Just a 25-minute paddle from Robbie’s Marina is Indian Key Historic State Park. Visiting the island is like stepping back to a time when Indian Key was home to a thriving wrecking village of more than 100 people. Ruins of the former community are still visible, including the remnants pictured here of two three-story warehouses that were once the island’s largest structures.

Things have changed on Indian Key Fill since this aerial image was taken on October 7, 1987. The little harbor has been filled in with more changes projected to occur in the near future. One thing that has not changed is that Robbie’s Marina is still a must-stop roadside attraction in the Upper Keys. Image courtesy of the Wright Langley Collection and Monroe County Library Collection.

The Robbie’s property was originally home to the Starck family, who moved to the island in the 1940s. They are considered to be the island’s first permanent residents. The image, part of the Wilhelmina Harvey Collection, was taken in 1960 after Hurricane Donna delivered her tremendous blow. The Category 4 hurricane washed out the Lignumvitae Key Channel Bridge. The building prominently shown in the image is the Starck Fishing Camp bait house. Today, it is home to the Hungry Tarpon. Things have certainly changed a bit at Robbie’s since 1960.

Windley Key Fossil Reef Geological State Park is known for its abandoned limestone quarries and fossils. This image shows a warehouse once at the quarry used by the Keystone Rock Company. The quarrymen cut away the slabs of limestone that were then shipped to Miami, where the fossilized stone facades were polished to a sheen and sold as a decorative building material called Keystone. The Florida Keys Memorial, also known as Upper Matecumbe Key’s Hurricane Monument, is an excellent example of Keystone. Though Keystone is still used, the Keystone quarry ceased operations in the 1960s. Image from the Florida Keys History Center.

1960’s Hurricane Donna was the most powerful storm to strike the Florida Keys since the 1935 Labor Day Hurricane devastated the Upper Keys. The Category 4 storm caused significant damage to homes, businesses, and the island chain’s infrastructure. This image shows how the storm washed out the Tea Table Relief Bridge.

This aerial image, dated March 26, 1955, shows early development on Lower Matecumbe Key – especially in the area of White Marlin Beach and Toll Gate Shores. The image is from the Florida Keys History Center, Monroe County Library.

Walter and Ruth Starck bought the property known today as Robbie’s in the 1940s. In the summer of 1946, they started building a house. Later, Buck and his wife’s brother, Ellis Shires, built a bait and tackle store that Buck’s wife, Ruth, used to run. That store is known today as the Hungry Tarpon. Walter “Buck” Starck operated his fishing charter boat WAS (Walter A. Stark) out of the small marina. In this image, the WAS can be seen leaving Starck’s marina. Buck is at the helm, and President Harry S. Truman is sitting in the back wearing a white hat. The famed news broadcaster Edward R. Murrow is also on board the charter boat.

Before Robbie’s was Robbie’s, it was the Starck Fishing Camp. The Starck family became the first permanent Lower Matecumbe Key residents when they moved to the island in the 1940s. They first came to the Florida Keys after the 1935 Labor Day Hurricane after they purchased the Whale Harbor Fishing Camp circa 1937. Located at the eastern tip of Upper Matecumbe Key, the camp offered a dock, charter boats, cottages, and a restaurant during the busy winter season. Only the property’s gas station and bar remained open during the slow summer months. This image of the Whale Harbor Fishing Camp from the 1930s is courtesy of the Wright Langley Collection.

The second permanent resident of Lower Matecumbe Key was a fishing charter captain named Angus Boatwright. The Boatwright home can still be seen next door to the Robbie’s Marina property. His Boatwright Fishing Camp operated from the railroad fill that connected Lower Matecumbe to Upper Matecumbe Keys in the 1940s. He would later run his charter boat out of the Whale Harbor Marina on Upper Matecumbe Key.

This image of a public outhouse on Lower Matecumbe Key was taken by Arthur Rothstein in 1938. Rothstein was the first photographer employed by the Resettlement Administration. This federal agency (which later became part of the Farm Security Administration or FSA) was established by President Franklin D. Roosevelt as part of his New Deal to help farmers and displaced workers struggling through the Great Depression. From 1935-1940, the FSA sent Rothstein on dozens of photography assignments to document communities crippled by the Depression. Rothstein’s job brought him to the Florida Keys in 1938.

Once called Jewfish Bush Key and today called Fiesta Key, the island became known as Greyhound Key after the Greyhound Bus Station opened. Greyhound Bus service began operating in the Keys after the second incarnation of the Overseas Highway opened in 1938.

