Pittsville: Strawberry and Railroad History

Pittsville is a rural town whose history is rooted in agriculture and railroads. Its local history stretches from the early 19th-century general store to the strawberry trade and buildings that reflect different aspects of life in the area. For travelers interested in regional history, this offers several points of interest.

Local Development and Railroad History

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.” When the Wicomico & Pocomoke Railroad was completed in 1868, it brought trade and people to the Pittsville area. The store represents the town’s early commerce; the railroad later marked another boost for trade and population growth in the area.

The Strawberry Industry and Strawberry Festival

The strawberry industry vividly illustrates Pittsville’s agricultural past. Strawberry growers could ship 30 to 40 railroad cars of produce each day. Local growers established a strawberry auction in the town center, known as “Strawberry Time.” In the summer of 1923, Pittsville’s strawberry harvest filled a record 61 railroad cars. The daily figure describes shipments per day, while the 1923 figure refers to the record harvest in a particular summer. Together, these figures show two measures of the local strawberry industry.

The annual Pittsville Strawberry Festival takes place at Pittsville Town Park. For your trip planning, check the dates and program for the relevant year.

Historic Buildings and Their Stories

The town’s architectural heritage includes the Pittsville Historic District, which encompasses 128 properties. It meets Criteria A and C for listing on the National Register of Historic Places. The Pittsville Store is considered one of the most unusual and best-preserved 19th-century commercial buildings in Wicomico County. Another historic building is the Glass Hill School. Built around 1870, it is one of the few surviving one-room African American schools in Wicomico County. These buildings offer different insights into Pittsville’s past: the store represents commercial life, while the school reflects local educational history. The Glass Hill School is located at 7915 Maple Street, Pittsville, MD 21850; please check current visiting arrangements before you arrive.

The sites differ in scale and subject: the Historic District encompasses 128 properties; the Pittsville Store is a single 19th-century commercial building; and the Glass Hill School is one of the county’s few surviving one-room African American schools. When planning your trip, you can therefore choose between a historic district, local commercial history, and the story of a specific school.

Getting Around Town

Pittsville Park is between Railroad Avenue and Pearl Street; the pavilion is located there. The annual Pittsville Strawberry Festival takes place at Pittsville Town Park. For your trip planning, check the dates and program for the relevant year.

Discover more destinations: Salisbury, Fruitland.

For the broader travel overview: Wicomico.