When Middletown’s signature event, the Olde-Tyme Peach Festival, takes place on Saturday, August 16, it will be much more than a celebration of an important chapter in the town’s history. The festival also showcases Middletown’s lively present and the bright promise of its future.

Thousands of people from all over the region now consider the festival a tradition, and there are a wide variety of activities and attractions centered on Main Street for everyone to enjoy, but the festival also offers an opportunity to learn a little about Middletown’s history.

Middletown, as its name suggests, has always been in the middle of things—even before it became a large peach producer.

The history of Middletown can be traced all the way back to 1675, when Adam Peterson took on warrants for the land which later became the town of Middletown. The first survey of the area was completed by 1678. Peterson passed away and his widow later married David Witherspoon, a native of Londonderry, Ireland, who established the Witherspoon Tavern that was built sometime around 1761 or 1762. A small village grew up around the tavern over the next few decades.

Middletown was one of the old Delaware towns that is not on a navigable waterway. Situated just 24 miles south of Wilmington, Middletown was an early crossroads town, a tavern stop about halfway along a cart road that extended across the peninsula between the Appoquinimink Creek in Odessa, Delaware and Bohemia Landing in Maryland. 

The arrival of the railroad, in the middle of the 19th century, changed the course of the town’s history dramatically—it became much easier to ship agricultural products throughout the region. By 1861, the town of Middletown was officially incorporated. The first town council decided that Middletown should be one square mile, starting at one corner of the crossroads and extending one-half mile in each direction. This gave early Middletown a diamond shape, and it was known as the “Diamond Town of the Diamond State.”

People and Peaches

There are many facets to the Diamond Town of the Diamond State. One facet is the fruit industry that brought great prosperity to the area for several decades in the last half of the 19th century. It would be hard to overstate the importance of peaches to the history of Middletown.

The Middletown Historical Society maintains a virtual exhibition titled “People and Peaches: The Peach Industry in Middletown” on its website at middletowndehistory.com. The Middletown Historical Society was founded in 1985, born from the grassroots effort to save an historic structure called Greenlawn. 

Greenlawn was built in 1810 by Outten Davis, a founder of the Middletown Academy. William Brady later changed the outside of the home to reflect the style of the Victorian period. Greenlawn was demolished in 1985, but its farm manager’s house was saved through relocation. Since its founding in 1985, the Middletown Historical Society has hosted house tours as well as lectures on the history of Middletown.

Peaches, the virtual exhibition notes, were a cash crop that brought both work and wealth to residents of the Middletown area. The fruit had to be picked, packed and shipped so there was a need for a lot of workers. When the railroad came to Middletown, the local farmers could ship their produce to large markets like New York City and Boston.

Some of the most prominent families in the history of Middletown were involved in the peach industry. 

The virtual exhibition explains that prominent Middletown families like the Claytons, the Cochrans, and the Shallcrosses showcased their peach wealth through buildings and personal items. Their grand houses tell the story of the peach industry and its impact on Middletown.

The Cochran name is well known in the Middletown area. John Price Cochran, a governor of the state of Delaware, built the Cochran Grange in the 1830s. In the 1850s, the Cochran family grew 10,000 peach trees across three farms. The Cochran Grange is listed on the National Register of Historic Places and is still there today. 

Benjamin Biggs, also a governor of Delaware, owned farms in Delaware and neighboring Maryland with approximately 67,000 peach trees by the 1880s. His home, the Biggs Town Home, is also still there today.

Peaches also offered a path to prosperity for some local workers who started out with very little. “People and Peaches: The Peach Industry in Middletown” explains that one example of a person who used peaches to improve their life is Samuel Jones, a self-educated African-American farmer. He was born in 1841 and in the early 1860s he started working for Serek Shallcross, one of the largest peach growers in Middletown. Peaches enabled Samuel Jones to raise his family up from tenant farmers to land owners and respected members of the local community. Jones started renting a farm in 1869, which would turn out to be one of the biggest years for peaches. Over the next three decades, Jones came to own three farms of his own.

The prosperity of the peach industry was profound—but also short-lived. By the late 19th century, Delaware peach trees were attacked by diseases known as “the yellows” and “Little Peach,” the virtual exhibition explains. The thriving peach industry declined rapidly, and peach orchard owners and workers alike had to adapt to the changing landscape. It’s been a long time since peaches were a leading industry in the area, but the signs of the positive impact that the industry had on the town can still be seen today.

Middletown Academy and its long history

In 1960, the town of Middletown acquired Middletown Academy, certainly one of the most historically significant buildings in the town’s history. The building has served many purposes during its life. The Middletown Academy traces its roots to 1824, when area residents petitioned the Delaware General Assembly for a lottery to erect a building for education and public worship. Construction of the Academy began in 1826 and was completed the next year.

According to the Delaware archives, the Middletown Academy served as the center of community activities for many years. It was a building for private education, and in 1840, there were 33 students who were taking classes there. It became a part of the public school system in 1876, and it was utilized as a public school until 1929. Eventually, in 1945, the building was deeded to the St. Georges Hundred Historical Society, an organization formed to ensure its preservation. 

A key development in ensuring that the Middletown Academy continues to serve a positive purpose was the acquisition by the town of Middletown. The facility has been utilized by the town and a number of community organizations in the decades since—it has been the town hall and the home to the Middletown Chamber of Commerce, Middletown Main Street, Inc., and the Middletown Historical Society at various times throughout its history. It was officially listed on the National Register of Historic Places in 1972.

Middletown steps into the spotlight

The Everett Theatre debuted on November 9, 1922, continuing the town’s long history of having a performing arts center of its own.

The St. Andrew’s School was founded by A. Felix du Pont, a member of the famed du Pont family, in 1929. The school was founded to provide a top education for boys of all socio-economic backgrounds, regardless of their families’ ability to pay. St. Andrew's School was originally a boys’ school, but became coeducational in 1973.

Six decades after the Everett Theatre and the St. Andrew’s School made their debut, these two important Middletown institutions played a pivotal role when Middletown stepped into the Hollywood spotlight.

Dead Poets Society is an acclaimed 1989 coming-of-age drama that was directed by Peter Weir. Robin Williams, Ethan Hawke, and Robert Sean Leonard starred in the movie. It was filmed almost entirely at the St. Andrew’s School, which served as the prestigious Welton Academy in the movie. The cinematic theatre scene in the movie was filmed at the Everett Theatre on Main Street in downtown Middletown. St. Andrew’s School also served as the filming location for the young Josiah “Jed” Bartlet’s boarding school in the highly respected “Two Cathedrals” episode of The West Wing.

The Olde-Tyme Peach Festival is the perfect opportunity to enjoy a few of the many facets of the town. From the peaches to the Middletown Academy to the Everett Theatre to the nearby St. Andrew’s School, there is a lot of history intersecting in Middletown.

More information about the Middletown Historical Society can be found at www.middletowndehistory.com.

For updates about the 32nd annual Olde-Tyme Peach Festival, including the most up-to-date information about events and activities, visit the event’s website at middletownpeachfestival.com.