Art “Silver Bar” McKee was a New Jersey native. In 1937, he came to Florida. A hard-hat diver, he became known as the father of modern treasure hunting. Art salvaged wreck sites of the 1733 New Spain Fleet and displayed his treasures at his first McKee’s Museum of Sunken Treasure, one of the world’s first museums dedicated to treasure hunting. The Plantation Key building still stands at Treasure Harbor. The “Jolly Roger” flag seen on the building was discovered by McKee and is one of the few authentic pirate flags ever found. It is currently on display at St. Augustine’s Pirate & Treasure Museum.

Islamorada’s Florida Keys Memorial, also known as the Hurricane Monument, was built in 1937 to honor the 1935 Labor Day Hurricane victims. This image shows the monument under construction. It was dedicated in front of a crowd of thousands on November 14, 1937.

The eye of the catastrophic 1935 Labor Day Hurricane passed over Lower Matecumbe and Long Keys. The Category 5 hurricane took hundreds of lives and destroyed 40 miles of Henry Flagler’s Over-Sea Railroad tracks. This image, taken on January 24, 1936, shows the twisted railroad tracks at what was once a Lower Matecumbe Key flag stop called Crevallo. The train did not regularly stop at Crevallo, which did not have a formal depot but a simple railroad platform. The train only stopped at the Crevallo platform when the engineer saw a raised flag. After the 1935 hurricane, however, the train never ran again.

On September 2, 1935, the eye of the Category 5 Labor Day Hurricane roared over Lower Matecumbe and Long Keys. To this day, it registers as the most powerful storm ever to make landfall in the United States. Approximately 500 people died in the storm, including hundreds of WWI veterans brought in for bridge projects. The storm destroyed 40 miles of Henry Flagler’s railroad track and ended the train’s run between Key West and the mainland.

After the storm, hundreds of bodies were recovered. On September 6, Florida Governor David Scholtz ordered that cremation of the bodies was necessary to help prevent the spread of disease. The dead were placed in pine caskets, stacked, and burned at 24 sites between Plantation Key and Lower Matecumbe. Three sites were on Lower Matecumbe Key, one of which was located on what is today Robbie’s Marina. Two cremation sites were located on the other side of the Overseas Highway.

Before there was Doppler Radar and other modern weather forecasting instruments, the U.S. Coast Guard would drop Hurricane Warning boxes in remote areas. A Coast Guard plane flying overhead Indian Key dropped one of the boxes on the island to alert more than 20 people at a fishing camp on Indian Key. The small print on the box states: Return to C.C. Air Base St. Pete.

The eye of the catastrophic 1935 Labor Day Hurricane passed over Lower Matecumbe and Long Keys. The Category 5 hurricane took hundreds of lives and destroyed 40 miles of Henry Flagler’s Over-Sea Railroad tracks. This image, taken on January 24, 1936, shows the twisted railroad tracks at what was once a Lower Matecumbe Key flag stop called Crevallo. The train did not regularly stop at Crevallo, which did not have a formal depot but a simple railroad platform. The train only stopped at the Crevallo platform when the engineer saw a raised flag. After the 1935 hurricane, however, the train never ran again.

In the aftermath of the 1935 Labor Day Hurricane, the building identified as the Over-Seas Inn in this picture was one of the first buildings constructed after the devastating storm. It was built by the Sweeting family. For the 1936 school year, the building served as the temporary Matecumbe School. The building still stands at the edge of the Old Highway just down from the Florida Keys Memorial, locally known as the Hurricane Monument, at 81681 Overseas Highway.

In 1934, officials decided to upgrade the Overseas Highway and build a series of solid concrete bridges to eliminate the automobile ferry system. In the Upper Keys, three work camps were established to accomplish the feat, and hundreds of WWI veterans were brought in to work on construction projects. Each camp could house up to 250 workers. One was built on Windley Key, near Snake Creek. Two were built on Lower Matecumbe Key, one at the east end of the island near Robbie’s and one at the west end near the ferry terminal. The first bridge project would have connected Lower Matecumbe Key to what was called Jewfish Bush Key then and Fiesta Key today.

In 1934, three work camps were established in the Upper Keys to house WWI veterans brought to the Florida Keys to work on automobile bridge projects. One camp was at Windley Key, and two camps were located on Lower Matecumbe Key. Each base was capable of housing 250 workers. These camps were home to hundreds of veterans on September 2, 1935, the day the Category 5 Labor Day Hurricane devastated the Florida Keys.

The Robbie’s property is piled high with local history, some dating back over 1,000 years. For instance, in what is today the parking lot there were two large Indian mounds. These prehistoric sites were formed when the indigenous people piled up the discarded remnants of their food staples like fish, conch, small mammals, and other protein sources. Over the course of hundreds of years, the compost piles of dirt, bone, and shell broke down to create a fertile soil that looked somewhat like coffee grounds.

