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The Delray Beach Historical Society Historical Image Gallery

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The People of Historic Delray

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The first decade of farming in Delray saw the transition from mostly pineapple farms to more successful tomato crops. This wagon is loaded past capacity with crates of tomatoes. The Snider Catsup Company later opened a plant in Delray.

Historic photo of a Delray Beach pioneer seated on a horse-drawn wagon stacked with wooden crates, showcasing early Florida agricultural transport.

Pioneer Farmer with Horse-Drawn Produce Wagon

Chase & Co Tomatoes on a Merchant Wagon c. 1900s

First a full-time operation for shipping pineapples (up to ten railroad freight cars per day), the Delray Canning Company also shipped canned pineapples, tomatoes and other produce to markets nationwide.

Henry Sterling's Delray Canning Company c. 1910s

The Orange Grove House of Refuge was the first building in the area in 1876 and was used by the "Barefoot Mailman" for his overnight rests while delivering mail up and down South Florida's coast. The US Lifesaving Services built 5 refuges along Florida's coast as shelters for shipwrecked sailors. Its name comes from the Orange Grove Haulover, the first "place name" in the area, where a sour orange grove was located and where native Indigenous peoples would haul their canoes between Indian Creek and the Ocean.

Orange Grove House of Refuge c. 1890s

After the Atlantic Avenue bridge was constructed in 1911, it allowed easy access to the beach. These girls wearing their Delray High School uniforms posed for the photographer on the bridge.

High School Girls on Atlantic Ave Bridge c. 1920s

The Clark House c. 1910s

In the 1920s, Delray was known as "The Ocean City" and many businesses had the same name, including the lumber company and obviously the local garage.

Ocean City Garage Tow Truck c. 1920s

Considered the oldest home in Delray Beach, the Sundy House was home to John Sundy, who was mayor of Delray four separate times. It is a Queen Anne style home and was completely restored in 2025 as part of the "Sundy Village" development. The original home, built before electric power came to Delray, included a windmill and water tower.

The Sundy House c. 1914

Delray's first theater was the Bijou, later named the Roxy. First run movies were screened in this building on Atlantic Avenue for decades, one block east of Swinton Avenue.

The Bijou Theatre on Atlantic Ave c. 1920s

Adolf Hofman's farmhouse was a few blocks north of Atlantic Avenue, just east of Dixie Highway, the only road from West Palm Beach to Miami. This photo was taken in front of the Hofman home with a view to the north, the "highway" to Boynton Beach five miles away.

Dixie Highway Near The Hofman Homesite c. 1910s

The Delray School, built in 1913, became The Cornell Art Museum in 1990. It is located on the Old School Square campus at the corner of Atlantic Avenue and Swinton Avenue.

Flag Raising at The Delray School (Now Cornell Museum) c. 1913

Before automobiles, families would travel to the beach in Delray with a horse and buggy. This photo was taken at Atlantic Avenue and the oceanfront before any streets were paved.

A Pioneer Family Arriving at The Beach c. 1900s

Atlantic Avenue Looking West Through Downtown

Built in 1902 by John Shaw Sundy, the first mayor of Delray Beach, the Sundy House is the oldest house in the city. It was built on the highest land in the area, which was then covered with pineapple groves. The house is made of Dade County pine and has a solid wood frame.

The Sundy House c.1900s

After the first group of farmers bought land and planted crops, the Delray area quickly became the agricultural capital of South Florida. This was the first packing house in the area, owned by Henry Sterling.

Local Packing House in Delray c. 1900

Arriving in Delray when she was just three months old, Annie Hofman became an iconic figure in the area. She produced her father's award-winning produce displays at the annual fair and was one of the first schoolteachers in Delray. This photo was taken at Sundy Farms, about five miles west of Delray.

Annie Hofman at Sundy Farms c. 1900s

Black wool "bathing costumes" were the only option for people to enter the Atlantic Ocean in Delray's early days. Then as now, and thanks to the Gulf Stream current, the water temperature never dips below 70 degrees.

Pioneers