St. Augustine Old Town Running Route

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Length up to 5.3 km (3.3 miles), terrain flat

For more running routes, see the Route List

St. Augustine is not only the oldest continuously occupied city in the US, it is also one of the most beautiful. And one of the most touristy. So the best time is to run is in the mornings, before all the tourists are wandering about the lanes and all the cars are out clogging the streets. Mornings also happen to be the coolest time of day, which is another big plus.

Like most people, I fell in love with St. Augustine the first time I laid eyes on it, about 40 years ago. The small, old houses with their jungley gardens fascinate me every time.

Fountain in St. Augustine

There are wide vistas over sparkling Matanzas Bay, dominated by the massive fort, Castillo de San Marcos. The bay is full of marinas and is crossed by the Bridge of Lions, with its elegant towers. There is an old-town packed with interesting old buildings at every angle. There are the fantasy-world Spanish-revival hotels built by railroad magnate Henry Flagler. And there are nearby leafy Victorian-era neighborhoods of quiet, elegant streets and front-porch swings, many of them bed-and-breakfasts.

Matanzas Bay at the fort

The town is home to musicians and poets, fishermen and drunks. And they are all held captive by the ghosts of history hovering in the shadows of the quiet lanes. Florida Indians, the Spanish, the English, slaves and freedmen, confederates and yankees have all added their lives and their stories to these streets over the centuries.

Here's a route that follows the main sights through the old town and waterfront, past many of my favorite spots.

The St. Augustine Old Town Route
Any proper route should start in the heart of town, in the old square on Cathedral Place, full of tropical plants and old oaks dripping with Spanish moss. The old Government House (now a tourist information center) is to the west, and the cathedral to the north.

Old St. Augustine stretches north/south along the bayside, and is just a few blocks wide. We'll run up and down this narrow stretch.

Starting point obelisk, with Government House: run to the cannon and turn right!

Start at the obelisk in the square. We will turn north to run up the little pedestrian lane, St. George Street. This is the town's most touristy street, so there are a lot of others underway if you get here at the peak times (shopping hours). You might have to dodge tourists, but it's worth the effort.

Head past the ever-changing mixture of stone- and wooden-shops and restaurants, including the oldest wooden schoolhouse in the US. The street ends at the north end of town, at the stone city gates.

Along St. George Street

Turn right and run the 100 meters to cross the large street, Castillo Drive. Continue running straight towards the old fort, along the dirt path next to the reconstructed town wall. When you get to the outer ramparts of the castillo, turn right and circle the fort. The castillo was built by the Spanish in the late 1600s to protect themselves from English pirates. The fort is now a national monument, and can be visited inside during the daytime if you buy an entrance ticket.

The Castillo de San Marcos

Run back to the old city gate again, but keep going straight west on Orange Street to the next chance to turn left, on Spanish Street. You are now heading back south, parallel to St. George on this narrow street with its little wooden houses.

The city gates at St. George Street

When you get to Hypolita Street, turn left to cross eastwards through the old town.

At Charlotte Street, turn right and head south again. This is another nice old street, less touristy than St. George, but there is some car traffic. Just as you come back to the town square, you'll pass the Trade Winds Lounge, my favorite evening hangout for live music. The Bridge of Lions spans the bay to the left.

Continue along the east edge of the square, and you'll see an old covered market. It looks like any old European market for fish or meat, but this one sold people: it was the town's slave market. Slaves were brought into the town from its first days of existence, when the town was founded in 1565, and the practice continued for 300 years. Only a plaque reminds us of the spot's sad purpose.

The square, with slave market in background

Now turn right and run westwards through the square. The old cathedral is on the right side. The present one replaced several earlier ones which had all burnt down.

Cathedral Place ends at Flagler College, where you turn left, then right to get around the main building and continue running westwards along its front side on King Street. This fascinating building was originally built as the Flagler Hotel, from Florida's earliest tourism days. Back then, 100 years ago, every new Florida town was built in the Spanish style. This one was built very baroque, with lots of odd Moorish decorations.

Flagler College

At the main entrance, it's worth it to run into the main courtyard and take a look around at the amazing decor.

Come back out and then cross King Street across the square to the Lightner Museum, in another fantastic old hotel in the Spanish style. Back then it was the Hotel Alcazar, another Flagler project. The same architect later designed the NY Public Library at Bryant Park, one of my favorite places. The Lightner contains mainly American antiques.

Lightner Museum

Run southwards past the museum along Cordova Street, until you come to a red-brick path to the left, Palm Row. Follow Palm Row the one block back to St. George Street, where you turn right to follow it southwards towards the south end of the old town.

St. George here is full of Victorian-era homes with jungley gardens. You'll also pass St. Joseph's Convent on the left. The St. Francis Bed & Breakfast is also on the left, with its inviting courtyard. It's a bit pricey, but well worth a stay (we splurged and stayed there on my last visit, in contrast to my first visits when I had to hitch-hike to St. Augustine to visit a girlfriend).

St. Francis Inn front porch

After a while, St. George Street opens up on the right side along Maria Sanchez Lake. This was once a swampy creek, but was dredged out to build up the land for the Lightner Museum further to the north.

St. George Street ends at South Street, and across the street you can see the rest of Maria Sanchez Creek winding its way through a swampy estuary into Matanzas Bay.

Jasmine on a St. Augustine garden wall

Turn left and head two blocks east to Marine Street, where you turn left and run back northwards past more nice old houses and their flowering gardens.

You'll pass St. Augustine National Cemetery, where US soldiers from the Seminole Wars are buried. Under the stone pyramids are the remains of Major Francis Dade and his 110 men, who were ambushed by Seminole warriors on a march across Florida.

Next comes the National Guard buildings at St. Francis Street. If you look left, you'll see the flags flying at the oldest house in the US, now a museum. It is well worth a tour. But now, keep to the right and run directly along the water on Avenida Menendez.

The oldest house in USA

You'll pass the old stone house and beautiful terrace of O.C. White's seafood restaurant, across the street from the municipal marina.

Then you'll come to the town square again at King Street, where you turn left and run back through the square again to the obelisk.