The limestone blocks used during the building of Henry Flagler’s Over-Sea Railroad and the failed attempt at building automobile bridges between Lower Matecumbe Key and Fiesta Key in 1934 were locally sourced. During the building of the railroad, the limestone was quarried at what is today the Windley Key Fossil Reef Geological State Park. In 1934, the limestone was quarried from Plantation Key, near Mile Marker 86 where the Plantation Key Weigh Station stands.

The first Overseas Highway opened in 1928. The official name was State Road 4A. While it was possible to drive a car from Miami to Key West, the road was incomplete. The road stopped at Lower Matecumbe Key and picked back up again at Big Pine Key’s neighbor, No Name Key. The 40-mile gap was bridged by an automobile ferry. This image from the Ida Woodward Barron Collection, circa 1930, shows cars lined up and waiting to board the automobile ferry at the Lower Matecumbe Key ferry terminal.

Beulah, Bonnie, and Frankee Laidlaw were raised on Pelotes Island, found within Florida’s St. John’s River. They moved to Islamorada in the 1930s and became some of the Florida Key’s premier fishing guides. During the Korean Conflict, their husbands, also fishing guides, were called to duty. According to Frankee, “We just had to keep things going so we did the guiding ourselves. We made out.” When the men returned from the war, Bonnie said, “We had a conference and decided we’d be more help out on the Gulf than over a hot stove.”

Crocodiles have been a part of living in the Florida Keys forever. Standing left to right in this image is an unknown man, followed by the brothers Phil and Al Pflueger. Al Pfluger would become widely known for his skills as a taxidermist. The gentlemen hunted down these two American crocodiles around the Key Largo area in August 1929. In case you didn’t know, South Florida, the Everglades, and the Florida Keys are the only places in the world where alligators and crocodiles coexist. Image from the Sullivan Collection at the Florida Keys History Center.

When the first version of the Overseas Highway, known as State Road 4A, opened to traffic in 1928, it was an incomplete road. The road stopped at Lower Matecumbe Key and picked up again at No Name Key. To complete the crossing required a four-hour boat ride aboard an automobile ferry. This image shows the first ferry arriving at No Name Key. The celebrated arrival came with a band playing on the top deck and a camera on the bottom deck, ready to capture the event on film. The ferry arrived with 23 cars. The image is from the Florida Keys History Center.

In 1924, the wooden Matecumbe School, located at what is the Cheeca Lodge property today, was replaced by a two-room coral rock building. Charles “Prof” Albury joined Ferran Pinder at the Matecumbe Grammar School around 1929. The Matecumbe Grammar School, pictured here, would be destroyed in the 1935 Labor Day Hurricane.

The first version of the Overseas Highway was officially called State Road 4A. Construction began in the late 1920s. When the road was finished in 1928, it bore little resemblance to the one linking the islands today. For one thing, the road was incomplete. While it was possible to drive from the mainland to Key West, the road ended at Lower Matecumbe Key’s west end (south). Forty miles away, at No Name Key, it started again. Navigating the gap between the two points required an automobile ferry.

This aerial of Lower Matecumbe Key was taken circa 1920 and looks northeast to Indian Key, Tea Table Key, and Upper Matecumbe Key. No houses are visible on the island, just the tracks of Henry Flagler’s Over-Sea Railroad. It does not appear that work on State Road 4A, the original Overseas Highway, has begun. The first version of the road opened in 1928. Photo courtesy of the Wright Langley Collection, Monroe County Library

Before it became a state park, Lignumvitae Key was transferred to the Biscayne Chemical Company, owned by William J. Matheson, from 1919-1953. The four-bedroom, coral-rock Matheson House was built in 1919. Construction was done by Reynolds Cothron and his son, Alonzo, and supervised by Henry Pinder. The small building behind the house is a freshwater cistern, with rainwater delivered to the cistern via gutters linking the two structures.

The Miami architect Walter C. DeGarmo designed the two-story, four-bedroom Matheson House on Lignumvite Key. Henry Pinder supervised the construction of the coral-rock house, built by Reynolds Cothron, in 1919. Inside, the original Dade County pine is still visible as the house has been preserved and furnished to reflect how it looked in the 1930s. Robbie’s makes visiting Lignumvitae Key Botanical State Park easy with boat service to the island every weekend.

This map shows the timetable of the Florida East Coast Rzailway. By 1908, daily service had been established between Miami and Knights Key (in bold red). The tracks between Key West and Knights Key were still under construction, and while the first train arrived in 1912, it passed over several temporary bridges. The route would not be completely finished until 1916. The map is from the Scott DeWolfe Collection at the Florida Keys History Center.

