Oldest Streets in Florida

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Take a ride into history on Aviles Street in St. Augustine.

Photo Credit: St. Augustine CVB

The Sunshine State’s oldest streets offer plenty of charm, shopping and history.

Florida’s history stretches from Pensacola to The Florida Keys. Many of the Sunshine State’s streets embody this rich history, offering a glimpse into Florida’s past and culture.

Figuring out the location of the oldest street in the United States is easy. It’s in St. Augustine, the oldest city in the country. On Áviles Street, pottery shards have been scientifically traced to the early 1600s. Rededicated in 2010 with representatives from its namesake Spanish town, Áviles Street today is full of galleries, quaint shops and charming ethnic restaurants.

Glamorous Worth Avenue dates to the 1920s and has long been a central part of the tony Palm Beach scene. The luxury stores, which line this throughway, rival those in any European fashion capital. It also is perfect for people-watching, surrounded by Mizner’s Mediterranean architecture. Take a stroll through the Norton Museum of Art or visit the 76-room Henry Flagler estate, Whitehall.

Like many European cities, historic Pensacola is laid out in a grid pattern. In British colonial times, Charlotte Street was the primary entrance to town from land. It was renamed Alcaniz Street in 1809.

Dozens of structures attest to its importance as a strategic military site. Around the historic plaza, the streets are all named after important figures from the Peninsular War.

On Cedar Key, on Florida’s Gulf coast, you can still follow the Walking Tour of 1884 through the restaurants and galleries on Depot and Second streets.

One of the interesting historical sites is the Island Hotel, which is listed on the National Register of Historic Places. Once an important railroad junction, today Cedar Key is a thriving artist’s colony.