (another one of a short series on some of Fredericksburg’s most prominent streets–see our ode to a changing Sophia Street here):
For more than two centuries, Caroline Street (known as Main Street for most of its existence) was the shopping Mecca for residents of the Fredericksburg region, be they borne by cars, horses, or carts. While William Street housed businesses and the occasional warehouse, Caroline was the town’s retail center, selling everything from the latest European fashions to bat guano (for fertilizer). Town council battled constantly to keep Caroline and neighboring streets pleasant for visitors and shoppers, urging 19th century residents to stop simply dumping refuse in the street and trying (vainly) to convince residents to keep hogs off the pavement–threatening to shoot or confiscate the hogs if the residents failed to comply. Finally in 1832 Council simply banned hogs in town altogether.
Parades and presidents (Harrison, Bush, and McKinley among others), protesters and Santa Claus have all frequented Caroline. George Weedon kept his tavern here, at the corner of William, and there entertained some of the greatest men of Revolutionary America, including Jefferson and Washington. One hundred and eighty five years later in a department store a few doors away, more recent patriots conducted sit-ins, seeking equality under the very laws forged by Jefferson and Washington. In the 20th century, Caroline Street assumed the aspect of a classic American downtown. Two theaters (the buildings still stand) offered the latest movies; the soda fountain at Goolrick’s Drugstore dispensed milkshakes and malts (it still does, as President George Bush noted during his visit there in 1992)), and nearby stores offered virtually everything residents of the Fredericksburg region needed (though you could no longer get guano).
Much of the upper end of Caroline above Hanover was destroyed in the great fire of 1807. You’ll find, therefore, few buildings here of anything but brick. Indeed, most of the 1000 block on the east side of the street was destroyed again in the bombardment of December 1862. But most of Caroline Street retains the character it has had for most of two centuries. A few detached older residences like the c1769 Chimneys at 623 remain interspersed among buildings that have long-held storefront businesses. Above these storefronts the owners often lived, and today apartments thrive there (the key to any successful historic downtown is to keep people living in it, and Fredericksburg has many).
At its northern and southern fringes, Caroline became residential. But the heart of Caroline retains its traditional functions, though the hogs are gone. Each year Santa hauls up the rear of Fredericksburg’s Christmas parade along Caroline, following precisely the same route traveled by President William McKinley when he visited Fredericksburg for the great meeting of the Society of the Army of the Potomac in 1900. And, every year, Santa continues to draw a bigger crowd than any of the thirteen sitting presidents who have been to Fredericksburg did during their visits.