The Streets of Key West: How Did They Get Their Names?

If you’ve spent any time in Key West, you know the names: Duval, Whitehead, Simonton, Fleming, Eaton, Caroline.

We drive them, bike them and walk them every day—but have you ever wondered who these streets were actually named after?

Many of Key West’s familiar street names date back to the island’s earliest days of development and offer clues to the people who helped shape the city.

Here’s a look at the history hiding in plain sight on some of Key West’s best-known streets.

Duval Street

Let's start with the one everyone knows.

Duval Street was named for William Pope Duval, Florida’s first territorial governor, who served from 1822 to 1834.

Today, Duval stretches from the Gulf of Mexico to the Atlantic Ocean and has become the heart of Key West’s entertainment district. Restaurants, galleries, shops, historic buildings and bars line the street from one end to the other.

It’s hard to imagine Key West without Duval Street—but its name reaches all the way back to Florida’s territorial beginnings.

Whitehead Street

Running parallel to Duval, Whitehead Street is another of Key West’s historic thoroughfares.

It was named for John Whitehead, one of the men closely associated with the early development of Key West after the island changed hands in the 1820s.

Whitehead Street is home to some of the island’s most recognizable landmarks, including the Southernmost Point area and the Ernest Hemingway Home and Museum.

It may be quieter than neighboring Duval, but historically, it’s every bit as interesting.

Simonton Street

Simonton Street takes its name from John W. Simonton, one of the most important figures in Key West’s early history.

In 1822, Simonton purchased the island of Key West from businessman Juan Pablo Salas for $2,000.

Simonton recognized the island’s strategic location along major shipping routes and believed Key West had enormous commercial potential.

He was right.

Key West would eventually become one of Florida’s most prosperous cities, thanks in part to industries including wrecking, shipping, fishing, sponging and cigar manufacturing.

Today, Simonton Street is a daily reminder of the man who saw the potential of this tiny island more than 200 years ago.

Fleming Street

Fleming Street was named for John W.C. Fleming, another of the original proprietors involved in Key West’s early development.

Today, Fleming is one of those streets that gives you a wonderful glimpse of everyday Old Town Key West.

Historic homes, tropical landscaping, guesthouses and neighborhood businesses line the street, making it feel distinctly different from the activity of nearby Duval.

It’s also a great example of how Key West’s earliest history continues to shape the city we know today.

Eaton Street

Eaton Street was named for John Henry Eaton, who served as a United States senator from Tennessee and later as Secretary of War under President Andrew Jackson.

Eaton was another of the original proprietors connected to the early development of Key West.

Today, Eaton Street runs through the heart of Old Town and passes some of the city’s most recognizable historic buildings and landmarks.

It’s one of those streets where simply walking a few blocks can feel like a tour through different chapters of Key West history.

Caroline Street

Caroline Street also dates back to Key West’s earliest street plan.

The street runs through an area that played an important role in the island’s maritime and commercial history, particularly near the historic seaport.

Today, Caroline Street connects some of Key West’s most familiar areas, from Old Town neighborhoods to the waterfront.

And while the origins of some early Key West street names are well documented, others—including Caroline—have stories that aren't quite as clear. That's part of the fun of digging into the island's history: there is almost always another story waiting to be uncovered.

Key West’s Streets Are a Living History Book

What makes these names so interesting is that they aren't simply labels on a map.

They connect modern Key West to the people who were here during the island's earliest years as an American settlement.

The streets have changed dramatically since the 1820s. Horse-drawn carts eventually gave way to cars, bicycles and scooters. Homes, cigar factories, businesses, churches, restaurants and hotels appeared along them. Generations of Conchs have grown up walking the same routes.

Yet many of the original names remain.

The next time you turn onto Simonton, walk down Fleming or bike along Whitehead, take a second to think about just how long those names have been part of Key West.

In a city with more than 200 years of stories to tell, sometimes you don't have to look very far to find history.

Sometimes, all you have to do is look at the street sign.

Want to discover more stories about the history, homes and neighborhoods that make Key West unlike anywhere else?

Visit KeyWestSisters.com for more about life and real estate in Key West.