Thank you for visiting Pittsville’s Town History page. Pittsville is a rural town in Wicomico County, situated east of Salisbury, MD with a rich history rooted in agriculture and railroad industry. Click here for a quick summary of our town in an infographic format!
Early development of Pittsville began in 1834 with the opening of Levin Derrickson’s general store. The area became known as Derrickson’s Cross Roads. In 1848, a charter was issued for the development of the Wicomico & Pocomoke Railroad. This railroad would ultimately put Pittsville on the map.
In 1855, a post office was established, with Mrs. Mary Farlow being the area’s first postmistress and Mr. James Fooks, the town’s first postmaster.
W & P Railroad Bolsters Business
In 1868, the Wicomico & Pocomoke Railroad line was completed, bringing business and people to the area. Both freight and passenger service began, linking “The Crossroads” to Salisbury and Ocean City. Dr. Hilary R. Pitts was a general practitioner from Berlin and also served as the railroad company’s president. Through his leadership in the company, the town name, Pittsville, was born.
By 1877, the atlas published a map of Pittsville, boasting four general stores, two churches, a hotel, lumber mills, a cabinetmaker, and a physician.
With the construction of the railroad, strawberry farmers were able to ship thirty to forty railcars of produce per day. While strawberries were the main crop of the town, there were other businesses bringing Pittsville to the forefront as well. Lumber, hatcheries, dry goods, and a grain house were all successful industries in town.
A “Boom” of People and Businesses in Town
Booming industry brought in an influx of people. In 1889, Ayers M.E. Church opened its doors. Shortly after, in 1905, Pittsville Central School opened. The school educated elementary through high school students until 1936, when a new school was built due to an increase in student population.
In 1906, Truckers & Savings Bank opened. The bank was built with “strawberry money.” In the same year, Mr. Leamon Tingle opened his printing business in town. Three years later, gas street lanterns were installed in town.
Refrigerated railcars came in 1910, changing the game for strawberry farmers. Local growers also established a strawberry auction downtown, known as “Strawberry Time,” attracting more buyers. Buyers would stay at the Dennis Hotel, located on Main Street, and then head down to the auction. In 1913, Pittsville was in the local press with the headline, “Prosperity of Pittsville, The Strawberry Crop Brought Big Money to Growers, Best Year in the History of the Industry.” Farmers received at least $200,000 for their strawberry crop that year.
While strawberry farming was booming, Pittsville also acquired its first automobile dealership (c. 1912). The dealership sold Fords, Buicks, and Maxwells. With the construction of Old Ocean City Road in 1914-15, housing and business development grew. Ford and Chevrolet both opened up dealerships.
In the 1920s, a tomato canning factory on the north side of Railroad Avenue provided more growth and industry for the town. Owners of the canning industry included the Jones, White, and Wimbrow families. Tom and Benny Middleton had greenhouses, and operated the Middleton Florist Shop around this time frame. Strawberry farming reached its peak growth season during the summer of 1923, having enough strawberries to fill a record 61 railcars.
Drexel Truitt, a Pittsville local, took his Pittsville roots to Hollywood. He was most famous for his likeness to President George Washington. He posed as the silhouette for the quarter coin. In 1927, he took on the stage name David Ward, and played many roles as George Washington in films. Famously known as the “pickle shed,” T.W. Davis Co. had a packing plant that brought in roughly 45,000 cucumbers and peppers each year. Cucumbers would then be distributed as far away as Texas, Nebraska, Colorado, Illinois, and Massachusetts. The pickle shed would become a source of employment for local teens in future years.
In 1927 a committee was created to assess the need for a fire department in town. By 1928, Pittsville’s Fire Department was established, followed by the construction of the first fire hall in 1929. The first officers of the fire company were T.W. Davis, Walter H. Farlow, James W. Brittingham, and Southey Truitt.
Electricity was installed in the town in 1929. The fire department installed its first electric sign in 1932. In the 1930s and 1940s, Allie Hamblin had a holly-wreath making business, where at its peak, over 100,000 wreaths were sold during the year. Tingle’s Nursery also grew, having one of the largest catalogs. Tingle’s would continue to be popular through the 1970s.
By 1945, Pittsville became incorporated. This allowed the town to tax residents in order to install a stoplight and begin trash collection. The Pittsville Lions Club was organized in October of 1945, with its first president being James R. Truitt. Essel T. Farlow took over the following year, and also worked as the zoning chairman for the town. Lester Brittingham, the third president (1947-1948), helped in the construction of the Lion’s Club building.
Disease and the Railroad Demise
In the 1940s, two events negatively impacted the town of Pittsville. The first was “Red Stele” disease, which wiped out most of the berry varieties, devastating the once booming strawberry farming industry. This hardship affected all of Wicomico County’s strawberry farmers.
The second negative event was the national dismantling of the railroad industry, which ultimately led to the closure of the railroad in town. While the railroad officially closed in 1955, by 1948, it had dwindled to only 56 employees (in former years, there were roughly 600 workers).
A town that endures
The town of Pittsville endured. The new Pittsville Motors opened in 1955 and was successful in the automobile industry. In 1957, over 40 stop signs were placed at intersections of streets. Six 30 mph speed signs were posted.
Howard Powell opened a restaurant, “Addie’s Lunch Room,” in the late 1960s. It was then renamed the “Hitching Post” until it was bought by Charles and Ruth West in 1978. The West family renamed the restaurant again, this time calling it the “Pittsville Diner.” Dave White then owned and operated the diner for 28 years.
In the 1970s, a new firehouse was built. In 1972, Hollywood came to Pittsville to film “The Rimers of Eldritch,” starring an up & coming Susan Sarandon. In 1982, a town water system was installed. Jim Jackson moved to Pittsville in the 80s and opened “Jackson’s Floral Designs.” Jackson would later go on to lead the town in several restoration projects to preserve the town history.
In 1990, Foot Management brought its business from Salisbury to Pittsville. One year later, Taylor Oil Co. built a local gas station, and Trent Molnar opened JT’s inside shortly after. By 1995, the book, Pittsville: An Eastern Shore Town’s History, was published. Today the town has roughly 1500 residents and several local businesses.
Come visit town hall or the Pittsville Library (located next to Pittsville Elementary School) to learn more about the town’s history… or strike up a conversation at a local restaurant with some of the direct descendants of our founding families including:
The Adkins family / The Davis family / The Farlow family / The Fooks family / The Hearne family / The Lewis family/ The Littleton family / The Middleton family / The Parker family / The Parsons family / The Tingle family / The Truitt family / The West family / The White family
“A Pictorial History of Pittsville” by James Jensen / “At the Crossroads” by Paul Baker Touart / “Pittsville: An Eastern Shore Town’s History” by Louis (Casey) Parsons / Maryland Historical Trust / Interviews with Jim Jackson / Article review with Trent Molnar / Countless others who have contributed to the town’s history over the years
Other before and after images of our town:
Old Railroad Station is restored
Tapestries and old photos of the trains coming in and out of town
Pittsville Full Gospel Church and Ayers United Methodist Church
Pittsville’s Police Department, Boxcar 40 (Voted Best New Restaurant in Coastal Style 2019), and other restored areas in town