Connecting Upper Matecumbe Key to Lower Matecumbe Key was a massive project for the men employed by Henry Flagler’s Florida East Coast Railway. Instead of building bridges, the men in this image taken in 1906 are working to build the fill necessary to create a solid land bridge to connect the two islands. By 1908, the train was rumbling down the railroad tracks between Miami and Knights Key, at the base of the Seven Mile Bridge, twice daily.

The original Jewfish Creek Bridge supporting the Key West Extension of Henry Flagler’s East Coast Railway was a swing bridge. Found at Mile Marker 108, it looks a little different today. This image, taken circa 1906, shows the railroad bridge under construction.

Robert the Doll is a haunted child’s toy that lives in Key West. He might be the most haunted artifact in the Florida Keys, and it can be connected to Indian Key – if even just marginally. Robert Gene Otto was given the doll as a gift from his father on October 25, 1904, his fourth birthday. In 1875, August 2-3, Dr. Joseph Otto, Robert’s grandfather, was the attending physician at the Navy’s Camp Bell on Indian Key during an outbreak of yellow fever.

This image from the Monroe County Library Collection shows the first train arriving at the Central Supply station located on the railroad fills built to connect Lower Matecumbe and Upper Matecumbe Keys. The image looks toward Lower Matecumbe Key and what, decades later, developed into Robbie’s Marina. The photo, taken in June 1907, provides hints as to how railroad workers built the fills. It also shows the contemporary bathroom facility built out over the water.

By 1860, a sizeable Norwegian sailor named Captain Cole arrived on Lignumvitae Key. He built a small home. Described as an educated man, Cole had a bookshelf filled with books written in several languages. He also grew watermelons and sold them in Key West.

Near Alligator Reef Lighthouse, there was once a little spit of land called Alligator Key. As noted on the U.S. Coast Survey conducted by A.D. Bache (1848-1852), Alligator Key was located offshore of the Matecumbe Keys. It has been described as “…about a mile and a half long, elevated but two or three feet above the sea, and bordered with a growth of mangroves, upon which grow oysters and other mollusks.”

Did you know that the round cisterns found on historic Indian Key were built by the military after they moved their depot to the island from Tea Table Key in 1840? The military used Indian Key as their base of operations through the end of the second escalation of the Seminole War in 1842.

Charles Howe once owned Duck Key, where he had salt ponds. He also lived on Indian Key and was the partner of Dr. Henry Perrine in his Tropical Plant Company. Howe and his family were on the island during the August 7, 1840, attack at Indian Key during the Seminole War. In the wake of the attack, a handful of people remained on the island. They included Jacob Housman and his wife, the Goodyears, and the Howe family. None of them stayed for an extended period. Image courtesy of the DeWolfe & Wood Collection at the Florida Keys History Center.

August 7, 1840, was the 183rd anniversary of the attack at Indian Key. It was the southernmost attack of the Seminole War. There were approximately 50 people on the island when the violence erupted. Six people, including Dr. Henry Perrine, were killed. There may have been a seventh casualty of the attack. Perrine introduced the sisal agave to Florida where it is still growing on the island. He was buried somewhere on Lower Matecumbe Key.

Once upon a time, Indian Key was the most important island in the Florida Keys, not named Key West. This map, dated 1840, shows how developed the island was before the August 1840 Indian attack during the second escalation of the Seminole War. The map shows a proposed bridge that would have connected Indian Key to Old Matecumbe (Lower Matecumbe Key). Note that on the map, Plantation Key is identified as Long Island. Photo courtesy of the Wright Langley Collection, Monroe County Library

July 3rd marked the 200th anniversary of the creation of Monroe County. The original county stretched from Key West north to Lake Okeechobee and west to Charlotte Harbor. In 1836, Dade County was created, and all the Keys north of Bahia Honda became part of the new county. Indian Key, the largest community in the newly formed district, was declared the county seat.

Did you know that Islamorada’s iconic Alligator Reef Lighthouse was named after the U.S. Schooner Alligator, an 86-foot, 12-gun ship assigned to the storied anti-piracy West Indies Squadron that wrecked on the reef on November 20, 1822?

Matecumbe is one of South Florida’s oldest place names. In 1573, the name was written in a letter to the King of Spain. Since then, Matecumbe has always referred to two islands, Upper Matecumbe and Lower Matecumbe. For the Spanish, they were New Matecumbe and Old Matecumbe. In some cases, the names were interchangeable, with some Spanish charts identifying Lower Matecumbe Key as Matecumbe la Viejo – Old Matecumbe. The 1733 chart marking the wreck sites of the 1733 New Spain Fleet identified Upper Matecumbe as Matecumbe Viejo and Lower Matecumbe as Matecumbe Nuebo