Pittsville combines a history rooted in agriculture and railroads with distinctive historic buildings. For travelers interested in local history, traces of strawberry harvesting and rail traffic lead to a Historic District, a former one-room schoolhouse, and a 19th-century commercial building.
A Local History Connected to the Railroad
Pittsville’s early development began in 1834 with the opening of Levin Derrickson’s general store. The area became known as “Derrickson’s Cross Roads.” The Wicomico & Pocomoke Railroad was completed in 1868, bringing commerce and people to the Pittsville area.
Pittsville’s railroad history is closely connected with agricultural commerce.
Strawberry Harvest and Strawberry Time
Local growers established a strawberry auction in the town center, which was called “Strawberry Time.” Strawberries were also part of a major shipping business: strawberry growers in Pittsville could ship thirty to forty railroad cars of produce each day. In the summer of 1923, Pittsville’s strawberry harvest filled a record 61 railroad cars. The daily shipments and the record set in one particular summer illustrate different aspects of this agricultural past.
The Pittsville Strawberry Festival takes place annually at Pittsville Town Park. If attending the festival is part of your trip, check the dates and program for that year’s event. This lets you plan your trip around a specific event date rather than assuming a particular current program based on the historic strawberry tradition.
Historic District and Individual Buildings
The Pittsville Historic District includes 128 properties and meets Criteria A and C for listing on the National Register of Historic Places.
Individual buildings offer specific examples that add to this picture. Glass Hill School was built around 1870 and is one of the few surviving African American one-room schoolhouses in Wicomico County. Its address is 7915 Maple Street, Pittsville, MD 21850. If you plan to visit, confirm the visitor arrangements before you arrive. Pittsville Store is considered one of the most unusual and best-preserved 19th-century commercial buildings in Wicomico County.
Getting Around and Planning Your Stay
For finding your way around town, Pittsville Park is located between Railroad Avenue and Pearl Street; the pavilion is there. The festival venue is identified as Pittsville Town Park.
When choosing Pittsville as a destination, you can focus on what interests you most: the history of strawberry growing and railroads, the historic buildings, or the annual festival. For specific visit planning, be sure to consider the visitor arrangements for Glass Hill School and the festival dates and program.
Discover more destinations: Fruitland, Salisbury.
Return to the main travel overview: Wicomico.
