In the colonial era, a place called Linchester was located a small distance to the east of present-day Preston. Colonel James Murray built a grist mill there in 1670, and a general store, a post office, and a few residences developed around it. The Methodist Church built a chapel close by about 1797, and that area became known as Snow Hill. In 1845, the post office was moved to a store there at the corner of present-day Maple Avenue and Main Street. Postal confusion ensued because there was another town called Snow Hill in Worcester County. In 1856, the townspeople resolved the problem by arbitrarily adopting the name Preston, apparently having been impressed by Baltimore lawyer Alexander Preston’s performance during a well publicized trial in Easton.

Construction of the Baltimore, Chesapeake, and Atlantic Railroad in 1890 marked the beginning of major growth for Preston. The railroad ran from the steamboat landing at Claiborne on the Chesapeake Bay to the Atlantic Ocean at Ocean City. Prior to the railroad’s arrival, commerce with Baltimore had been primarily by steamboat via the landing at Choptank, about two and a half miles to the south. Now, there were four passenger trains and two freight trains a day. During the years before and after World War I, it was common for twenty to twenty-five freight cars of canned tomatoes, apples, wheat, and watermelons to be shipped every day during harvest time. A 1908 edition of the town newspaper reported that Maryland packed five-twelfths of all tomatoes canned in the United States and that one-tenth of Maryland’s output was packed in Caroline County.

Canneries, box manufacturers, warehouses, hardware stores, blacksmithing, dry goods and millinery stores, groceries, restaurants, and a hotel flourished. At one time, there were sixteen canneries within seven miles of Preston; three were within the town near the railroad.

By mid 20th century, the canneries and the railroad were gone. Today, the largest structures in town are the Southern States grain elevator and storage silos. The remains of canneries and warehouses can be found if one knows where to look, but the appearance of Preston has changed. Old mansions and and houses relocated from old farmsteads stand beside new housing groups in attractive harmony, providing a thriving residential community. Some residents commute to out-of-town jobs, but many operate local businesses, farm, raise poultry, or continue the traditional life of watermen.