Discover Pittsville: History Between Agriculture and Railways

Pittsville is a rural town whose history is closely connected with agriculture and the railway industry. Anyone looking for more from a trip than simply a place to stay will find a distinctive combination here of local history, historic buildings, and strawberry tradition. A holiday apartment or holiday home in Pittsville can therefore be a suitable base for anyone who wants to plan their trip around specific stories and local features.

From Derrickson’s Cross Roads to the Present-Day Town

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.” An important turning point came later with the completion of the Wicomico & Pocomoke Railroad in 1868. It brought trade and people to the Pittsville area and explains why the railway industry is part of the local history.

This development can serve as a common thread for travel planning: Pittsville represents not just a single historic site, but the connection between trade, transportation, and the rural economy. The Pittsville Store is considered one of the most unusual and best-preserved commercial buildings from the 19th century in Wicomico County. It is therefore a striking example of the town’s commercial past for travelers interested in culture.

Historic Sites and the Pittsville Historic District

The Pittsville Historic District encompasses 128 properties. Under Criteria A and C, it is eligible for inclusion in the National Register of Historic Places. The size of the area makes clear that the historical narrative relates to several properties rather than just one building. If you are looking for a holiday apartment in Pittsville, you can take this focus into account when planning your trip and orient your stay more strongly toward local history and architectural heritage.

A particularly concrete example is Glass Hill School. It was built around 1870 and is one of the few surviving African American one-room schools in Wicomico County. The school is located at 7915 Maple Street, Pittsville, MD 21850.

Strawberry Tradition with Unusual Numbers

Alongside its architectural and railway history, agriculture shapes Pittsville’s character. Strawberry farmers were able to ship thirty to forty railroad cars of produce every day. In the summer of 1923, Pittsville’s strawberry harvest even filled a record 61 railroad cars. These figures illustrate the importance of cultivation to trade and transportation.

Local growers established a strawberry auction in the town center called “Strawberry Time.” The name is part of the local tradition of the strawberry economy and supplements the factual information about the harvest volume with a distinct local designation. The annual Pittsville Strawberry Festival takes place in Pittsville Town Park. Anyone wishing to organize their trip around a local tradition can note the festival as a possible thematic occasion and check the specific event date separately.

Parks and Different Travel Interests

Pittsville Park is located between Railroad Avenue and Pearl Street; the pavilion is situated there. In Pittsville Town Park, the Phase III playground project provided for new play equipment that was intended to comply with the National Playground Safety Standards and the Americans with Disabilities Act. The wording describes a planned project and not a general statement about the current facilities. For families, however, the park can still serve as a separate point in travel planning alongside the historical topics.

This creates different areas of focus in Pittsville: You can explore the town’s history, the role of the railway, African American educational history, or the strawberry economy. A holiday apartment in Pittsville is particularly suitable for your plans if you view these topics not merely as a brief stopover, but as the guiding theme of your stay. Specific amenities, prices, and availability depend on the respective offer.

Compare More Destinations

If you would like to compare Pittsville with other places, you can also include Fruitland and Salisbury in your further travel planning. This makes it easier to decide whether Pittsville’s historic and agriculture-oriented character matches your desired vacation focus.

To the higher-level travel overview: Wicomico.