Pittsville was originally called Derrickson’s Crossroads in the early 1800s, but in 1864 it was renamed in honor of Dr. Hiliary R. Pitts of Berlin who set up a general practice there while also serving as the physician for the railroad.

The railroad carried passengers and provided freight service for the area’s major cash crop—strawberries. The town’s first school was built in 1836. Ayers Methodist Episcopal Church was built in 1840 and Grace Methodist Protestant Church in 1876; the two churches combined in 1989. The post office was established in 1855, and a fire company was formed in 1927. Several businessmen incorporated the town’s first bank, Truckers and Savings Bank, in 1906. Peninsula Bank now occupies that original bank’s building.

Starting in the late 1800s, “Strawberry Time” was the town’s annual economic stimulus. Buyers would converge on the town to bid on the strawberry crop for shipment by railroad to distant cities. The town had its own hotel to accommodate the buyers. During the Depression years, strawberries were traded for other products rather than for cash, and by the latter half of the 20th century, the strawberry industry had receded in economic importance to Pittsville.

The current location of Pittsville Motors, (a Ford dealership) has been the location of an auto agency since 1915. Other businesses came and went during the 20th century—many small markets, a canning factory, nurseries, and a printing business. Pittsville is the birthplace of Drexel Truitt, who played the part of George Washington in many films in the 1930s and posed for the likeness of the General that appears on the 25-cent coin.

Pittsville is now a small bedroom community, with a few businesses. It has the characteristics of a large family because so many of the townspeople are related to each other or know each other well. It will continue to grow as development spreads from Salisbury and Ocean City.