Greenwood’s history can be explored through its railroad heritage: in 1858, after the Delaware Railroad was completed through Northwest Fork Hundred, the railroad station and town were laid out on land belonging to Simeon Pennewell. The station helped Greenwood quickly become a market town and business center. Alongside this historical focus, agriculture, commerce, and today’s local treats are also part of a stay here. Travelers seeking a destination with a sense of local history will find a clear timeline, complemented by seasonal offerings and farm-fresh ice cream.
Railroad, Town Planning, and Market History
The 1868 Atlas of Delaware shows Greenwood centered around the railroad: within a few blocks along the line were a station, a general store, a hotel, and homes. This snapshot adds a vivid picture of the town’s layout at the time to the founding year. It shows not only a train station, but also homes and businesses along the line.
Another period in the town’s history is the Maryland, Delaware and Virginia short line, which ran east to west through Greenwood in the 1910s. Together with 1858 and the 1868 atlas, it provides three distinct historical reference points. The station is part of the town’s beginnings, the 1868 depiction reveals its early layout, and the short line adds a later chapter.
The economic history was shaped by more than the railroad. It included orchards and row-crop farming, as well as general and specialty retail. A blacksmith shop, gristmill, sawmill, and cannery add to the picture. Agriculture, skilled trades, processing, and sales give the term “market town” a more concrete context: the station helped spur growth, while a range of activities shaped the local economy.
Ice Cream and Seasonal Offerings
Vanderwende Farm Creamery has a shop in Greenwood and makes homemade, small-batch ice cream with fresh-from-the-farm ingredients. For a treat break, it brings together artisan production and a direct connection to agriculture. As offerings may change, it’s a good idea to check the current selection before visiting.
Don’s Tree Farm Christmas Shop’s seasonal offerings include wreaths, garlands, table decorations, grave decorations, and Christmas gifts. This adds a distinctly seasonal element to your travel plans. If you have specific items in mind for your stay, check in advance to see what is currently available.
Cycling and Getting Around
Cycling on quiet back roads is another way to explore Greenwood. Road conditions and suitability can change, so check the latest conditions before setting out and choose a route that fits your plans. This keeps your plans grounded in local conditions rather than assuming a particular route or travel time.
For getting your bearings, the Greenwood Public Library is less than a mile from U.S. Highway 13. It can be reached via Market Street, Delaware Route 16, and is just before the railroad tracks at the intersection of Mill Street and Market Street. These street and intersection names provide useful landmarks when planning your stay in Greenwood.
Discover More Destinations
Discover more destinations: Millsboro, Fenwick Island, Seaford, Lewes, Milford, Bethany Beach, Dagsboro, Dewey Beach
For the overview of the wider area: Sussex County.
